10. ORGANIC CHEMISTRY---XC

Learning Outcomes Organic Chemistry
By the end of this chapter, you will understand
Chapter - 10
 Allotropy of carbon  Classification of organic compounds based on
9
 Vital Force Theory type of functional group
 Reasons for the formation of large number of compounds  Nomenclature
 Hybridization  Basic Rules of Nomenclature
 Classification of organic compounds based  Nomenclature of Alicyclic Compounds
on structure  IUPAC Names of Polycyclic Compounds
 Classification of organic compounds based on type  Isomerism
of bond present  Structural Isomerism
 Homologous series  Stereo Isomerism
 State of carbon in carbon compounds
1. Introduction Complex compounds : With hydrogen, nitrogen
Carbon is a non- metallic element that has been and sulphur, carbon forms complex compounds in
known since ancient times in the form of coal, plants and animals.
charcoal, graphite and diamond. Its importance In natural water: The carbon dioxide dissolved
arises from the fact that in combination with other in water exist as carbonic acid.
elements it makes up the living tissues of all living Carbon is also an important constituent of a wide
plants and animals. There are over 1 million known variety of industrial and commercial products like
carbon compounds. sugar, paper, leather, marble, petroleum, silk,
medicines, insecticides, dyes and perfumes.
The study of chemistry that deals with the study
Isotopes of carbon : The most common isotope
of carbon compounds made by and derived from
of carbon is carbon-12, it was adopted as the
living organisms is called organic chemistry. The
standard for atomic weights and was assigned
study of all other compounds is grouped under weight of 12.
inorganic chemistry. i) Carbon-12 accounts for almost 99% of
Several forms of carbon are also important naturally occurring carbon.
sources of energy. ii) Carbon-13 accounts for most of the rest.
Occurrence of carbon : iii) Carbon-14 radioactive isotope, occurs only
Carbon is one of the very select group of elements in traces. It is used by scientists in
that can exist free in the nature. determining the age of pre-historic objects.
In the elementary state, carbon occurs as diamond,
graphite and amorphous carbon. 2. Allotropy of carbon
In the combined state it occurs as follows : Allotropy : The property by virtue of which an
Oxides : CO 2 (0.03% by volume in air) and CO element exists in more than one form in the same
that occurs in volcanic gases and in furnace gases. physical state, having the same chemical properties
Carbonates: Limestone-CaCO3, but different physical properties, is called allotropy.
Magnesite- MgCO3; Reasons for allotropy :
Dolomite- CaCO3 . MgCO3 ; a) The different methods by which each form
Calamine- ZnCO3. is or was prepared.
b) Different atomic arrangements in the
Hydrocarbons : Methane, acetylene, benzene,
molecules of each form.
petroleum, natural gases etc.
c) Different amounts of energy associated
with each form during preparation.
384 10th Class Chemistry
Carbon exhibits allotropy. Diamond, graphite, C60 Preparation of urea : In 1828, a German scientist,
are some important allotropic forms of carbon. Friedrich Wohler (1800-82) obtained urea (a typical
In diamond, carbon atoms are arranged in organic compound and product of the animal
tetrahedral structure. Each carbon is attached to metabolism) by heating an inorganic compound
four other carbon atoms. In graphite, carbon ammonium cyanate or a mixture of ammonium
atoms are arranged in hexagonal structure. Many sulphate and potassium cyanate.
heat
hexagons form a graphite layer. C60 , buckminster NH4CNO  NH2 .CO.NH2
ammonium cyanate Urea
fullerene, is a football like structure containing
pentagonal and hexagonal rings.  
NH4 2 SO4  2KCNO
potassium cyanate
Carbon forms two types of oxides, viz., CO ammonium sulphate
and CO2 . heat

 2NH4CNO  K 2SO4
CO is a poisonous gas. CO2 is a fire extinguisher..
rearrangement
Plants absorb CO2 for photosynthesis. Solid CO2 NH4CNO 
 heat 

 NH2 .CO.NH2
ammonium cyanate Urea
is called dry ice.
Carbon exhibits unique properties like catenation Preparation of other organic
and isomerism. Petroleum, coal, wood and natural compounds :
gas are the main sources of carbon compounds. This reaction gave a big blow to the vital force
Distillation of petroleum gives variety of carbon theory. In 1844, Kolbe prepared acetic acid from
compounds. Dry distillation of coal gives many its elements and in 1856, Berthelot synthesized
important carbon compounds. methane and the most abundant organic
compound cellulose, which is a polymer of glucose.
3. Vital Force Theory Thus, the vital force theory was rejected, and it
The complex nature of organic compounds and was recognised that all chemical compounds
whether organic or inorganic, have the same
the observations mentioned above led to the
chemical forces operating in them. Kekule and
common belief that the organic compounds were
Couper proposed the tetravalency of carbon and
produced under the influence of some natural
wrote the first structural formula. In 1874,
forces called vital forces. This led to the vital force Vant’hoff and Le Bell suggested a tetrahedron
theory for the formation of organic compounds in model of carbon atom.
plants and animals. Berzelius was one of the strong
supporter to this theory.
Organic Chemistry 385
Modern definition of organic 4. Reasons for the formation of
chemistry large number of compounds
Since the synthesis of urea from ammonium All organic compounds contain carbon as an
thiocyanate, many organic compounds were essential element. In addition to it, there can be
prepared and analysed. Presently about five million hydrogen and oxygen atoms. In more complex
organic compounds are known. It was recognised organic compounds, there can be sulphur, nitrogen,
chlorine, bromine, iodine, phosphorus atoms in
that the chemical forces in organic compounds are addition of carbon, hydrogen and oxygen atoms.
similar to those which exist in the inorganic Tetravalency of carbon :
compounds. According to the modern definition, Carbon atom has four electrons in its valence shell.
organic chemistry is “that branch of chemistry Thus, in order to satisfy its valence shell, it shares
which deals with the study of compounds of carbon its electrons with neighbouring carbon atoms or
with the atoms of other elements.
with hydrogen (hydrocarbons), and their
Carbon atom due to its tetravalency can be bonded
derivatives”. to two, three or four carbon atoms by forming
single and multiple bonds. Therefore, chains of
carbon atoms, may be linear, branched or cyclic.
For example,
(linear chain) (branched chain) (Cyclic)

(cyclic)
Carbon forms a number of compounds due C –– C 348

to : C –– O 315
(i) Catenation : The unique property of C –– H 414
carbon atoms to link with other carbon C –– Cl 326
atoms to form long straight or branched C –– F 439
carbon chains of any length or closed rings (ii) The ability to form double and triple
of any complexity is called bonds : The first ionisation energy (now
catenation. It is the property of catenation ionisation enthalpy)of carbon atom is 1085
which is responsible for the formation of KJ/mol. This value is very high. The electro
very large number of organic compounds. negativity of carbon is 2.5,
Catenation is favoured by the atoms where which is neither too low nor too high. Thus,
atom to atom covalent bond is quite strong. carbon has no tendency to lose or gain
In carbon, C –– C bond enthalpy is very electrons. As a result, it forms bonds only
large (347.3 KJ mol–l). So, carbon shows by mutual sharing of electrons and thus
catenation. The reason for forms only covalent bonds.
greater tendency of carbon for catenation Carbon forms p   p  multiple bonds with
than other elements in the group is due to itself and with other elements, particularly
the C –– C bond energy is approximately nitrogen and oxygen. As a result, a large
of the same magnitude as the energies of number of compounds
the bond between C and other elements.
Bond B.E (kJ/mol)
H H O
C=C H C C H CH3 C CH3 C N
H H OH
ethylene acetylene acetic acid methyl cyanide
(ethene) (ethyne) (ethanoic acid) (ethanenitrile)
8. Statement I: The carbon present in organic

F ormative W orksheet compounds is always quadri- covalent in nature.
Statement II:Organic compounds are volatile in
1. The compounds of carbon other than carbon nature.
monoxide, carbon dioxide, and carbonates are 1) Statement-1, Statement-2 both are true and
called : Statement-2 is the correct explanation of
1) Organic compounds Statement-1.
2) Chemical compounds 2) Statement-1, Statement-2 both are true but
3) Both 1 and 2 Statement-2 is not the correct explanation of
Statement1.
4) Physical compounds
3) Statement-1 is true, Statement-2 is false.
2. Column-I Column-II 4) Statement-1 is false, Statement-2 is true.
a) Lavoisier 1) Prepared acetic acid
b) Kekule 2)Synthesized methane
c) Berthelot 3) Father of modern
C onceptive Worksheet
chemistry 1. The branch of chemistry dealing with carbon
d) Kolbe 4) Tetravalency of compounds is
carbon 1) Nuclear chemistry 2) Organic chemistry
5) Tetravalency of
3) Physical chemistry 4) Inorganic chemistry
phosphorous
2. Who found that organic compounds contains
3. In addition to carbon, the following atoms can be
carbon, hydrogen, oxygen and nitrogen ?
present in organic compounds:
1) Platinum, Radium, Nitrogen, Neon 1) C. W. Scheele 2) Lavoisier
2) Silver, Thorium, Argon 3) Berthlot 4) F. Wohler
3) Chlorine, Uranium, Radon, Gold 3. According to modern definition, organic chemistry
4) Sulphur, Nitrogen, Phosphorus, Chlorine deals with
4. Which of the following statement is right? 1) Chemistry of hydro carbons
1) Organic compound cannot be synthesised in 2) Derivatives of hydro carbons
laboratory 3) Chemistry of carbon monoxide , carbondioxide
2) Organic compounds have low melting and 4) None
boiling points 4. Statement I: The catenation ability is maximum in
3) Organic compounds show isomerism carbon
4) Organic compounds show molecular reactions Statement II: The C-C bond energy is
5. Tetrahedron model of carbon atom was given by approximately of the same magnitude as the
1) Kekule 2) Lewis energies of the bond between C and other
3) Koble 4) Van’t Hoff and Le-Bel elements.
6. Which of the following are inorganic compounds? 1) Both Statements are true, Statement II is the
1) Ammonium cyanate 2) Potassium cyanate correct explanation of Statement I.
3) Urea 4) None of these 2) Both Statements are true, Statement II is not
7. The first organic compound synthesised in the correct explanation of Statement I.
laboratory from its elements is 3) Statement I is true, Statement II is false.
1) Urea 2) Methane 4) Statement I is false, Statement II is true.
3) Ethylene 4) Acetic acid
5. Organic chemistry deals with the study of: Example, X-M-X

1) The compounds obtained from plants only sp
2) The compounds obtained from animals only (M=Be,Zn,Hg)
3) The compounds obtained from minerals HC  CH
4) The compounds of carbon sp sp
6. Essential constituent of all organic compounds is: Some other examples are CO2,CS2 BeCl2,ZnCl2
1) Nitrogen 2) Sulphur etc.
3) Carbon 4) Hydrogen Characteristics of sp-Hybrid
7. Which one of following is not an organic
Orbitals
compound?
(i) Shape of sp-hybrid orbitals is oval.
1) Ammonium cyanate 2) Marsh gas
(ii) Its relative power of overlapping is 1.93
3) Urea 4) Cane sugar
with respect to s orbital.
8. Column-I Column-II
(iii) Both sp-hybrid orbitals are completely
a) Lime stone 1) CaCO3.MgCO3
equivalent and symmetrical.
b) Magnesite 2) ZnCO3
(iv) These two sp-hybrid orbitals are collinear,
c) Dolomite 3) CaCO3
i.e., angle between the hybrid orbitals is
d) Calamine 4) MgCO3
180º.]
5) CdCO3
(v) Energy of sp-hybrid orbital is more than s-
orbital but less than the p-orbital.
5. Hybridization In sp-hybrid orbital, one lobe is bigger while
Pauling and Slater introduced it to explain the other lobe is small. The bigger lobe is very
shape of molecules which can be explained by large with respect to p-orbital, hence it has
VBT. It is the intermixing or re-distribution of higher degree of overlapping. So it forms
energy among two or more half filled or full filled stronger bond. For example, in the
or incomplete or empty orbitals of comparable formation of acetylene.
energy to form same number of hybrids. Hybrids In acetylene, hybridization of carbon is sp.
have identical energies and similar shapes. One 2s orbital blends with only 2p
Facts about Hybridization orbital to form two sp-hybrid orbitals. In
1. Number of atomic orbitals taking part in this case, two unhybridized orbitals remain,
hybridization is equal to number of hybrids formed. each with ne electron.
2. Electrons do not undergo hybridization 2. sp2 hybridization:
3. A hybrid bond is always a sigma bond Here one s and two p orbital intermix to form
4. A hybrid bond is always stronger than a non-hybrid three new sp2-hybrids. Shape of the species is
bond. trigonal or co-planar and bond angle is 120º
5. Hybridization occurs at the time of bond formation.
6. Hybridization  overlapping (for enough over Characteristics of sp2-Hybrid Orbitals
lapping orbitals must be fairly apart that is, neither (i) These hybrid orbitals are planar with bond
very close nor very far.) angle 120º.
7. Hybridization is for increasing stability and (ii) These sp2-hybrid orbitals are completely
decreasing reactivity and energy. equivalent and symmetrical.
8. Hybridization is of central atom in a molecule (iii) These are stronger than s and p orbitals.
(NH3,H 2O,CH4). Its relative power of overlapping is 1.99
8. Hybridization is not meant for isolated atoms but with respect to s-orbital.
for bonded atoms. (iv) As in this hybridization contribution of p-
orbitals is more hence it is less oval than
Types of Hybridizations
sp-hybrid orbitals. In this case, one lobe is
1. sp hybridization bigger and one lobe is smaller and its forms
Here one s and one p orbital form two sp hybrids stronger bond.
after intermixing. Shape of molecule is linear and When carbon is bonded to another atom
bond angle is 180º by a double bond, the carbon atom is in the
sp2-hybrid state. Example is ethylene.
In order to form sp2 bonding orbitals, carbon
 In sigma bond free rotation is possbile.
hybridizes its 2s orbitals with only two of its
orbitals. One p-orbital remains unhybridised on  Sigma bond determines the shape of molecule.
the carbon atom, In ethylene two sp2 carbons are Pie    Bond
joined by a sigma bond formed due to the overlap
 It is formed by lateral or sidewise overlapping
of one sp2 orbitals from each carbon atom.
between two p orbitals.
Both carbon atoms also have unhybridized p-
orbitals, which can be oriented parallel to each  It is a weak or less stable bond but more reactive
other and therby overlap. Both lobes of the p- due to less effective overlapping.
orbitals merge above and below the sigma bond  Minimum and maximum number of pi bonds
formaing a  MO. Thus double cond is composed between two bonded atom is 0 and 2
of a  and a  bond. The ethylene molecules respectively.
are completed when  bonds are formed between  Stability  1/number of pi bonds.
the overlapping sp2 orbitals of carbon and the s-  Reactivity  number of pi-bonds
orbitals of the hydrogens.
3. sp3 hybridization:
Here one s and three p orbitals intermix to give
F ormative Worksheet
four new sp3 hybrids. Shape of the species is 9. In which of the following compounds, the
tetrahedral and bond angle is 109º28. underlined carbon as sp3-hybridization?
Example,
1) CH3  CH  CH2 2) CH3 CO NH2
C6H6 ,CX 4 ,SiX 4 ,NH4 ,PH3 ,H2O,H2S ,
3)  CH3 3 C  CH2

Characteristics of sp3-Hybrid 4) CH3COOH
Orbitals 10. How many sigma and pi bonds are there in the
(i) These orbitals are directed towards the four molecule of dicyanoethene
corners of a regular tetrahedron and the (CN-CH=CH-CN)?
angle between each pair of them is 109º28 1) 3 sigma and 3 pi 2) 5 sigma and 2 pi
or 109.5º 3) 7 sigma and 5 pi 4) 2 sigma and 3 pi
(ii) All the four sp 3 hybrid orbitals are 11. Which of the following compounds have only sp3
completely equivalent and symmetrical. hybridization carbon(s)?
(iii) As in sp3 hybridization the contribution of 1) Ethane 2) Methane
p-orbitals is 75 percent, its shape is almost 3) Ethyne 4) Propane
same as that of the parent p-orbitals except 12. The hybridization present in C2H2 is
that the bigger lobe in sp 3-orbitals is 1) sp 2) sp2 3) sp3 4) dsp2
somewhat more spread and shorter in 13. Statement I: Hybridization is for increasing
length than the pure p-orbitals stability and decreasing reactivity and energy.
Their relative power of overlapping is 2.00 Statement II: A hybrid bond is less stronger than a
with respect to s-orbitals. This shows that non hybrid bond.
sp3-orbitals are stronger than sp2 which is 1) Both Statements are true, Statement II is the
stronger than sp-orbitals. correct explanation of Statement I.
Sigma bond 2) Both Statements are true, Statement II is not
 It is formed by axial or head to head or linear correct explanation of Statement I.
overlapping between two s-p or p-p orbitals. 3) Statement I is true, Statement II is false.
4) Statement I is false, Statement II is true.
 Sigma bond is stronger but less reactive due to
14. Which of the following has all carbon atoms of
more effective and stronger over lapping than the
sp-hybridized?
pi bond.
 The minimum and maximum number of sigma bond 1) CH3  CH  CH  CH3
is between two bonded atom is one. 2) HC  C  C  CH
 Stability  number of sigma bonds. 3) CH3  C  C  CH3
 Reactivity  1/  4) All of the above
15. As the s- character increases , electronegativity 1) Both Statements are true, Statement II is the
1) Increases 2) Decreases correct explanation of Statement I.
3) Remains same 4) All of these 2) Both Statements are true, Statement II is not
correct explanation of Statement I.
16. Among the sp,sp2 ,sp3 hybrid orbitals , which
3) Statement I is true, Statement II is false.
is more electronegative ? 4) Statement I is false, Statement II is true.
1) sp 2) sp 2 13. The hybridization of carbon in benzene is:
3) sp 3 4) Both A & B 1) sp3 2) sp 3) sp2 4) dsp2
14. In ethyne, the number of sigma and pi bonds are:
17. What is the % of ‘s’ character in sp hybridisation
1) 75 % 2) 25 %
1) Two sigma and three pi
3) 33.3 % 4) 50 %
2) Three sigma and two pi
18. The orbitals used by the carbon in the formation
3) Two sigma and one pi
of C2H4Cl2 molecule are
4) One sigma and two pi
1) Four sp3 2) Four sp2
15. In which of the compounds below is there more
3) Four sp 4) None of these
than one kind of hybridization (sp,sp2,sp3) for
19. The statement which are true among the following
carbon?
is
1) The hybrid orbitals have a different shape from 1) CH3 CH2CH2CH3
the orbitals from which they have been hybridized. 2) CH3  CH  CH  CH3
2) The  bond is stronger than a  bond as there
3) CH2  CH  CH  CH2
are two regions of electron cloud , one above
and one below the line joining the nuclei 4) H  C  C  H
3)  bond orbitals can be formed by the linear 16. Column-I Column-II
overlap of s - and p- orbitals, p- and p- orbitals. a) Linear overlapping 1) Ethylene
4) Formation of covalent bonds by the overlap of b) Side wise overlapping also
orbitals is accompanied by the release of energy. called as 2) Sigma bond
c) 5 sigma bonds, 1 pi bond 3) Ethane
d) Only sigma bonds present 4) Methane
C onceptive Worksheet 5) Lateral overlapping
9. In benzene molecule there are 3pi bonds and
1) 3 sigma bonds 2) 6 sigma bonds CLASSIFICATION OF ORGANIC
3) 10 sigma bonds 4) 12 sigma bonds COMPOUNDS
10. Which of the following possesses a sp-carbon in
6. Classification of organic
its structure?
compounds based on structure
1) CH2  CCl  CH  CH2
The simplest organic compounds containing only
2) CCl2  CCl2 carbons and hydrogens are called hydrocarbons.
Other organic compounds are thought to have been
3) CH2  CH  CH  CH2 derivative of hydrocarbons. All the known organic
4) CH2  C  CH2 compounds have been broadly divided into two
categories depending upon the nature of their
11. Which of the following is/are correct?
carbon skeleton.
1) The sp2 hybrid orbitals are planar
(1) Open-chain or Acyclic compounds.
2) Shape of sp hybrid orbitals is oval
(2) Closed-chain or Cyclic compounds.
3) Both sp hybrid orbitals are completely
equivalent and symmetrical (1) Open-chain or Acyclic compounds :
4) None of these These are the compounds in which the carbon
12. Statement I: Stability is proportional to number atoms are linked to each other in such a manner
of sigma bonds that the molecule is having an open-chain
Statement II: The minimum and maximum structure. The carbon chain may be either straight
number of sigma bonds between two bonded chain or branched-chain. Such compounds are
atoms is 1 known as aliphatic compounds.
Examples are :
(2) Closed-chain or Cyclic compounds :

Compounds containing atleast one ring in their structure are called cyclic compounds. If the ring contains
one type of atoms, the compound is homocyclic, and if the ring contains atleast one hetero atom, the compound
is called heterocyclic. Depending upon the nature of the ring, these compounds are further divided into the
following two categories :
(A) Homocyclic or Carbocyclic compounds : When all the atoms of the ring are carbons, the cyclic
compounds are known as homocyclic compounds. For example,
Homocyclic compounds are further divided into two categories :

(i) Alicyclic homocyclic compounds : Homocyclic compounds which resemble aliphatic compounds
are called alicyclic compounds. Some of the examples are :
(ii) Aromatic compounds : Compounds containing one or more fused or isolated benzene rings (a
six membered ring of carbon atoms with alternate single and double bonds) are called aromatic
compounds.
Examples :
(B) Heterocyclic compounds : Cyclic compounds having at least one heteroatom (atom other than
carbon) in the ring are heterocyclic compounds. Heterocyclic compounds can be classified into two categories
:
(i) Alicyclic heterocyclic compounds : Heterocyclic compounds which resemble aliphatic compounds
in their properties are called alicyclic heterocyclic compounds.
(ii) Aromatic heterocyclic compounds : Heterocyclic compounds which resemble aromatic

compounds in most of their properties are called aromatic heterocyclic compounds.
The classification may be summarised as follows :

Organic compounds
Open – chain Closed – chain

or or
Acyclic Cyclic
Homocyclic Heterocyclic
Alicyclic Aromatic Alicyclic Aromatic
Benzenoid Non-Benzenoid
7. Classification of organic compounds based on type of bond present

Hydrocarbons
A compound made up of hydrogen and carbon only is called hydrocarbon.
(Hydrogen + Carbon = Hydrocarbon).
Example : Methane(CH4), Ethane(C2H6), Ethene(C2H4), and Ethyne (C2H2).
The most important natural source of hydrocarbons is petroleum which is obtained from underground oil
deposits by drilling oil wells.
Types of hydrocarbons
Hydrocarbons are of two types : (i) Saturated hydrocarbons
(ii) Unsaturated hydrocarbons.
(i) Saturated hydrocarbons : A hydrocarbon in which caron atoms are connected by only single
bonds is called a saturated hydrocarbon. Saturated hydrocarbons are also called alkanes.
Alkanes : An alkane is a hydrocarbon in which carbon atoms are connected by only single covalent
bonds. The names of all these saturated hydrocarbons end with ‘ane’.
Example : Methane(CH4), Ethane(C2H6), Propane(C3H8) etc.
The general formula of saturated hydrocarbons is CnH2n+2 where n is the number of carbon atoms
in one molecule of alkane.
(i) If an alkane has one carbon atom in its molecule, then n = 1 and its molecular formula will be
CH 4 .
(ii) If an alkane has two carbon atoms in its molecule, then n = 2 and its molecular formula will be
C2H 6.
Alkane Number of carbon atoms Formula (CnH 2n+2)

Methane 1 CH4
Ethane 2 C 2H6
Propane 3 C 3H8
Butane 4 C 4H1 0
Pentane 5 C 5H1 2
Hexane 6 C 6H1 4
Heptanes 7 C 7H1 6
Octane 8 C 8H1 8
Nonane 9 C 9H2 0
Decane 10 C 10H2 2
The saturated hydrocarbons are chemically not very reactive.
(ii) Unsaturated hydrocarbons : A hydrocarbon in which two carbon atoms are connected by a
double bond or a triple bond is called an unsaturated hydrocarbon. Alkenes and alkynes are called
unsaturated hydrocarbons.
Example : Ethene(C2H4), Propene(C3H6), Butene(C4H8)
Alkenes : An alkene is a hydrocarbon in which carbon atoms are connected by double bonds.
The names of alkenes end with ‘ene’.
The general formula of alkenes is CnH2n where n is the number of carbon atoms in one molecule
of alkane.
(i) If an alkene has two carbon atoms in its molecule, then n = 2 and its molecular formula will be
C2H 4.
(ii) If an alkane has three carbon atoms in its molecule, then n = 3 and its molecular formula will be
C3H 6.

Ethane 2 C2H4
Propane 3 C3H6
Butane 4 C4H8
Pentane 5 C5H1 0
Hexane 6 C6H1 2
Heptanes 7 C7H1 4
Octane 8 C8H1 6
Nonane 9 C9H1 8
Decane 10 C10H2 0
Alkynes : An unsaturated hydrocarbons in which the two carbon atoms are connected by a triple bond is
called an alkyne. The names of alkynes and with ‘yne’.
Example : Ethyne(C2HB), Propyne(C3HD), Butyne(C4H6) etc.
The general formula of alkynes is CnH2n–2 where n is the number of carbon atoms in one molecule of alkane.
(i) If an alkyne has two carbon atoms in its molecule, then n = 2 and its molecular formula will be
C2H 2.
(ii) If an alkane has three carbon atoms in its molecule, then n = 3 and its molecular formula will be
C3H 4.

Ethane 2 C2H2
Propane 3 C3H4
Butane 4 C4H6
Pentane 5 C5H8
Hexane 6 C6H1 0
Heptanes 7 C7H1 2
Octane 8 C8H1 4
Nonane 9 C9H1 6
Decane 10 C10H1 8
Alkyl group : By removing a hydrogen atom from an alkane, alkyl group is obtained.
Alkyl group is represented by R –.
While deriving the name of an alkyl group “ane” of alkane is replaced with “yl”. Thus
Alkane  H atom = Alkyl group
A unit called methylene group - CH2
The difference between carbon and hydrogen atoms in the first four members of alkanes is,
1. Difference between ethane and methane = [C2H6 - CH4] = CH2
2. Difference between propane and ethane = [C3H8 - C2H6] = CH2
3. Difference between butane and propane = [C4H10 - C3H8] = CH2
The difference of carbon and hydrogen atoms between two consecutive members of alkanes is CH 2. This
—CH2 unit is called methylene group.
By removing one or more CH2 groups from a given saturated hydrocarbon, we can obtain another saturated
hydrocarbon with lesser number of carbon atoms.
Similarly, by adding one or more CH2 groups in a given saturated hydrocarbon, we can obtain another
hydrocarbon with more number of carbon atoms.
Furthermore, there is a difference of 14 amu (molecular mass of CH2 is 14) between two consecutive
hydrocarbons.
8. Homologous series
Alkanes have a general formula Cn H2n + 2 and each member differs from the next by a fixed group — CH2
— (the methylene group), even they have similar chemical properties. In other classes of compounds like
alkenes, alkynes, alcohols or acids, the same thing happens. Such a series of compounds is known as a
homologous series and the individual members are homologues.
Compounds having the same functional group and similar properties that differ from the adjacent members
by a — CH2 — group constitute a homologous series and the phenomenon is called homology.
The members of the same class of organic compounds, when arranged in the order of ascending
molecular weights such that they differ from each other by – CH2 group, are collectively called
homologues.
Example of a homologous series for each class (or family) of compounds are :
Alkane Formula (Cn H2n+2) Difference in formulae
Methane CH 4 CH2
Ethane C2H 6 CH2
Propane C3H 8 CH2
Butane C4H 10 CH2
Pentane C5H 12

Ethane C2H 4 CH2
Propane C3H 6 CH2
Butane C4H 8 CH2
Pentane C5H 10

Ethane C2H 2 CH2
Propane C3H 4 CH2
Butane C4H 6 CH2
Pentane C5H 8
Alkane Formula (C nH2 n+2) Difference in formulae

Methanol CH 3OH CH 2
Ethanol C2 H5OH CH 2
Propanol C3 H7OH CH 2
Butanol C4 H9OH CH 2
Pentanol C5H 11OH
Characteristics of a homologous series

The members of a homologous series can be represented by a general formula, e.g., the alkanes by CnH2n+2,
alkenes by CnH2n, alkynes by CnH2n–2 and alcohols by CnH2n+1OH, where ‘n’ stands for number of carbon
atoms in one molecule of alkane.
Every member of a homologous series differs from the adjacent ones in composition by CH2.
This is because every succeeding member of a homologous series arises by the replacement of an H atom
in the preceding member by a CH3 group. For example, C2H6 (ethane) may be thought to arise from CH4
(methane) as follows.
The molecular masses of two consecutive members of a homologous series differ by 14 amu (equivalent to
one CH2 group).
Generally, similar methods may be employed to prepare all the compounds belonging to a homologous series.
The physical properties of the compounds of a homologous series change gradually as the molecular mass
changes. For example, the melting point, boiling point and density increase with molecular mass.
The chemical properties of the compounds belonging to the same homologous series are similar.
20. Which of the following is an aromatic compound?
1) Benzene 2) Naphthalene 3) Furan 4) All of these
21. Which of the following properties is not true regarding organic compounds?
1) They are generally covalent compounds 2) They have high melting and boiling points
3) They are generally insoluble in water 4) They usually show isomerism.
22. Statement I: In Homologous series two 19. Which of the following is/are correct statements?
successive members differ in their atomic mass 1) CH 2 unit is called methylene group
by 14 atomic units 2) The members of a homologues series can be
Statement II: Homologous series of structurally differ from each other in molecular formula by
similar compounds having same functional group
in increasing by one carbon and two hydrogen CH 2 unit
atoms. 3) Examples for alicyclic compounds are THF ,
1) Both Statements are true, Statement II is the cyclohexane etc
correct explanation of Statement I. 4) None of these
2) Both Statements are true, Statement II is not 20. Statement I: When all the atoms of the ring are
correct explanation of Statement I. carbons the cyclic compounds are known as
3) Statement I is true, Statement II is false. homocyclic compounds.
4) Statement I is false, Statement II is true. Statement II: A hydrocarbons in which carbon
23. An example of alicyclic compound is atoms are connected by only single bonds is called
1) Benzene 2) Hexane saturated hydrocarbon.
3) Cyclohexane 4) Both 1 and 3 1) Both Statements are true, Statement II is the
24. Which of the following is/are aromatic correct explanation of Statement I.
heterocyclic compound(s)? 2) Both Statements are true, Statement II is not
1) Quinoline 2) Pyridine correct explanation of Statement I.
3) Thiophene 4) None of these 3) Statement I is true, Statement II is false.
25. Which of the following is an aromatic compound? 4) Statement I is false, Statement II is true.
1) Benzene 2) Anthracene 21. Which one of the following statement is incorrect?
3) Naphthalne 4) All are aromatic 1) The members of a series have the general
26. Which one is correct for a homologus series? formula CnH2n+2 where ‘n’ is anpositive integer.
1) All members have a general formula. 2) The difference between any two successive
2) All members have similar chemical properties. members of the series corresponds to 14 unit of
3) All members have same physical properties. relative atomic mass.
4) All members have same functional group. 3) The members of the series are similar to each
27. Which of the following is not a carbocyclic other.
compound? 4) All the above
1) Cyclopentane 2) Naphthalene 22. Two members of the homologous series have
3) Thiophene 4) Benzene 1) Different molecular formula
28. Which one is/are correct statement? 2) Different general methods preparation
1) Open chain compounds are called aliphatic 3) Different chemical properties
compounds 4) Both 1 and 2
2) Unsaturated hydrocarbons contain double or 23. Which of the following includes the members of a
triple bond between carbon atoms homologous series?
3) Aromatic compounds possess a characteristic 1) HCOOH, CH3COOH, CH3CHO
aroma 2) CH3OH,C2H5OH, C3H7OH
4) None of these 3) CH3Cl, CH3CHO, OH
4) HCHO, CH3CHO, C2H5OH
17. Which of the following is an example of alicyclic
homocyclic compound?
1) Benzene 2) Pentane
3) Cyclo pentane 4) Furan
18. Which of the following are aromatic heterocyclic
compound?
1) Furan 2) Pyrole
3) Thiophene 4) All the above
a) Alicyclic compounds 1)
b) Aromatic compounds 2)
c) Hetero cyclic compounds 3)
d) Cyclo hexene 4)
5) Anthracene
9. State of carbon in carbon compounds

The ground state electronic configuration of carbon is 1s2 2s2 2p1x 2p1y 2p0z
The excited state electronic configuration of carbon is 1s2 2s1 2p1x 2p1y 2p1z
Energy of excitation is 120 k. cal mol–1 or 501.6 kJ mol–1.
Tetrahedral nature of carbon was proposed by Vant Hoff and Label.
In organic compounds carbon atom, undergoes sp, sp2 and sp3 hybridisations.
% character of Nature of bonds
Orbitals Bond Orientation of
Hybridisation orbitals around carbon
involved angles orbitals
s P atom
one s all 
sp3 25 75 109°28' Tetrahedral
three p no 
one s 3 
sp2 33.3 66.6 120° Trigonal planar
two p 1 
one s 2 
sp 50 2 180° Linear
one p 2 
sp3 hybridised carbon is called saturated carbon.
sp and sp2 hybridised carbons are called unsaturated carbons.
Greater the s - character, less is the orbital size, lower the energy.
The order of size of different orbitals is p > sp3 > sp2 > sp > s
Bond length in carbon compounds.
C – C bond length is 1.54 Å C = C bond length is 1.34 Å

C C bond length is 1.20 Å C – H average bond length is 1.1 Å
Bond energies :
Energy
Bond
k.cal mol-1
sp3 – s 104
sp2 - s 106
sp - s 121
3 3
sp – sp 80 - 90
sp2 - sp2 120 - 164
sp – sp 123 - 199
sp3 – sp3 < sp2 – sp2 < sp – sp

Hybrid orbitals :
i) overlap better
ii) provide greater bond angles there by minimise the repulsion between electron pairs.
Bonds formed by hybrid orbitals are more stable than the bonds formed by the pure atomic orbitals.
The C – H bond energy increases with increase in ‘s’ character sp3 - s < sp2 - s < sp - s.
29. Match the following :
Column - I Column - II Column - III
S) sp3 p) 2, 2 k) Trigonal planar
E) sp2 q) no , all  l) Tetrahedral
T) sp r) all , no  m) Linear
s) 3, 1 n) Octahedral
S E T
a) r, m s, n p, k
b) r, l s, k p, n
c) r, k s, l p, m
d) r, l s, k p, m
30. The carbon atoms are closest to each other in
a) H3C – CH3 b) H2C  CH2 c) HC  CH d) C – C in diamond
31. The compound in which C – C bond lengths are equal is :
a) H2C  CH  CH  CH2 b) HC  C  C  CH
c) CH3  CH2  CH2  CH3 d) All
25. s-character of sp,sp2 and sp3 hybrid orbitals follows the order
a) sp > sp2 > sp3 b) sp3 > sp2 > sp c) sp3 >sp > sp2 d) None
26. Which of the following order of decreasing energy is correct?
a) sp3  p  sp2  sp  s b) s  sp  sp2  sp3  p
c) p  sp3  sp2  sp  s d) s  sp3  sp2  sp  p
27. Select the strongest bond.
a) C C b) C=C c) C C d) C C
d) HCHO, CH3CHO, C2H5OH
10. Classification of organic compounds based on type of functional

group
Functional groups
A saturated hydrocarbon is unreactive but if we introduce some other ‘atom’ or ‘group of atoms’ into it, the
resulting compound becomes very reactive. This other ‘atom’ or ‘group of atoms’ present in a carbon
compound is known as a functional group. Thus, an ‘atom’ or ‘a group of atoms’ which makes a carbon
compound (or organic compound) reactive and decides its properties (or functions) is called a
functional group.
different). The ketone group is sometimes called
1. Halo group : —X(X can be Cl, Br or I) a ketonic group. The compounds containing ketone
The halo group can be chloro, —Cl ; bromo, —Br group are known as ketones. The ketone group
; or iodo, —I, depending upon whether a chlorine, occurs in the middle of the carbon chain in between
bromine or iodine atom is linked to a carbon atom the two CH3 groups. A ketone group can never
of the organic compound. occur at the end of a carbon chain.
chloro group is present in chloromethane, Ex : Propanone (CH 3 COCH 3 ), Butanone
CH3—Cl, (CH3COCH 2CH3)
bromo group is present is bromomethane, 5. Carboxylic acid group :
CH3—Br, and
O
iodo group is present in iodomethane, CH3—I
COOH or C OH
2. Alcohol group : —OH
The alcohol group is made up of one oxygen atom Carboxylic acid group is present in methanoic acid,
and one hydrogen atom joined together. The alcohol H—COOH and ethanoic acid, CH3—COOH.
group is also known as alcoholic group or hydroxyl The carboxylic acid group is also called just
group. The compounds containing alcohol group carboxylic group or carboxyl group. The organic
are known as alcohols. compounds containing carboxylic acid group
(—COOH group) are called carboxylic acids or
Ex : Methanol (CH3OH), Ethanol (C2H5OH) organic acids.
3. Aldehyde group : — CHO or
O H 6. Alkene group : C C
C H or C O The alkene group is a carbon-carbon double bond.

The alkene group is present in ethene (CH2 =
The aldehyde group consists of one carbon atom, CH2), and propene (CH 3 – CH = CH2). The
one hydrogen atom and one oxygen atom joined compounds containing alkene group are known
together. Please note that though the oxygen atom as alkenes.
of the aldehyde group is attached to the carbon
7. Alkyne group : C C
atom but for the sake of convenience in writing,
the aldehyde group is written as —CHO (with The alkyne group is a carbon-carbon triple bond.
hydrogen atom in-between the carbon and oxygen The alkyne group is present in ethyne
atoms). The carbon atom of the aldehyde group is
 CH  CH  and propyne  CH3  C  CH  .
attached to either a hydrogen atom or an alkyl
group. The compounds containing alkyne group are
known as alkynes.
Ex : Methanal (HCHO), Ethanal (CH3CHO),
Propanal (CH3CH2CHO) All organic compounds having same functional
group show similar chemical properties.
4. Ketone group :
O
C O or C or CO
The ketone group consists of one carbon atom and

one oxygen atom. The oxygen atom of the ketone
group is joined to the carbon atom by a double
bond.
The carbon atom of the ketone group is attached
to two alkyl groups (which may be same or
Table representing functional groups of organic compounds.
Functional Name of the
S.No Name Formula
group functional group
1. Alkanes R–H – –
Alkenes C=C Double bond
2. R – CH = CH2
3. Alkynes R  C  CH C  C  Triple bond
4. Alkyl halides RX X Halogen
5. Alcohols (Alkanol) R  OH  OH Hydroxyl
Ethers Alkoxy
6. R  OR' O  R '
(Alkoxy alkane)
7. Aldehydes (Alkanal) R  CHO  CHO Aldehyde
8. Ketones (Alkanone) R  CO  R' C=O Keto
Carboxylic acids  COOH Carboxyl

9. R  COOH
(Alkanoic acid)
Esters  COOR' Ester
10. R  COOR '
(Alkyl alkanoates)
11. Amines (Alkanamine) R  NH2 NH2 Amino
12. Amides (Alkanamide) R  CONH2  CONH2 Amide
Cyanides Cyanide
13. RCN CN
(Alkane nitrile)
14. Nitro compounds R  NO2  NO2 Nitro
15. Acid halides R  COX  COX Acid halides
Functional Name of the
S.No Name Formula
group functional group
Acid anhydride (Alkanoic Acid anhydride
16. R  CO2 O   CO2 O
anhydride)
Acyl chloride (Alkanoyl O O Acyl chloride
17. || ||
chloride) R  C  Cl  C  Cl
Alkyl isocyanide (Alkyl Isocyanide
18. RNC N  C
carbyl amine)
32. Write the formula of the functional group present in the following compounds ?
a) Alkene b) Alkyne c) Alcohol d) Carboxylic acid
e) Aldehydes f) Ketones g) Esters
33. Write the name of the family represented by the following functional groups.
a) O  R ' b) NH2 c) CONH2
X
|
d) C  N e)  C  O
34. Name the functional groups present in
O
||
i) CH3COOH ii) CH3CH2CHO iii) C2H5OH iv) CH3 C CH2 CH3
35. Name one functional group which always occur in the middle of the carbon chain.
36. i) The atom or a group of atoms which makes a organic compound reactive and decides its properties
is called a ________.
ii) All organic compounds having same functional group show similar ________
There are mainly three types of naming.
They are i) Trivial naming, ii) Derived
C onceptive Worksheet naming and iii) Systematic naming.
28. Which of the following is an example of alicyclic Trivial names are also called common names.
homocyclic compound? In this system the compound is named after the
a) Benzene b) Pentane source from which it is obtained. For instance citric
c) Cyclo pentane d) Furan acid (obtained from citrus plant), uric acid
29. Which of the following are aromatic heterocyclic (obtained from urine), formic acid (obtained from
compound? red ants, formica means ants in Latin) etc.
a) Furan b) Pyrrole Derived names are based on the recognition of
c) Thiophene d) All the above certain familiar common names. Thus CH3.OH
30. Which of the following is/are alicylic heterocyclic is called carbinol and CH3.CH2.OH is called
compound? methylcarbinol.
a) Pyrrole b) Pyrrolidine Systematic naming of organic compounds was
c) Benzene d) Butane devised in 1892 in Geneva (Switzerland). This
31. Which of the following is not a carbocyclic system is also known as Geneva system or I.C.C.
compound? (International Chemical Congress). This was
a) Cyclopentane b) Benzene modified and adopted throughout the world and
c) Napthalene d) Thiophene popularly known as IUPAC ( International Union
32. An example of an acyclic compound is : of Pure and Applied Chemistry) nomenclature.
According to this system, certain rules have been
a) Benzene b) n-pentane evolved which enable to translate a structure into
c) Cyclobutane d) Pyrrole a name and vice versa. The nomenclature is
33. Which of the following contains fused benzene always undergoing modifications and revisions.
rings? The latest rules which are widely accepted were
a) Napthalene b) Anthracene given.
c) Both a and b d) None In the IUPAC system the name of the organic
34. Which of the following is an aromatic compound? compound consists of root word, primary suffix,
secondary suffix and prefixes.
a) Benzene b) Naphthalene i) Root word : This is the basic unit of the
c) Furan d) All of these name. The root word gets its name from the
number of carbon atoms present in the
longest carbon chain (parent chain). Chains
11. Nomenclature containing carbon atoms up to 4 have
Naming of organic compounds is an important special word roots based on the common names.
aspect in the study of organic chemistry. Since Chain containing more carbon
some millions of compounds are present, atoms get the root word from the Greek number
remembering their names is an herculean task. roots.
Carbon chain Word root Carbon chain Word root

C1 Meth C7 Hept
C2 Eth C8 Oct
C3 Prop C9 Non
C4 But C10 Dec
C5 Pent General Alk
C6 Hex
ii) Suffix :
a) Primary suffix : Suffix indicates the functional group. Primary suffix is added after the
root word to indicate the nature of the carbon - carbon bond.
Nature of the bond Pr imary suffix General name
Saturated C–C – ane Alkane
Unsaturated C = C – ene Alkene
Unsaturated C  C – yne Alkyne
b) Secondary suffix : A secondary suffix is added after the primary suffix to indicate the
nature of the functional group. Usually the terminal ‘e’ of the primary suffix is dropped
before adding the secondary suffix.
Functional group Sec.suffix Examples

Alcohols (–OH) – ol Ethane – ethanol (C2 H5OH)
Aldehyde (–CHO) – al Ethane – ethanol (CH 2CHO)
Ketone ( CO) – one Propane – propanone (CH 3COCH3)
Carboxylic acid (–COOH) – oic acid Propane – Propanoic acid (C2H 5COOH)
Ester (–COOR) – oate Ethane – ethanoate (CH3COOR)
Cyanide (–CN) – nitrile Ethane – Ethyl nitrile (C2H5CN)
– Isonitrile
Isocyanide (–NC) or Ethane – Ethylisonitrile (C 2H5NC)
Carbylamine
Acid chloride (–COCl) – oyl chloride Ethane – Ethanoyl chloride (CH3COCl)
Acid amide (–CONH2) – amide Ethane – Ethanamide (C2H 5CONH 2)
iii) Prefix : Prefixes are used to indicate (i) the cyclic nature of the compound and (ii) the nature of
substituent present on the parent chain. Thus like suffixes, prefixes are of two types namely
primary and secondary.
a) Primary prefix : The primary prefix cyclo is added before the root word to indicate the
cyclic nature of the carbon skeleton, e.g.
CH2
H 2C CH2 Pr imary Root word Pr im. suffix Sec. suffix IUPAC name
Cyclo pent pent  Cyclopen tan e
H 2C CH2
In case the compound is acyclic (open chain), no prefix is used.
(b) Secondary prefix : The group which are not considered as functional groups, in IUPAC
system of nomenclature, but regarded as substituents are called secondary prefixes. These
are added before the root word in case of acyclic compounds and before the primary suffix
in case of cyclic compounds. Some important secondary prefixes along with their groups
are.
Substituent Secondary prefix Substituent Secondary prefix

–F Fluoro  Diazo
N  N
– Cl Chloro – OR Alkoxy
– Br Bromo – CH3 (– Me) Methyl
–I Iodo C2H5  Et Ethyl
– NO2 Nitro CH2CH2CH3   Pr  n-Propyl
– NO Nitroso NO t-Butyl
To sum up, IUPAC name of an organic compound consists of following arrangement of root word, suffixes
and prefixes
Secondary prefix + Primary prefix + Root word + Primary suffix + Secondary suffix
Alkanes : These are saturated hydrocarbons with C –– C. The suffix of this class of compound is ‘ane’.
Thus, the systematic name of this class of compounds is Alk  ane  Alkane .
Alkanes have general formula CnH2n+2. The homologous series of alkanes is :
Formula Cn (H2n+2) IUPAC name

CH4 Methane
C2H6 Ethane
C3H8 Propane
C4H10 Butane
C5H12 Pentane
Alkyl group : By removing a hydrogen atom from an alkane, alkyl group is obtained. Alkyl group is represented
by R –.
While deriving the name of an alkyl group “ane” of alkane is replaced with “yl”. Thus
Alkane  H atom = Alkyl group
Names of Alkyl groups
Formula of IUPAC name Formula of

Alkane IUPAC name
(Trivial names) Alkyl radical
CH 4 Methane CH3 Methyl
C 2H 6 Ethane C2H5 Ethyl
C 3H 8 Propane C3H7 Propyl
C4H 10 Butane C4H9 Butyl
Classification of carbon and hydrogen in an organic compound

Carbon and hydrogen atoms of an organic ompound may be classified as :
1) First classification : First classification depends on the mode of arrangment of carbon atoms in the chain.
According to this classification we get four types of carbon atoms and three types of hydrogen atoms.
i) Primary carbon or 1°C : A carbon atom attached to one (or no) other carbon atom is called a
primary carbon.
ii) Secondary carbon or 2°C : If in a carbon chain a carbon is bonded to two other carbon atoms,
then it is known as secondary carbon.
iii) Tertiary carbon or 3°C : If in a carbon chain a carbon is bonded to three other carbon atoms,
then it is known as tertiary carbon.
iv) Quaternary carbon or 4°C : If in a carbon chain a carbon is bonded to four other carbon atoms,
then it is known as quaternary carbon.
The hydrogen atoms present on primary, secondary and tertiary carbon atoms are said to be primt
secondary and tertiary hydrogen atoms respectively. Quaternary carbon has no hydrogen.
(2) Second Classification : In this method the relative positions of different carbon atoms in a molecule are
designated with respect to the functional group it contains. These designations are done by small letters of
Greek alphabet. The carbon atom directly attached to the functional group is designated as   C, the
carbon atom next to it is indicated as  -carbon atom and the next to   C is  -carbon atom and so on.
Each of the hydrogens is given the similar , ,  and  designation as the carbon atom to which it is
attached.
For example :
Types of alkyl groups

a) Primary alkyl group : When one hydrogen atom is removed from the hydrogens attached to the
terminal carbon atom of an alkane, primary alkyl group is formed.
H
e.g.: CH3  CH2  CH3   CH3  CH2  CH2
Propane Primary propyl group
b) Secondary alkyl group : When an hydrogen atom is removed from the hydrogens attached to a
middle carbon atom which is linked on either side to carbon atoms, secondary alkyl group is
formed.
H
e.g.: CH3  CH2  CH3   CH3  CH  CH3
Propane Primary propyl group
 or isopropyl group 
c) Tertiary alkyl group : When the hydrogen atom attached to a carbon atom which in turn is
attached to three other carbon atoms is removed, tertiary alkyl group is formed.
d) I soalkyl gr oup : An alkyl group containing one terminal CH2– group and CH3  CH  group on
|
CH3
the other end with no other branching is said to be an isoalkyl group.

Eg : CH3  CH  CH2  , CH3  CH  CH2  CH2 
| |
CH3 CH3
isobutyl isopentyl
CH3
|
e) Neoalkyl group : A neo alkyl group contains one CH2 – group on one end and one CH3  C 
|
CH3
group on other end with no other branching in the chain.
CH3 CH3
| |
Eg : CH3  C  CH2  , CH3  C  CH2  CH2 
| |
CH3 CH3
neopentyl neohexyl
S.No Alkyl group Common name IUPAC name

n – propyl or
1. CH 3 – CH2 – CH2 – Propyl
primary propyl
CH 3
Isopropyl or
2. CH 1-Methylethyl
secondary propyl
CH 3
n – butyl or
3. CH3.CH2. CH 2 . CH2 . Butyl
primary butyl
CH3 .CH 2. CH –
4. sec – butyl 1 – Methylpropyl
CH 3
CH 3
5. CH3 C tert-butyl 1,1-Dimethylethyl
CH 3
The IUPAC system of nomenclature has retained some of the common names for branched alkyl groups
such as isobutyl, sec-butyl, tert - butyl etc.
37. Match the following
Column - I Column - II
P) Citricacid k) Methyl carbinol
A) CH 3.OH l) Red ants
R) Formic acid m) Urine
I) CH 3CH 2.OH n) Citrus plants
S) Uric acid o) Carbinol
P A R I S
a) k l m n o
b) m n o k r
c) n o l k m
d) n m l k o
38. (i) Carbon chain containing 4 carbon atoms has the word root _______.
(ii) Carbon chain containing 8 carbon atoms has the word root _______.
(i) (ii)
a) Prop Dec
b) But Non
c) Pent Oct
d) But Oct
Name Attached to
R) 1° Carbon p) Neo carbon k) 4 carbon atoms
O) 2° Carbon q) Primary carbon l) 3 carbon atoms
M) 3° Carbon r) Secondary carbon m) 2 carbon atoms
E) 4° Carbon s) Tertiary carbon n) 1 carbon atom
R O M E
a) q, n r, m s, k p, l
b) q, n r, m s, l p, k
c) q, m r, l s, k p, n
d) q, l r, n s, k p, m
40. In the structure :
CH3
H3C CH CH2 C CH3
CH3 CH3
The type of carbons present are :

a) One primary, two secondary, and one testiary.
b) Four primary, two tertiary, and one secondary.
c) One primary, one secondary, one tertiary and one quarternary.
d) Five primary, one secondary, one tetiary and one quarternary.
Column - I Column - II
C) Primary alkyl group k) CH3 CH CH2
CH3
CH3
H) Secondary alkyl group l) H 3C C CH2
CH3
I) Tertiary alkyl group m) CH 3 CH 2 CH 2
CH3
N) Isoalkyl group n) CH3 C CH3
A) Neo alkyl group o) CH3 CH CH3

C H I N A
a) m o n k l
b) k l m n o
c) m n o k l
d) l m k n o
42. The substituent group for prefixes Amino, Bromo, Methyl, Nitro are respectively,

a) CH3 ,  NH2 ,  Br,  NO2 b)  N  N,  CH ,  Br,  NH
3 2
c) NH2 ,  Br,  CH3 ,  NO2 d) NH2  Cl ,  NO2 ,  CH3
Statement B : When hydrogen atom is removed

C onceptive Worksheet from the hydrogens attatched to a middle carbon
atom which is linked to two other carbon atoms,
35. IUPAC means, tertiary alkyl group is formed.
a) International union of pure and application a) ‘A’ is true, ‘B’ is false.
chemistry. b) ‘A’ is false, ‘B’ is true.
b) International union of pure and applied c) Both ‘A’ and ‘B’ are true.
chemistry. d) Both ‘A’ and ‘B’ are false.
c) International union of pure and amendment 41. Assertion (A) : Suffix indicates the functional
chemistry. group.
d) International union of pure and amendment Reasson (R) : A secondary suffix is added
chemistry. to the primary suffix to indicate the nature of
.36. Which one is the correct statement? functional group.
a) IUPAC names are based on the structure of a) Both assertion and reason are correct and
compounds. reason is the correct explanation of assertion.
b) Common names are based on the structure of b) Both assertion and reason are correct but
compounds. reason is not the correct explanation of assertion.
c) Derived names are based on the structure of c) Assertion is correct and reason is incorrect.
compounds. d) Assertion is incorrect and reason is correct.
d) None of the above
37. The suffix for alchohols, aldehydes and ketones
Alkenes: These are unsaturated hydrocarbons
according to IUPAC are respectively:
with C = C. The suffix of this class of compounds
is “ene”. Thus, the systematic name of this class
a) – alc, – ald, – ket b) – ol, – al, – ket
of compounds is
c) – ol, – al, – one d) – alc, – ald, – one
38. Select the correct statement. Alk + ene = Alkene
Alkenes have the general molecular formula Cn
a) Prefixes are written before the name of the H2n. This homologous series is :
compound.
Formula Common name IUPAC name
b) The suffixes are written after the name of the
compound. CnH2n Olefin or Alkylene Alkene
c) The root word is the basic unit of the name.
C 2H4 Ethylene Ethene
d) All the above.
39. The structure remaining after one ‘H’ is removed C 3H6 Propylene Propene
from alkane is :
C 4H8 Butylene Butene
a) Alkyl group b) Aldehyde group
c) Alcohol group d) All of these Alkenyl group : The hydrocarbon residue
40. Statement A : When hydrogen atom is removed derived by removing a hydrogen atom from an
from the hydrogens attatched to the terminal alkene is called alkenyl group. Thus
carbon atom of an alkane, primary alkyl group is Alkene  H atom = Alkenyl group
formed.
Some of these alkenyl groups with their common names are :
CH2 = CH –
Vinyl Ethenyl
(C2 H3 –)
CH2 = CH – CH2 –
Allyl Propenyl
(C3H 5 –)
Alkynes : Hydrocarbons with C  C are called alkynes. The suffix of this class of compound is “yne”.
Thus, the systematic name of this class is
Alk + yne = Alkyne
Alkynes have the general molecular formula Cn H2n–2. This homologous series is :
Cn H 2n–2 Acetylenes Alkynes
C 2H2 Acetylene Ethyne
Methylacetylene or
C 3H4 Propyne
Allylene
C4 H6 Crotonylene Butyne
C 5H8 – Pentyne
Alkynyl group : The hydrocarbon residue derived from an alkyne by removing a hydrogen atom is called
alkynyl group.
Alkyne  H atom = Alkynyl group
Thus some of these alkynyl groups are :
CH  C  Acetylide Ethynyl
CH  C  CH2  Propargyl Propynyl
After learning about the names of simple hydrocarbons, let us consider the way of laming complex hydrocarbon
molecules. Since all the organic compounds are considered is derivatives of the alkanes, importance is to be
given for naming of these compounds first.
12. Basic Rules of Nomenclature

1. Longest chain rule : Select the longest possible continuous chain of carbon atoms which is called parent
chain and is named after that hydrocarbon.
Let us illustrate this by taking the following example :
1 2 3 4 5
6
CH3 . CH2 . CH2 . CH . CH . CH3
CH3 6CH2
7CH3
In this the longest chain consists of seven carbon Ethyl is cited before methyl inspite of its higher
atoms. Hence, the parent hydrocarbon is heptane location number.
but not hexane. 6. In case two or more groups are located in
2. Identify the substituent alkyl groups attached to equivalent positions in the carbon chain, the lower
the parent chain. number is assigned to that group which is written
In the above example, there are two methyl first in the name of the compound in the
groups attached to the parent carbon chain. alphabetical order.
3. Least sum rule : The parent carbon chain is then Example :
numbered in such a way that the carbon atoms C2H5
bearing the substituents get the lowest possible 9 8 7 6 5 4 3 2 1
CH3 CH2 CH CH2 CH2 CH2 CH CH2 CH3
numbers. 1 2 3 4 5 6 7 8 9
CH3
1 2 3 4 5
CH3 CH2 CH2 CH2 CH CH3 3 - Ethyl - 7 - methylnonane.
6CH2
7. When two chains of equal number of carbon atoms
compete for selection as the longest chain, select
7CH3 the one that has greater number of substituents
7 6 5 4 3 attached to it. The following example illustrates
CH3 CH2 CH2 CH C CH3 this point.
CH3 2CH2
CH3 CH3
1CH3 1 2 3 4 5 6 7
CH3 CH CH CH2 CH CH CH2
Out of these two possible ways, in the first way
the carbon atoms bearing the methyl groups were 2 CH2 CH3
given 4 and 5 and in the second way the numbers

1 CH3
given are 3 and 4. The second way gives least
sum (3 + 4 = 7), the second way of numbering is Two longest carbon chains are possible as shown.
correct. Obviously one chain has three substituents and
4. When the carbon chain carries two like the other one has four substituents. In both the
substituents, the number of location is repeated ways the longest chain has seven carbon atoms.
Thus the correct name of the compound is 3 -
using prefixes di - (2), tri - (3), tetra - (4) etc.
Ethyl - 2, 5, 6 - trimethyl heptane.
In the above compound, the methyl substituent is
8. If identical substituents are bonded to the same
present twice, hence the name is prefixed with di
carbon atom, then the position of the substituent
and their position is indicated with numbers. Thus, must be repeated.
the name of the compound is 3, 4 - Dimethyl
Example :
heptane.
5. When more than one type of alkyl groups are CH3
1 2 3 4 5 6
present, then they are to be mentioned in CH3 C CH2 CH CH2 CH2
alphabetical order i.e., ethyl before methyl, and
bromo before chloro. CH3 CH3
Example :
2, 2, 4 - Trimethyl hexane.
CH3 9. The branched chain substituents are numbered
starting from the carbon attached directly to the
CH3 CH2 CH CH CH2 CH2 CH2 CH3 parent chain.
1 2 3 4 5 6 7 8
CH2 The name and numbering of branched substituent
is written in brackets in order to separate it from
CH3 the numbering of the main chain.
4 - Ethyl - 3 - methyl octane

Example :
Main chain
CH3 
1 2 3 4 5 6 7 8 9
CH3 CH2 CH2 CH C CH2 CH2 CH2 CH3
1
CH CH3
Side chain  2
CH3 CH3
4 - (1 - methylethyl) - 5, 5 - dimethylnonane.
Since in IUPAC nomenclature, isopropyl is also included, it can also be written as
4 - isopropyl - 5, 5 - dimethylnonane.
10. When the parts of a name are substituents of a basic structure, then the name is always written in one word.
Correct punctuation is to be followed. Numbers are always to be separated by commas, and name and
number are to be separated by hyphens (-), one should be cautious in giving the correct ending to the name.
After knowing the basic rules of naming of hydrocarbon compounds by IUPAC nomenclature, let us consider
some complicated structures.
1. 2. 1
1 CH3 CH3 CH3 CH3
1 2 3
CH3 C C CH2 CH3 2 CH CH3 CH3
4 3
CH3 CH2 CH3 CH2 C CH CH2 CH2 CH
5 4 5 6 7
C H CH2 CH3 CH3
6
CH3 CH3
3 – Ethyl – 2, 2, 3, 5 – tetramethyl hexane 3, 3 – Diethyl – 2, 4, 7 – trimethyl octane
3. 1 2 3 4 5 6 4. 1 2 3 4 5
CH3 CH2 C C CH2 CH3 CH3 CH CH CH CH3
H H CH3
3 – Hexene 4 – methyl –pent-2-ene
Numbering is given to have the least number to the carbon atom bearing double bond.
Thus the IUPAC name is 4 - methyl - 2 - pentene.
5. 5 4 3 2 1
CH3 CH2 CH C CH
CH3
3 – Methyl – 1 – pentyne
11. When the organic substance contains more than one functional group, one functional group is taken as the
main group in the carbon chain and the other groups are considered as substituents. Consider the following
example CH3 – CH = CH . CH2OH. This is to be named as 2-ene-l- butanol. The alcoholic group is given
preference over double bond. In the table below the order of preference of functional groups is given.
ORDER OF PREFERENCE OF FUNCTIONAL GROUPS
Parent name of the Functional Parent name of the
Functional group
compound group compound
1. Carboxylic acid – COOH 7. Ketone CO

2. Acid chloride – COCl 8. Alcohol – OH
3. Amide – CONH2 9. Amine – NH2
4. Ester – COOR l 10. Chloro compound – Cl
5. Aldehyde – CHO 11. Ether – OR
6. Nitrile – CN 12. Alkene C=C
13. Alkyne –C  C –
E.g.:
1. CH3 – CHBr. CH2. CHOH – CH3 - 4 bromo 2 pentanol.
2. CH2OH . CH2 . COOH – 3 hydroxy propanoic acid
When ketonic group forms a substituent it is named as oxo.
3. CH3 . CO . CH2 . CH2COOH - 4 oxopentanoic acid
4. When aldehyde group forms a substituent it is named as formyl.
CH3 CH CH2 COOH 3 formyl butanoic acid.
CHO
C 2H 5 CH3
F ormative Worksheet | |
43. Give the IUPAC names of the following alkanes : vi) CH3CH2CH – CH – CH2CH2CH – CH3
i) |
CH3  CH  CH  CH3
CH3 – C – CH3
C2H5 C2H5 |
CH 3
H3 C C2 H5
ii) CH3CH 2– C  CH  C H vii) CH3CH2CH2CH2CHCH 2CH2CH2CH3
2 5
C H2 CH2CH3
|
CH2C(CH3)3
44. Draw the structures of the following compounds :
CH3
i) 2-Chlorohexane
|
ii) 6-Hydroxyheptanal
iii) (CH3) 3CCH 2CH2CHCH2CH3
iii) Hex-3-en-1-oic acid
iv) 2-Chloro - 2 methylbutan - 1 - ol
iv) CH3CH2CH 2CHCH2CH2CH 3
v) 5, 5 -Diethylnonan - 3 - ol
|
45. Give the IUPAC names of the following
C(CH3)3
compounds :
CH3 CH 3
v)
| |
i) CH3CH2CH2 – C – CH2 – C = CH2
|
C2H5
CH3
|
ii) CH3 – CH – C  CH iii) C6H5 – CH = CH – CH2Cl
iv) CH3CH = CH – CH2Br
Cl CH2CH3
| |
v) CH2 = C – CH = CH2 vi) CH2 = CH – CH – C = CH2
|
Cl
46. Name each of the following alkanes by the IUPAC system.
CH3 CH3
i) CH–CH2 – CH2 – CH CH3CH3
CH3 CH3 | |
ii) CH3 – C – CH – CH3
|
CH3
C2H5 CH3 CH3CH2

iii) CH–CH2–CH
CH3 CH3 iv) CH–CH3
CH3CH2
v) CH 3CHCH2CH2CHCH2CH 3
| | vi) H3CCH – CH – CH3
CH3 CH3 | |
C3H7 C2H5
(expand C2H5 and C3H7)
vii) (CH3)3C – CH3

C2H5CH3
| |
viii)CH3CH2CH2CH – CHCH2CH3
47. Give the IUPAC names of the following CH3

compounds : |
i) C2H5 – C – CH2OH x) CH3CH2 – C(Cl) – CH2 – CONHCH2CH3
P
CH2 OCH3
|
ii) CH3 – CH = CH – CHO xi) CH3 – CH – CHO
iii) NH2 – CH2 – CH2 – CH2 – NH2
iv) CH3 – CH = CH – COOH xii) [(CH3)2CH]3COH
v) (CH3)2 C = CHCOCH3
vi) CH2 = CH – CN xiii) CH3CH2CHCH2CHO
vii) OCH – CHO |
viii)HOOC – C  C – COOH CH3
xiv) CH3CHCH2CH3
CH3 |
| COOH
ix) CH2 = C – CHOOCH3
48. Give IUPAC names of the following :
CH3
|
i) CH3CH2CH – CH2 – CH2 – CH – CH2 – C – CH3
| | |
CH3 CH – CH3 CH3
|
CH2 – CH3
ii) CH3 – CH2CH2 – CH2 – CH – CH2 – CH2 – CH2 – CH2 – CH3

|
CH – CH3
|
CH – CH3
|
CH3
CH3 CH3
| |
iii) CH 3 – CH – CH2 – CH – CH2 – CH2 – CH2 – C – CH3
| |
CHCH2CH3 CH3
|
CH2CH3
C2H5 CH3
| |
iv) CH3 – CH2 – CH – CH – CH2 – CH2 – CH – CH2 – CH3
|
CH3 – C – CH3
|
CH3
Conceptive W orksheet
42. Give the IUPAC name of the saturated hydrocarbon having the following carbon skeleton.
C–C–C–C–C–C–C
| | | |
C–C–C C C C
43. Give IUPAC names of the following compounds :
i) CH2 = CH–CH2 – CH = CH2 ii) CH3CH2–CH–CH – CH = CH2
| |
C2H5 CH3
CH3
|
iii) CH3C  C – C  C – CH3 iv) CH3 – CH2 – C – CH = CH – CH3
|
CH3
v) CH3 – CH – C = CH2
| |
CH3 C2H5
44. Give the IUPAC name for the amine.
CH3
|
CH3 – N – C – CH2CH3
| |
CH 3C 2H 5
45. Name the following compounds according to the IUPAC system :
i) CH3 – CH – CH3 ii) CH2= C = CH2

|
CH3 – C = CH2
ii) (C2H5)2 C = C(C2H5)2 iv) CH2 = CH – CH = CH – CH = CH2

46. Write systematic names (IUPAC) of the following compounds :
i) CH3 – CH2 – CH2 – CH – CH = CH2
|
CH2 – CH3
O
P
ii) CH3– C – CH2 – CH2 – CH3
Cl
|
iii) CH3CH – C – CH2OH
| |
Cl Cl
47. What is wrong the following names ? Draw the structures they represent and give their correct names.
i) 1, 1 –Dimethylpentane ii) 2 – Methyl –2– propylhexane
iii) 3–Dimethylpentane iv) 5 ethyl - 4, 4–Dimethylpentane
13. Nomenclature of Alicyclic Compounds

These compounds contain one or more rings of three or more carbon atoms and resemble aliphatic compounds
in their characteristics. These are, therefore, called aliphatic cyclic or alicyclic compounds
Monocyclic compounds :
The name of alicyclic compounds are based on the following rules.
1. The names of the alicyclic compound are obtained by adding there primary prefix ‘cyclo’ to the word root
that corresponds to the number of carbon atoms in the ring.
For the cyclic compounds containing all single bonds in the ring, primary suffix ‘ane’ is added to the word
root. For those containing one double or triple bond, the primary suffix ene or yne is added.
2. If only one substituent is attached to the ring, its
position is note mentioned. If two or more
substituents are present, their positions are
indicated by arabic numerals i.e., 1,2,3,4 ........ etc.
which are used for numbering the carbon atoms in
the ring. The numbering is done in such a way
(clockwise or anticlockwise) that the substituents
get the lowest set of locants. All other rules relating 5. If the ring contains lesser carbon atoms than the
to aliphatic or acyclic compounds are then alkyl group attached to it, the compound is named
followed. For example. as the derivative of alkane and the ring is treated
as cycloalkyl substituent. Otherwise, it is named
as the derivative of cycloalkane. For example.
3. If a multiple bonds and some other substituents

are present in the ring, the numbering is done in
such a way so as to assign lowest number to the In case, the side chain contains a multiple bond or
multiple bond. For example a functional group, the alicyclic ring is treated as
NO2 the substituent irrespective of its size. For example,
6. If the ring contains fewer carbon atoms than the

4. In case, some functional group along with some alkyl group attached to it or when more than one
substituents are present in the ring, the numbering ring system is attached to a single chain the
of the carbon atoms should be done in such a way compound is named as a derivative of alkane and
so that the functional group gets lowest number. the ring is treated as cycloalkyl substituent.
7. When both ring as well as side chain contains the
same functional group, then the parent
hydrocarbon is decided on the basis of the number
of carbon atom.
In case, the functional group directly attached to 8. If a compound contains an a cyclic ring as well as
the ring contains carbon atom, suitable suffixes are a benzene ring, it is named as a derivative of
used to represent such a group. benzene.
Functional group Suffix
–COOH Carboxylic acid F ormative W orksheet
–CHO Carbaldehyde
–CºN Carbonitrile
–COCl Carbonylchloride
–CONH 2 Carboxamide
–COOR R—Carboxylate
49. Statement I: is ethyl
A few example are given to represent these :
cyclopentane.
Statement II: When the ring contains more or equal
number of carbon atoms than the alkyl group
attached to it, then it is named as a derivative of
cyclohexane and the alkyl group is treated as
substituent.
1) Both Statements are true, Statement II is the
2)Both Statements are true, Statement II is not 55. Statement I:
3)Statement I is true, Statement II is false. is 1–cyclohexyl pent–1–en–3–one.
50. The IUPAC name of the compound
Statement II: is hydroxy
cyclopentane.
1) 4-(1-methyl-2-hydroxypropyl)-1-cyclopentene
2) Both Statements are true, Statement II is not
2) 3-(1-hydroxy-2-methylpropyl)-1-cyclopentane
3) 2-(cyclopent-3-enyl)-1-propanol
4) 2-(cyclopent-3-enyl)-1-hydroxypropane
51. The IUPAC name of the compound 4) Statement I is false, Statement II is true.
48. The IUPAC name of the given compound
1) 1-Ethyl-3-methyl-4-propyl cyclohexane
2) 4-Ethyl-2-methyl-1-propyl cyclohexane is:

3) 1-Ethyl-5-methyl-4-propyl cyclohexane
4) 1-Ethyl-5-methyl-4-propyl cyclohexane 1) 3-Bromo-5-chloro-1-methylcyclohexanol
2) 5-Bromo-3-chloro-1-methyl-cyclohexanal
52. Hybridisation of carbon atoms in is/ 3) 1-Bromo-5-chloro-3-methyl-3-cyclohexanol
4) 5-Bromo-1-chloro-3-methyl-3-cyclohexanol
are 49. The IUPAC name of the given compound
1) sp3 2) sp2
3) sp 4) sp3d is:
53. The IUPAC name of the given compound
1) Octycyclopentane 2) 3-Cyclopentyloctane
3) Cyclopentaneoctane 4) 6-Cyclopentyloctane
1) 3-Cyclopropane-1-propene 50. IUPAC name of is

2) 3-Cyclopropyl-1-propene
3) 1-Allycyclopropane
4) 3-Allylcyclopropane 1) Propane 2) Cyclo Propane
3) Cyclo propene 4) Cyclo Propyne
51. Statement I: The structure has

54. The IUPAC name of
Three sp3 and Two sp2 carbon atoms.

is:
Statement II: In cyclo alkenes all carbon atoms
1) N-Cyclohexyl benzamide
undrergo sp2–hybridisation.
2) N-Phenyl-N-cyclohexylmethanamide
3) N-Phenylcyclohexane carboxamide
4) N-Cyclohexyl-N-Phenylmethylamide
1) Both Statements are true, Statement II is the 1) 5-Bromo-6-chloro-1-cyclohexene-3-yne
correct explanation of Statement I. 2) 6-Bromo-5-chlorocyclohexen-3-yne
2) Both Statements are true, Statement II is not 3) 6-Bromo-5-chloro-3-cyclohexen-1-yne
correct explanation of Statement I. 4) 4-Bromo-3-chloro-3-cyclohexen-5-yne
52. IUPAC name of
57. The IUPAC name of
1) Cyclodecane 2) Cyclododecane
3) Decane 4) Dipentane
1) 1–cyclobutyl pentane 58. IUPAC name of the following compound
2) 1–pentyl cyclobutane
3) cyclobutyl cyclopentane
4) cyclopentyl cyclobutane
53. IUPAC name of 1) 1-(2-Butyl) cyclohexane

2) 1-(3-Butyl) cyclohexane
3) 2- Cyclohexylbutane
1) 2–cyclo propyl butane 4) 3-Cyclohexlbutane
2) 2–cyclobutyl propane 59. Which of the following is/are correct
3) 2–cyclo butyl cyclopropane
4) propyl butane
54. IUPAC name of

1)
1) 3–cyclo butyl pentane

4) 2,3–diethyl cyclobutane
2)
1) cyclopropane
2) cyclobutane
3) cyclopentane
3)
4) cyclohexane
56. The IUPAC name of the given structure

4) All the above
is :
14. IUPAC Names of polycyclic next longest bridge to the first bridge head and
finally ends at the substituted carbon along the
compounds
shortest path. For example,
Certain cyclic compounds contain two or more rings.
The IUPAC names of each compounds are based
upon the following guidelines .
1. The carbon atoms common to the two rings are
known as bridge head atoms . Each bond or chain
of carbon atoms which connects the bridge head
atoms is known as bridge. The bridge may
contain either no carbon atom (0) or carbon
atom (A) or two carbon atoms (B).
This may be illustrated by the following e.g.,
(or)
2. The bicyclic compound is named by attaching the

prefix ‘bicyclo’ to the name of the hydrocarbon Names of spiro bicyclic hydrocasrbons :
in which the root word contains the total number Spiro bicyclic hydrocarbons contain two rings
of carbon atoms involved in the two rings. The consisting of carbon atoms only the two rings are
number of the carbon atoms in the different bridges linked by a common carbon. These compounds
are represented by arabic numerals 0,1,2,3, etc. are named by placing prefix ‘spiro’ before the
These are arranged in a descending order name of the acyclic parent hydrocarbon with same
separated by full stops  g  and enclosed in square number of skeleton carbon atoms. The numbers
of skeleton atoms linked to the spiro atom are
brackets. The complete name of the hydrocarbon indicated by arabic numbers, separated by a full
is written by placing the bracket between the prefix stop. The numbers are written in ascending order
and the name of the hydrocarbon. and enclosed in square brackets.
For example, Numbering of a spiro bicyclic hydrocarbon starts
with a ring carbon next to the spiro atoms and
proceeds first through the small ring and then
through the spiro atom and around the second ring.
Some examples are given below :
If a substituent or double bond is present in one of

the rings, then the bicyclic ring is numbered in
order to ascertain its position. The numbering
begins with one of the bridge head atoms,
proceeds first along the longest bridge to the
seconds bridge head atoms, continues along the
63. The IUPAC name of the following
56. The IUPAC name of the following compound
1) Bicyclo [0.2.2.] hexane
2) Bicyclo [ 2.2.0 ] hexane
is 3) Bicyclo [ 2.0.2 ] hexane
4) Bicyclo [ 2.0.0 ] hexane
64. The IUPAC name of the following compound
1) Bicyclo [ 2. 2. 0] octane
2) Bicyclo [0. 2. 2 ] hexane is
3) Bicyclo [ 2. 1. 1 ] hexane
4) Bicyclo [ 2. 2. 0] hexane 1) Bicyclo [ 1.1.0 ] butane
58. The IUPAC name of the following compound 2) Bicyclo [ 1.0.1 ] butane
3) Bicyclo [ 0.1.1 ] butane
4) Bicyclo [ 0.1.0 ] butane
is 65. Select the correct IUPAC name of the following
compound
1) Bicyclo [ 1. 2. 3 ] octane
2) Bicyclo [ 3. 2. 1 ] octane 1) 1, 1 – Cyclobutyl heptane
3) Bicyclo [ 2. 3. 1 ] octane 2) Bi cyclo [6.3.0] nonane
4) Bicyclo [ 2.3. 0 ] octane 3) spiro [3.6] decane
59. Which of the following is a spiro-compound? 4) spiro [6.3) decane
Column-I Column-II
66
For spiro compounds
a) Two fused rings 1) Three
b) The number of bridges 2) Two
in bicyclo compounds
c) The number of bridge 3) One
60. In the nomenclature of spiro-compounds the hea ds in bicyclo
number of carbon atoms in the ring is written in compounds
brackets in _________ order. d) In bicyclo compounds 4)Bicyclo
1) Ascending 2) Descending two rings are joined by compounds
3) Decreasing 4) No particular
61. The two rings in spiro compounds are joined by
__________ Conceptive W orksheet
1) 1º 2) 2º 60. If two rings are joined by a quaternary carbon at
3) 3º 4) 4º the apex then the names of the compounds are
prefixed by _______
1) Cyclo 2) Bicyclo
3) Spiro 4) Bispiro
62. The IUPAC name of 61. Statement I: In the spiro compounds the
numbering of carbon atoms starts from the atom
next to spiro atom.
1) bicyclo [ 4.3.1 ] decane Statement II: In numbering the carbon atoms in
2) bicyclo [ 3.2.0 ] nonane spiro compound, it proceed through the smaller
3) bicyclo [ 2.2.2 ] decane ring first.
4) bicyclo [ 3.3.0 ] nonane
1) Both Statements are true, Statement II is the 1) Both Statements are true, Statement II is the
correct explanation of Statement I. correct explanation of Statement I.
2) Both Statements are true, Statement II is not 2) Both Statements are true, Statement II is not
correct explanation of Statement I. correct explanation of Statement I.
3) Statement I is true, Statement II is false. 3) Statement I is true, Statement II is false.
4) Statement I is false, Statement II is true. 4) Statement I is false, Statement II is true.
62. Column-I Column-II 65. The systematic name of the compound
For spiro compounds
a) No. of rings 1) Smaller ring first
b) No. of carbon atoms
at the apex 2) 2
c) Numbering the 1) 8 – methyl bicyclo[1.2.3) octane
carbon atom 3) Ascending 2) 8 – methyl bicyclo [3.2.1) nonane
d) Numbering starts with 4) One 3) 8 – methyl bicycle [3.2.1) octane
5) Three 4) none of the above
63. Compounds containg two fused rings are named 66. Column-I Column-II
as __________ a) Two rings are joined by 1) 2
1) Alkenes 2) Arenes b) The number of quaternary
3) Bicyclo compounds 4) Paraffins carbon atoms 2) 1
64. Statement I:The name of bicyclo compound c) The number of rings 3) 4O carbon
d) Numbering starts from 4) Smaller ring
is bicyclo [1, 1, 0] pentane. 5) Larger ring
Statement II: In bicyclo compounds there are three
carbon bridges.
15. Isomerism
Different organic compounds with the same molecular formula but different physical and chemical properties
are called isomers and the general phenomenon is known as isomerism. It is classified as follows.
16. Structural Isomerism

Compounds which possess the same molecular formula but differ in bonding arrangement of atoms (or)
groups within the molecule i.e. differ in structure [A structural formula for a compound conveys which atom
is directly linked to which other atom. It, however, tells nothing about the shape of the molecule but indicates
the groups of elements present which provide clues to the properties of the substance], are structural
isomers and this phenomenon is known as structural isomerism.
(i) Chain or Nuclear Isomerism:
In this type the isomers differ in the variation of the carbon chain (or) skeleton of the molecule. The same
molecular formula may represent a straight chain of carbons as well as a branched chain. The molecular
formula C4H10 stands for two isomers namely n-butane and isobutane.
Cyclohexane and methyl cyclopentane are nuclear isomerism
Illustration 1 : Give the possible chain isomers for propyl benzene.
Solution :
Illustration 2 : Give the possible chain isomers for C5H13N
Solution :
(ii) Position Isomerism :

In this, the isomers differ in the attachment of the functional group (or) substituents to the carbon chain.
This is illustrated by the following examples.
Illustration 3 : Give the possible positional isomerism for di chlorobenzene.

Solution :
Note :In the aromatic series, the disubstitution products of benzene also exhibit isomerism due to different
relative positions occupied by the two substituents on the benzene ring.
(iii) Functional Isomerism :
If the molecules have the same molecular formula but differ in the type of the functional group , then it is
known as functional group isomerism. A few examples of functional isomers are:
b) Monocarboxylic acids and esters are functional isomers
c) Aldehydes, ketones, unsaturated alcohols and alkene oxides are functional isomers.
(iii) Cyanides are isomeric with isocyanides. RCN (Alkyl cyanide) RNC (alkyl isocyanide)
(iv) Nitroalkanes are isomeric with alkyl nitrites
(v) Aromatic alcohols may be isomeric with phenols
(vi) Sometimes a double bond containing compound may be isomeric with a triple bond containing
compound. This is also called as functional isomerism. Thus butyne is isomeric with butadiene
(Molecular formula C4H6)
(vii) Primary, secondary and tertiary amines of some molecular formula are also the functional isomers.
Illustration 4 : Give the functional isomer for acetic acid
Solution :
Monocarboxylic acids and Ester’s are functional isomers.

Illustration 5 : Give the functional isomer for acetaldoxime.
Solution :
Oximes and amides are functional isomers.

Illustration 6 : Give the functional isomer for ethyl thioalcohol.
Thioalcohols and thio ethers are functional isomers.

(iv) Metamerism :
It arises when different alkyl radicals are joined with the same divalent functional group present in the
molecule, e.g. ethers, thioethers, secondary amines, ketones, esters etc.
Illustration 7 : Give the metamer for ethyl propionate.
Solution :
(v) Ring Chain Isomerism:

This type of isomerism is due to difference in way of linking of carbon atoms and the isomers may have
either open chain (or) closed chain structure e.g. alkenes and cycloalkanes.
Note: Ring chain isomers are always functional isomers.

VI. Tautomerism
This type of isomerism is due to spontaneous interconversion of two isomeric forms with different functional
groups into one each other.
The term tautomers means “constitutional isomers that undergo such rapid interconversion that they cannot
be independently isolated.
a) Isomer are called tautomers.
b) Tautomers exist in dynamic equilibrium
c) Conversion is acid and base catalysed
d) In presence of acid or base, ketone or aldehyde with  -hydrogen is converted into hydrocy ene (called
enol), hence this type of isomerism in which keto and enol forms exist in dynamic equilibrium is also called
keto-enol isomerism
74. Which of the following pairs are chain isomers.

Formative W orksheet
67. Which of the following pairs of functional group
exhibit functional isomerism.
1) – CHO and C=O
2) – OH and – O –
3)  NH 2 and – NH –
4) – COOH – COOR
68. Match row-1 with row-2
Row-1
a) Functional isomers
b) Metamers
c) Positional isomers
d) Chain isomers
Row-2
1) C2 H 5  NH  C2 H 5 & CH 3  NH  C3 H 7
2) CH 3  CH 2  CH 2  Cl & CH 3 - CH-
|
CH 3
Cl 67. Statement I: Diethyl ether and methyl propyl ether
3) CH 3  CH 2  NH 2 & CH 3  NH  CH 3 are metamers.
Statement II:Functional isomers have same
4) CH 3  CH 2  CH 2  CH 3 & CH 3 - C| H- CH 3 molecular formula and same functional group
CH 3
69. Which of the following pairs shows isomerism? correct explanation of Statement I.
1) CH4 and C2H6 correct explanation of Statement I.
2) CHCl3 and CCl4 3) Statement I is true, Statement II is false.
3) CH3CH2OH and CH3OCH3 4) Statement I is false, Statement II is true.
4) NaCl and KCl 68. An isomer of ethanol is:
70. Which of the following compounds can exhibits 1) Methanol 2) Acetone
chain isomerism 3) Diethyl ether 4) Dimethyl ether
1) Butane 2) Propane 69. An alkane forms isomers if the minimum number
3) Pentane 4) Hexane of carbon atoms is:
71. Which of the following are chain isomers? 1) 4 2) 3 3) 2 4) 1
70. CH 2  CH  CH  CH 2 and
1) CH3CH2CH3 and CH3CH2CH2 CH3
2) CH3CHCl2 and CH2Cl CH2Cl H 3C  C  C  CH 3 are
3) CH3CH2CH2OH and CH3CH2OH
1) Functional isomers 2) Position isomers
4) CH3CH2CH2 CH3 and (CH3)2CHCH3
3) Metamers 4) Both 1 and 2
72. Which of the following shows functional
71. Which of the following are functional isomers?
isomerism?
1)CH3CH2Cl and CH3CH2Br 1) CH 3  O  CH 3 & CH 3CHO
2) CH3CHBr2 and CH2Br CH2Br
2) C2 H 5OH & CH 3  O  CH 3
3)C2H5O C2H5 and CH 3OC3H 7
4) CH3CH2CHO and CH3COCH3 3) CH 3  CN & C2 H 5  CN
73. The number of possible open chain (acycli3)
isomeric compounds for molecular formula C5H10 4) CH 3Cl & CH 3 Br
would be
1) 8 2) 7 3) 6 4) 5
72. Which of the following functional groups exhibit about the bond is restricted. Due to restricted
Metamerism rolation the plane of the double bonded C-atoms
1) Keto group 2) Ester becomes rigid i.e., fixed with respect to each
3) Secondary amine 4) All other. The spatial arrangement of the groups on
73. Statement I:Neopentane and Isopentane are chain the double bonded carbons is fixed. When each
isomers double bonded carbon atoms are bonded to
Statement II: Chain isomers have same carbon different groups basing on their s p a t i a l
atom chain length. arrangement two isomers known as geometrical
1) Both Statements are true, Statement II is the isomers are possible. The phenomenon is known
correct explanation of Statement I. as geometrical isomerism.
2) Both Statements are true, Statement II is not When both groups attached to a double bonded
correct explanation of Statement I. carbon atoms are same no configurational
3) Statement I is true, Statement II is false. isomers are possible hence the compound having
the formula a2C  Cbd does not show
74. How many structural isomers are possible for
organic compound having formula C4H10 O? geometrical isomerism.
1) 4 2) 5 3) 6 4) 7
75. How many structural isomers are possible for
organic compound having molecular formula C4H8 ?
1) 4 2) 5 3) 6 4) 7
76. Isomers have
1) Same molecular formula are not geometrical isomers
2) Similar physical properties When double bonded carbon is bonded to two
3) Similar chemical properties different groups and same set of groups are
4) Different physical and chemical properties present on the other carbon atom also then the
77. The total number of isomeric alcohols with the possible configurations are
molecular formula C4H9OH is
1) 2 2) 3 3) 4 4) 5
17. Stereo Isomerism

Substances having the same molecular formula The isomer which has similar groups on the same
and same stnucture but differ in the spatial side of the plane of double bond is known as cis
arrangement of atoms or group of atoms are isomer
known as stereoisomers. The isomer which has similar groups on the oppsite
Stereoisomerism is of two types configurational sides of the plane of double bond is known as
and conformational. trans isomer.
Configurational isomers possess certain type Examples:
of rigidity in the molecule. Configurational isomers
can be interconverted only by bond breaking and
reforming of the bonds. Conformational isomers
known as conformers are interconverted by
rotation about the bonded atoms along with the
groups present on them. Configurational isomers
are of two types geometrical isomers and optical
isomers
Geometrical Isomerism
When a molecule contains  -bonded C-C atoms
free rotation of the bonded atoms along with the
groups present on them making the bond as axis
is possible. When a molecule contains double
bonded carbons the rotation of the bonded carbons
atom are arranged in order of priority basing on

sequence rules.
E and Z system of nomenclature : “Cis” and
‘trans’ designations cannot be used for highly
substituted alkenes if four different atoms or
groups are attached to the carbon atoms of a
double bond.
a d
C C
b e
In such cases, E and Z system of nomenclature is
used. This system is based on a priority system
developed by Cahn, Ingold and Prelog.
In this system, the two atoms or groups attached
to each of the doubly bonded carbon are put in
In case of compounds with the formula abC=Cad
order of precedence (priority) on the basis of
cis and trans configurations are
sequence rules.
distinguished basing on the spatial arrangement
(i) The symbol ‘E’ is assigned to an isomer in
of common group a.
which the atoms or groups of higher precedence
are on the opposite side (E from German
word, Enfgegen = across or opposite).
(ii) The symbol ‘Z’ is assigned to an isomer in
which the atoms or groups of higher precedence
are on the same side (Z from German word,
Zusammen = together).
   
C C C C
Pent-2-ene Cis pent-2-ene  E-isomer   Z-isomer 

crotonic acid and iso crotonic acid Note : 1 signifies higher precedence and 2 signifies
lower precedence. in most of the cases ‘Z’
corresponds to cis-form and ‘E’ to trans-form.
However, there are many exceptions.
Sequence rules :
The following rules are followed for deciding the
precedence order of the atoms or groups.
(1) Higher priority is assigned to the atoms of higher
atomic number. For example, the order of
precedence in the following atoms,
H, Cl, I, Br is:
I (Z= 53)>Br(Z= 35)>C1 (Z= 17)>H(Z= 1)
(2) If isotopes of the same element are attached, the
If all the four groups attached to the double bonded
isotope with higher mass number is given higher
carbon atoms are different to
order of precedence. For example, deuterium
distinguish geometrical isomers E-Znotational
system is used  D is assigned higher priority in comparison to
2
1
This system was developed by Cahn Ingold and
hydrogen  H .
1
prelog. 1
The groups attached to each double bonde carbon
(3) In the groups, the order of precedence is also 1. FCl C = CBr I,

decided on the basis of atomic number of first the priority order is F<Cl, Br<I
atom of the group. For example, in the following
set,
—Cl, —OH, —COOH, —NHCH3, —SO3H
The order of precedence is:
 Cl >  SO3H >  OH >  NHCH3 >  COOH
     2 Cl(OH)C=CICOOH
(Z =17) (Z =16) (Z =8) (Z =7) (Z =6) priority order is -OH<-Cl;-I
When the order of precedence of the groups
cannot be settled on the first atom, the second
atom or the subsequent atoms in the groups are
considered. For example, in the set —CH2 —CH3,
— CH 3 , —COOH, the order cannot be
3 CH 3ClC  CbrCH 2CH 3
decided on the basis of first atom as it is same in
all the groups. However, in —CH 2—CH 3, the priority order is CH 3  Cl ; CH 2CH 3   Br
second atom is carbon, in —CH3, the second atom
is hydrogen while in —COOH, the second atom
is oxygen. Hence, the order of precedence is:
 COOH >  CH2  CH3 >  CH3
   Geometrical isomerism is also exhibited by the
(Z = 8) (Z = 6) (Z = 1) compounds containing >C=N and -N=N-bonds and also
(4) A doubly or triply bonded atom is considered by alicyclic compounds.
equivalent to two or three such atoms. For Eg:
example,
>C- O
the group >c = o is equal to 

and the group -C  N is equal to

-C -N


N
The geometrical isomer in which the higher priority

atom /groups are on the opposite sides of plane of
General properties of geometrical
C=C then it is E-isomer . The geometrical isomer isomers:
in which the higher priority atom / groups are on 1. Geometrical isomers mainly differ in physical
the same side of plane of C=C then it is Z-isomer. properties
For the compound abC=Cde, if a<b and d<e then 2. Trans isomer has molecular symmetry while cis
isomer is unsymmetric.
3. For trans   o while for cis   o
4. Generally cis isomer has lower M.P, lower B.P,
and higher solubility than trans isomer
5. Geometrical isomers can be seperated by
fractional crystalisation, fractional distillation or
chromatography.
6. Cis and trans isomers possess similar but identical
chemical properties.
Reason for the C=C to show space isomerism:

A double bond between two carbon atoms consists one sigma (  ) bond and one pi (  )bond. Both the carbon
atoms aresp2-hybridized, giving three hybrid orbitals each. One p-orbital of each of the carbon atoms is left as
such, i.e., it does not take part in hybridization. The sigma bond between the two carbon atoms is formed by overlap
of one hybrid orbital of each of the carbon atom, while  -bond is formed by the overlap of one p-orbital of each
carbon atom.
Like the p-orbitals, a  -bond has two lobes. One half of the n-bond lies above the plane containing the two nuclei
and other half lies below the plane (The two carbon atoms and four hybrid orbitals lie in the same plane while the
lobes of
 -bond lie above and below this plane). Rotation around  -bond is not possible. If any attempt is made to rotate
one of the carbon atoms, the lobes of p-orbitals will no longer remain coplanar, i.e., no parallel overlap will be
possible and thus,  -bond will break and it requires the energy of the order of 251 kJ. This is known as concept of
restricted rotation. In other words, the presence of  -bond makes the position of two carbon atoms rigid, i.e., fixed
with respect of each other. The restriction in rotation makes the position of four groups attached to two carbon
atoms (two groups linked to each carbon atom utilising hybrid orbitals} fixed in space and is responsible for space
isomerism known as geometrical isomerism.
So in general, the geometrical isomerism is shown by alkenes or their derivatives in which two different atoms or
groups are attached to each carbon containing double bond and carbon atoms joined by double bond cannot rotate
freely.
Let us consider now the various groups linked to two carbon atoms joined by a double bond.
1st Case: When two groups attached to a carbon atom are same,
aCa aCa aCa aCa
 or   or 
aCb bCa bCd dCb
(I) (II)
Both the structures are identical Both the structures are identical
Geometrical figures in (I) and (II) will be identical, hence, no geometrical isomers are possible.
2nd Case : When two groups attached to a carbon atom are different,
bCa bCa bCa bCa bCa bCa
 or   or   or 
bCa aCb dCe eCd dCa aCd
(III) (IV) (V)

Non-Identical Non-Identical Non-Identical
The two geometrical figures [as shown in (III), (IV) and (V)] will be different and hence, geometrical isomers are
possible.
Such isomers, which possess the same molecular and structural formula but differ in the arrangement of atoms or

groups in space due to hindered rotation around the double bonded atoms, i.e., >C = C, >C = N and -N = N 
are known as geometrical isomers and the phenomenon is known as geometrical isomerism. The
isomer which has similar groups on the same side of the double bonded carbon is called ‘cis’ isomer (Latin : cis=
same side) and the isomer which has similar groups on the opposite side of the double bond is known as ‘trans’
isomer (Latin : trans = across). However, in cases where all the four groups are different (abC=Cde), it is not
possible to decide the cis and trans isomers.
The compounds like, 1,2-disubstituted alkenes and unsaturated dibasic acids are capable of showing geometrical
isomerism.
Examples:
(i) (1, 2, Dichloroethene) (ii) But-2-ene (CH3CH=CHCH3)
H H H Cl CH3 CH3 CH3 H

C=C C=C C=C C=C
Cl (Cis) Cl Cl (Trans) H H (Cis) H H (Trans) CH3
(iii) Maleic and fumaric acids
HOOC COOH HOOC H

C=C C=C
H H H COOH
Maleic acid (Cis) Fumaric acid (Trans)
(iv) Pent-2-ene
CH3 C2H5 CH3 H

C=C C=C
H H H C2H5
(Cis) (Trans)
(v) Hex-3-ene
C2H5 C2H5 C2H5 H

C=C C=C
H H H C2H5
(Cis) (Trans)
(iii) In contrast cyclohexane shows three position isomers (1,2; 1,3; 1,4-) each has two geometrical
forms, e.g.,
H H H CH3
H H CH3 H
CH3 CH3 CH3 H

CH3 CH3 H CH3
(Cis) (Trans)
(Cis) (Trans)
1, 2-Dimethyl cyclohexane 1, 4-Dimethyl cyclohexane
(d) Alkadienes:For example, hexa-2,4-diene shows different cis and trans isomers.
cis cis trans
trans
cis trans trans
cis
Properties of Cis and Trans isomers:

Properties : Cis and trans isomers have different physical properties such as melting points, boiling points,
solubilities, dipole moment, stability and densities, etc. The trans isomer, in general, has a higher melting point
and a lower boiling point.
But-2-ene
H H H CH3
C=C C=C
H3C CH3 H3 C H
B.P = 277K B.P = 274K
(cis) (trans)
Maleic acid and fumaric acid:

77. Which of the following statements is not true
regarding the cis and trans isomers of an alkene?
H H H COOH
1) They are configurational isomers.
C=C C=C 2) They are diastereiomers
HOOC COOH HOOC H 3) The cis-isomer has higher dipole moments than
m.pt. 403 K m.pt. 575 K the trans isomers.
The cis-isomers have higher solubilities. In general, 4) The cis-isomer usually has a lower boiling point
cis-isomers have the higher dipole moment. trans-2- than the trans isomers.
butene and trans-dichloroethylene possess nearly zero 78. Statement I:Metamers can also be chain or position
dipole moment while the cis-forms have significant dipole isomers.
moment as similar groups are attached to the same side Statement II: The term tautomerism was
of the double bond and combined inductive effects are introduced to explain the reactivity of a
additive. They differ in adsorption capacity on materials substance according to two possible structures.
used in chromatography. They can be separated by the 1) Both Statements are true, Statement II is the
techniques of fractional distillation, fractional correct explanation of Statement I.
crystallisation or chromatography. In general, trans- 2)Both Statements are true, Statement II is not
isomers are more stable than the corresponding cis- correct explanation of Statement I.
isomers. The stearic repulsion of the groups (same) 3) Statement I is true, Statement II is false.
makes the cis-isomer less stable than the trans-isomer 4) Statement I is false, Statement II is true.
in which the bulky groups are far apart. Cis-trans isomers 79. Which of the cycloalkanes will show cis-trans
are called diastereomers as they are not mirror images isomerism?
of each other.
Cis-trans isomers have similar but not identical chemical
properties. For example, maleic acid (cis-isomer) forms
anhydride on heating while fumaric acid (trans-isomer)
does not give anhydride. This means that in maleic acid,
the two —COOH groups are on the same side of double
bond and on this basis the configuration of maleic and
fumaric acid can be established.
H  C  COOH H  C  CO
 
403K
 Heat 
  O + H2O
H  C  COOH H  C  CO
(Cis) Maleic acid Maleic anhydride
Formative W orksheet 80. Cis-2-Butene and trans-2-butene are

1) Geometrical isomers
75. The isomeric cis - 2 butene and trans - 2 butene 2) Diastereomers
can be distinguished on the basis of 3) Enantiomers
1) Their physical properties 4) Position isomers
2) Their reduction products 81. The IUPAC name of the compound:
3) The products they give on ozonolysis
4) The products they give no addition of bromine
76. Which of the following pairs represents
stereoisomerism? 1) (2E, 4E, 6Z) -octa-2, 4, 6 -triene
1) Geometrical isomerism, position isomerism 2) (2E, 4E, 6E) -octa-2, 4, 6 -triene
2) G:eometrical isomerism, conformational 3) (2Z, 4E, 6Z) -octa-2, 4, 6 -triene
isomerism 4) (2Z, 4Z, 6Z) -octa-2, 4, 6 -triene
82. Statement I: CHBr=CHCl exhibits geometrical
3) Optical isomerism, geometrical isomerism
isomerism but CH2Br – CH2Cl does not
4) Optical isomerism, metamerism Statement II: Presence of C=C is one of the
conditions of geometrical isomerism
1) Both Statements are true, Statement II is the 84. The correct name of the structure:
78. Which of the following compounds will exhibit cis- 1) (E), (E) - 2, 4 - hexadiene
trans isomerism? 2) (Z), (Z) - 2, 4 - hexadiene
1) but-2-ene 2) propene 3) (E), (Z) - 3, 5 - hexadiene
3) but-1-ene 4) benzene 4) (Z), (E) - 2, 4 - hexadiene
79. Which compound is expected to show geometrical 85. Match the following
isomerism? Column-1 Column-2
1) CH3 CH=C(CH3)2 2) CH3CH=CH2 a) E-isomer 1) Higher priority on same side
3) CH3CH=CHCH3 4) (CH3)2C=C(CH3)2 b) Z-isomer 2) Higher priority on opposite side
80. Which of the following compounds shows c) Cis isomer 3) Fumaric acid
geometrical isomerism? d) Trans isomer 4) Maleic acid
1) CH2=C=CBr2 2) BrCH=CH=CHBr
3) CH3CH=C=CHBr 4) BrHC=C=C=CHBr
81. Statement I: Alkanes containing more than three Summative W orksheet
carbon atoms exhibit chain isomerism.
Statement II: All the carbon atoms in alkanes are 1. The first organic compound synthesised in the
sp-hybridized laboratory from an inorganic compound is
1) Both Statements are true, Statement II is the 1) NH 4 NCO 2) NH 2  CO  NH 2
2) Both Statements are true, Statement II is not 3) CH 3COOH 4) CH 4
correct explanation of Statement I. 2. The first cabon compound prepared from its
3) Statement I is true, Statement II is false. elements is
4) Statement I is false, Statement II is true. 1) Urea 2) Acetic acid
82. The ‘E’-isomer is: 3) Methane 4) Benzene
3. Organic compounds are numerous since
1) Carbon has high catenation ability
2) Tetravalency of carbon
3) Isomerism of organic compounds
4) All.
4. Energy required for the excitation of carbon atom is
1) 501. 6 KJ/ mol 2) 827.0 KJ/ mol
3) 341.0 KJ/ mol 4) 610.0 KJ/ mol
83. The ‘Z’ isomer is: 5. Hybridisation of carbon atom in CH3 + is
1) sp 2) sp2
3) sp 3
4) sp3d
6. Which of the following has maximum C - H bond
length
1) C2H4 2) C2H2
3) C2H6 4)C6H6
7. Hybridisation at 2nd carbon in CH2 = C - CH3 is
1)sp 2) sp2
3) sp 3
4) sp3d 3
8. Which hybrid orbitals are involved in the CH3- 22. The bonglength of C - C in hydrocarbons follow
CH = CH - CH3 compound the order
1) sp and sp3 2) sp2 and sp3 1) C2 H 6  C6 H 6  C2 H 4  C2 H 2
3) sp and sp2 4) only sp3
9. The ratio of  and  bonds in benzene is 2) C2 H 6  C2 H 4  C2 H 2  C6 H 6
1) 3 :1 2) 4 : 1 3) C2 H 2  C2 H 4  C2 H 6  C6 H 6
3) 1 : 4 4) 2 : 3
10. The ratio of pure and hybrid orbitals 4) C6 H 6  C2 H 2  C2 H 4  C2 H 6
H 2C  CH  CH  CH 2 23. The bond energy of C - C in hydrocarbon follow
1) 7 : 12 2) 14 : 13 the order
3) 6 : 5 4) 5 : 6 1) C6 H 6  C2 H 2  C2 H 4  C2 H 6
11. C- H bond type in benzene is
1)  sp - s 2)  sp2 - s 2) C2 H 2  C2 H 4  C2 H 6  C6 H 6
3)  sp3- s 4)  p - p 3) C2 H 6  C2 H 4  C2 H 2  C6 H 6
12. Which of the following is linear in shape ?
1) Methane 2) Ethane 4) C2 H 6  C6 H 6  C2 H 4  C2 H 2 .
3) Ethene 4) Ethyne 24. Which of the following is an aromatic compound
13. Bond angle in ethene is 1) Phenol 2) Nephtalene
1) 1200 2) 1800 3) Pyridine 4) All
3) 1090 281 4) 111 25. Which of the following is not an organic compound
14. Which of the following does not contains all 1) Furan 2) thiophene
carbons with sp2 hybridised ? 3) Pyrrole 4) Cyclohexane
1) C2 H4 2) C6 H6 26. The % increase of s- character in the hybrid
3) CH2 =CH - CH = CH2 4) CH  C - C  CH
orbitals of carbon in CH 4 , C2 H 4 , C2 H 2 follow
15. In homologous series, the consecutive members
differ in structural formula by the order
1) CH 2) CH3 3) CH2 4) C6 H6 1) CH 4  C2 H 4  C2 H 2
16. Pick out a set of homologous
1) C2 H6, C2 H4, C2 H2, C2 H5 2) C2 H 4  CH 4  C2 H 2
2) C6 H6, C7 H8, C9 H10, C9 H12 3) CH 4  C2 H 4  C2 H 2
3) CH4, C2 H6, C3 H8, C4 H10
4) C2 H2, C3 H4, C4 H6, C4H10 4) C2 H 2  C2 H 4  CH 4
17. According to Huckle's rule a compound is said to 27. Between the two carbon atom, the no. of  & 
be aromatic if it contains
bonds present in C2 H 2 respectively are
1)  4n  2   bonds 2)  4n  2   bonds 1) 1,2 2) 2, 1
3) 5, 2 4) 3, 2
3)  4n  2  C  atom 4)  4n  2   electrons 28. The number of  electrons present in naphthalene
18. Which of the following is alicyclic compound 1) 6 2) 10
1) Cyclopentanol 2) Cyclohexane 3) 5 4) 12
3) Benzene 4) both 1 & 2 29. The hybridisation of carbons C1 and C3 in the
19. Total numbers of hybrid orbitals present in compound
CH3 -C  CH is 1 2 3 4
1) 8 2) 6 3) 4 4) 2 CH3 - CH = CH-CH3
20. The hybridisation of central carbon in 1) sp 2) sp2
CH2= C =CH2 3) sp3 4) nethier of these
1) sp 2) sp2 3) sp3 4) None 30 Which of the following molecular formula belongs
21. Number of  and  bonds present in acompound to the alkyne series ?
of molecular formula C n H 2n 1) C7 H14 2) C10 H22
1) (3n+ 1) ,2 2) (3n-1), 2 3) C9 H16 4) C16 H32
3) (3n - 1),1 4) (3n -3 ), 1
1) 4- hydroxy -2-methyl penatanal

HOTS W orksheet 2) 2- hydroxy -4- methyl pentanal
3) 4- hydroxy -2- methyl pentanol
1. Total number of tertiary hydrogen atoms in 4) 2- hydroxy -4 - methyl pentanol
CH3 - CH- CH2 - CH3 is 10. IUPAC name of
|
CH 3  CH 3 3 C  CH  CH  CHO
1) 1 2) 2 3) 3 4) 4 1) 4, 4, 4 - trimethyl but - 2- en - 1 - al
2. Which of the following compounds does not have 2) 4, 4 - dimethyl pent - 2- enal
any tertiary hydrogen atoms 3) 2, 2 - dimethylpent - 3- en - 4- al
1) (CH3)3CCH2CH3 2) (CH3)2CHCH2CH3 4) 3 - tert. butyl prop - 2- en - 1- al
3) (CH3)2CHCH(CH3)2 4) (CH3)3CH
3. The number & type of carbon atoms present in 11. IUPAC name of HO  CH 2  CH  COOH
|
neopentane are NH 2
1) four 10 carbons , one 40 carbon
1) 3 - hydroxy - 2- aminobutanoic acid
2) two 10carbons , two 20 carbons
2) 2 - amino - 3- carboxypropanol
3) one 10 carbon , one 40 carbon
3) 2- amino - 3- hydroxy- propanoic acid
4) one 10 carbon , one 40 carbon
4) 2- amino - 3- hydroxybutonoic acid
4. In I.U.P.A.C system of naming of organic
12. IUPAC name of
compounds Which of the following functional
groupe has more preference than others (in a CH 3  CH  OCH 3   CH 2  NH 2
poly functional compound ) 1) 2 - methoxy propanamine
1) - OH 2) - CHO 2) 1- amino - 2- methoxy propane
3) - CO- 4) - CONH2 3) 1- amino - 2- methyl - 2- methoxy ethane
5. CH3 COCH2 CN has the I,U.P.A.C.name 4) 1- methoxy - 2- amino propane
1) 3- oxo butane nitrile 2) 1- cynao propane
3) 2- oxo propane 4) 1- cynaobutanone -2 CH 2  CH  CH 2
6. I.U.P.A.C name of CH3 - CH (C2 H5)-CH2 - 13. IUPAC name of | |
CN
|
CN CN
CH(OH)- CH3 is 1) 3 - cyanopentane -1, 5- dinitrile
1) 4- methyl -2- hexanol 2) 4- ethyl -2- pentanol 2) Propane -1,2,3 - tri nitrile
3) 2- ethyl -2- penatol 4) 3- methylhexanol 3) 1,2,3 - tri cyano propane
7. The IUPAC name of (C2 H5) CH .CH CH2 OH 4) Propane - 1,2,3 - tricarbylamine
is 14. IUPAC name of
1) 3 - methyl butanol-1 2) 2- methyl pentanol-
1 3) 3- ethyl penatanol -1 4) 2- ethyl butanol-1 HOOC  CH 2  CH  CH 2  COOH
|
8. IUPAC name is COOH
CH3 1) 3 - Carboxylic pentane - 1, 5 - dioic acid
| 2) Propane - 1,2,3 - trioic acid
3) 1, 2, 3 - tricarboxylic propane
CH3 -(CH2)4-CH- C-CH2 -CH2-CH3 is 4) Propane tri carboxylic acid
15. Which of the following statement is correct?
| | 1) - CH2 - contains secondary carbon atom
CH3 CH2 -CH3 2) IUPAC names depend on structure
1) 3,4 - dimethyl -3- propyl nonane 3) Root word indicates functional group
2) 4-ethyl - 4,5 - di methyl decane 4) Sum of numbers indicating position of
3) 6,7 - dimethyl -7 ethyl nonane substituents must be maximum in IUPAC system.
4) 6,7 -dimethyl 1-7 - ethyl decane 16. Total number of chain isomers possible for C6
9. The IUPAC name of H14is
OH CH3 1) 2 2) 3 3) 4 4) 5
| | 17. Carboxlic acids are functional isomers of
CH3 -CH -CH2 _CH - CHOis 1) Alchols 2) Ethers
3) Esters 4) Amides
18. An isomer of ethanol is 31. The incorrect statement about homologous series is
1) methanol 2) diethyl ether 1) Consecutive members are differ by M.wt 14
3) acetone 4) dimethyl ether 2) All members of the series posses same general
19. The compound is not isomeric with diethyl ether molecular formula & functional group
is 3) They posses similar physical properties
1) n- propyl methylether 2) 1- butanol 4) The posses similar chemical properties
3) 2- methyl-2- propanol 4) butanone 32. The correct priority order of principal functional
20. Which class of compound can not show position group
isomerism? a) acids b) aldehydes
1) alkanes 2) Alkenes c) nitriles d) alcohols
3) Alkynes 4) Alcohols 1) a  b  c  d 2) a  c  d  b
21. The number of branched chain isomers of 3) a  c  b  d 4) a  d  b  a
molecular formula C6 H14 are
COMPREHENSION MODEL QUESTIONS
1) 5 2) 4 3) 3 4) 2
I. An organic compound contains 7C - atoms
22. isomerism exhibited by acetic acid and methyl
arranged horizontally in which two methyl groups
formate is
are at 2nd and 6th carbon atoms, there are two
1) functional 2) chain
double bonds between 2, 3 carbons and 5,6 carbons
3) geometrical 4) position
4th carbon is attached with oxygen through a
23. CH 3  NH  CH 2  CH 2  CH 3 and double bond then
33. IUPAC - name of the compound
CH 3  CH 2  NH  CH 2  CH 3 are 1) 1,1, 5, 5- tetramethyl pent - 1, 4- diene - 3- one
1) Chain isomers 2) Position isomers 2) 1, 1, 5 - trimethyl hex - 1, 4 - diene - 3- one
3) functional isomers 4) metamers 3) 2, 6 - dimethyl hept - 2, 5- diene - 4- one
24. Total number of alcohol isomers possible for the 4) Tetramethylheptaladiene
molecular formula C4 H10 O 34. The types of hybrid orbitals present in it are
1) 4 2) 3 3) 3 4) 1
1) sp 3 , sp 2) sp 2 , sp
25. Number of isomeric alcohols with formula C3 H8
O is 3) sp 3 , sp 2 4) sp 3 , sp 2 , sp
1) 1 2) 2 3) 3 4) 4
26. Ortho and meta dichloro benezene are examples 35. Number of '  ' and '  ' bonds present in it are
of 1) 23 & 2 2) 23 & 3
1) chain isomers 2) Position isomers 3) 20 & 5 4) 21 & 3
3) Functional isomers 4) Metemers 36. Number of sp 2  sp 2 overlappings present in it are
27 Total number of position isomers possible for the 1) 2 2) 3 3) 4 4) 1
formula C3 H5 Cl5
1) 1 2) 2 3) 4 4) 5 37. Number of primary , secondary and teritiory
28. n - propyl alcohol and isopropylalcohol are carbon atoms present in it are
1) Chain isomers 2) Position isomers 1) 2, 3, 4 2) 4, 3, 2
3) functional isomers 4) metamers 3) 3, 4, 2 4) 2, 4, 3
29. 2- methyl pentane & 3- methyl pentane are II. An aromatic carbocyclic compound consists of
1) Chain isomers 2) Position isomers Carbon, Hydrogen and Oxygen has a molecular
3) Functional isomers 4) Metamers weight of 108. In which Carbon and Hydrogen
30. The functional isomers of Butanoic acid atoms ratio 7 : 8 It shows functional isomerism
1) CH 3  COO  CH 2  CH 3 for alcohols and ethers
38. The number of possible isomers shown by it are
OH 1) 3 2) 4 3) 5 4) 6
|
39. Number of  and  bonds present in it are
2) CH 3  CH  CH 2  CHO
1) 12, 3 2) 16, 3 3) 14, 4 4) 15, 4
40. Total number of orbitals present in it are
O 1) 20 2) 18 3) 26 4) 32
||
3) 4) All
CH 3  C  CH 2  CH 2  OH
41. Number of 1o , 2o and 3o carbon atoms in etheric

form IIT JEE W orksheet
1) 1, 6, 0 2) 1, 2, 3 3) 2, 4, 0 4) 6, 0,1
1. The IUPAC name of the compound
o o
42. Number of 1 , 2 and 3 carbon atoms in
o
H
alcoholic form |
1) 2, 3, 2 2) 1, 5, 1 3) 3, 2, 2 4) 5, 1, 1 CH 3  C  CH 2 Br
|
III. An aliphatic organic compound has general CH3
formula Cn H 2 n  2O it shows chain isomerism with
1) 2- bromo propane
minimum number of carbon atoms and has a 2) 2- bromo , 2- methyl propane
molecular weight of 74. All carbons and oxygen 3) 1- bromo propane
shows same hybridisation 4) 1- bromo, 2- methyl propane
43. The no. of Isomeric alcohols and ethers shown by 2. Meleic and fumaric acids are a pair of ...isomers
it are 1) Postition 2) Cis - trans
1) 2, 3 2) 4, 3 3) 3, 4 4) 3, 2 3) Chain 4) functional
44. Number of primary and secondary alcohols shown 3. The number of  -bonds in the ethylene molecule
by it are is.....
1) 2, 3 2) 2, 2 3) 2, 1 4) 1, 2 1) 7 2) 5 3) 3 4) 2
45. The number of alcohols that does not contain
secondary carbon atoms 4. CH 3  CH 2  CH  CH 2  CH 2  CH 3
|
1) 1 2) 2 3) 3 4) 4 CH 3
46. IUPAC name of the ether containing isopropyl IUPAC name is

group 1) 3 - Methyl hexane 2) 4 - Methyl hexane
1) 1- Methoxy propane 3) iso - hexane 4) iso - pentane
2) 2- methoxy propane 5. The IUPAC name of the compound
3) Methyl, n- propyl ether
CH 3  CH 2  CH 3  C  CH 2 is
4) Methyl, isopropyl ether
Note: Use the following options to answer the Q.no. 1) 2 - Methyl - 1- butene
47 to 20 2) 1 - Methyl - 2- butene
1) Both A and R are false 3) iso butene
2) Both A and R are true and R is correct 4) iso - pentene
explantion of A 6. The IUPAC name for
3) Both Aand R are true but R is not correct CH 2  CH  CH 2  CH 3
explantion of A | |
4) A is true but R is false CH3 OH

47. Assertion (A) : The bond angle in CH4is the same 1) 3- Pentanol
as in the case of CC l 4 2) 1- Methyl - 2- butanol
Reason (R) : C-H bonds in the methane are almost 3) 2 - Hydroxy pentane
all nonpolar but C - C l Bonds in CC l 4 are 4) 3- Hexanol
7. An isomer of ethanol is
highlypolar
1) Methanol 2) Diethyl ether
48. Assertion (A) : Alkanes having more than three
3) Acetone 4) Dimethyl ether
carbon atoms exhibit chain isomerism
8. The number of structural isomers possible for
Reason (R) : All carbon atoms in akanes are of sp
hybridisation C3 H 5Cl3
49. Assertion (A) : Alkanes are quite inert 1) 4 2) 5 3) 7 4) 8
Reason (R) : Resonance stabilises the molecules 9. The number of isomeric structures possible for a
50. Assertion (A) : The structure of CH4 is tetrahedron
molecule having molecular formula C5 H12
Reason (R) : It has 4 bonds pairs in its valance
shell 1) 2 2) 3
3) 4 4) 5
10. The IUPAC name of the compound having the 21. The structural formula of 2- methyl - 2- butene
is......
formula CH  C  CH  CH 2 is
1) 1- butene 2- yne 2) 2- butene - 3- yne 1) CH 3  CH  CH 3   CH  CH 2
3) 1- butene - 3- yne 4) 2- butene - 1- yne
11. The hybridisation state of carbon atoms in the 2) CH 3  CH 2  C  CH 3   CH 2
product formed by the action of ethyl chloride with 3) CH 3  CH  CH  CH 3
aqueous KOH is
1) sp 2) sp 2 3) sp 3 4) sp 3 d 4) CH 3  CH  C  CH 3   CH 3
12. The alkane that yields two isomeric monobromo 22. Which one of the following pairs of compounds
derivatives are functional isomers?
1) Neopentane 2) Ethane 1) CH 3CH 2CH 2OH , CH 3CH  OH  CH 3
3) Methane 4) Propane
13. The IUPAC name of the compound having the 2) CH 3CH 2CH 2CH 2OH ,  CH 3 2 CHCH 2OH
formula  CH 3 3 C  CH  CH 2 is 3) CH 3CH 2CH 2OH , CH 3CH 2CH 2Cl
(EAMCET-1997)
1) 3, 3, 3- trimethyl, 1- propene 4) CH 3CH 2CH 2OH , CH 3  O  CH 2CH 3
2) 3, 3 - dimethyl, 1- butene 23. Which one of the following compound is an
3) 1, 1,1 - trimethyl, 3 - propene isomer of 1 - butanol?
4) 1, 1, - dimethyl, 3- butene 1) 2 - methyl - 2 - butanol
14. n - octane and n - nonane have 2) 2 - methyl - 1- butanol
1) same molecular formula 3) 3 - methyl - 2- butanol
2) same molecular weight 4) 2 - methyl - 1- propanol
3) similar chemical properties 24. 2,3-dimethyl hexane contains.. ... tertiary .....
4) same boiling point secondary and ....primary carbon atoms,
15. The trivial name of 4 - methyl aniline is respectively
1) p - toluedine 2) o - tuluedine 1) 2, 2, 4 2) 2, 4, 3 3) 4, 3, 2 4) 3, 2, 4
3) p-cresol 4) o - cresol 25. How many "methyl groups" are present in 2, 5 -
16. The hybridisation involved in acetylene is dimethyl-4-ethyl heptane?
1) 2 2) 3 3) 4 4) 5
1) sp 2) sp 2 3) sp 3 4) dsp 2
26. Match the following lists
17. The number of  - bonds in the product formed List -I List - II
by passing acetylene through dil H 2 SO4 A) Ethane 1) 2sp carbons
containing mercuric sulphate is B) Ethylene 2) 6sp 2 carbons
1) zero 2) one 3) two 4) three
18. Among the following compounds which have more C) Acetylene 3) 2sp 3 carbons
than one type of hybridization for carbon atoms? D) Benzene 4) 2sp 2 carbons
1) CH 3  CH 2  CH 2  CH 3
5) 1sp and 1sp 2 carbons
2) CH 3  CH  CH  CH 3 27. Match the following lists
List -I List - II
3) CH 2  CH 2 4) H  C  C  H
A) R  CHO 1) Aldehyde
19. The hybridisation involved in the six carbon
atoms of benzene is B) R  CO  R 2) Nitrile
1) Three sp 3 and three sp 2 C) R  CO2 H 3) Ketone
2) Three sp 2 and three sp 3 D) R  CN 4) Ester
5) Carboxylic acid
3) Three sp 2 and three sp 3
4) All six sp 2
20. The homologue of ethyne is
1) C2 H 4 2) C2 H 6 3) C3 H 8 4) C3 H 4

10. ORGANIC CHEMISTRY---XC

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10. ORGANIC CHEMISTRY---XC

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Learning Outcomes Organic Chemistry

By the end of this chapter, you will understand

and CO2 . heat

(linear chain) (branched chain) (Cyclic)

Carbon forms a number of compounds due C –– C 348

8. Statement I: The carbon present in organic

5. Organic chemistry deals with the study of: Example, X-M-X

(2) Closed-chain or Cyclic compounds :

Homocyclic compounds are further divided into two categories :

(ii) Aromatic heterocyclic compounds : Heterocyclic compounds which resemble aromatic

The classification may be summarised as follows :

Open – chain Closed – chain

Alicyclic Aromatic Alicyclic Aromatic

7. Classification of organic compounds based on type of bond present

Alkane Number of carbon atoms Formula (CnH 2n+2)

Alkane Number of carbon atoms Formula (CnH 2n+2)

Alkane Number of carbon atoms Formula (CnH 2n+2)

Alkane Formula (Cn H2n+2) Difference in formulae

Alkane Formula (Cn H2n+2) Difference in formulae

Alkane Formula (C nH2 n+2) Difference in formulae

Characteristics of a homologous series

c) Hetero cyclic compounds 3)

9. State of carbon in carbon compounds

sp3 – sp3 < sp2 – sp2 < sp – sp

d) HCHO, CH3CHO, C2H5OH

10. Classification of organic compounds based on type of functional

C H or C O The alkene group is a carbon-carbon double bond.

The ketone group consists of one carbon atom and

Carboxylic acids  COOH Carboxyl

Carbon chain Word root Carbon chain Word root

Functional group Sec.suffix Examples

Ketone ( CO) – one Propane – propanone (CH 3COCH3)

Substituent Secondary prefix Substituent Secondary prefix

Formula Cn (H2n+2) IUPAC name

Formula of IUPAC name Formula of

Classification of carbon and hydrogen in an organic compound

Types of alkyl groups

the other end with no other branching is said to be an isoalkyl group.

S.No Alkyl group Common name IUPAC name

5. CH3 C tert-butyl 1,1-Dimethylethyl

H3C CH CH2 C CH3

The type of carbons present are :

H) Secondary alkyl group l) H 3C C CH2

I) Tertiary alkyl group m) CH 3 CH 2 CH 2

N) Isoalkyl group n) CH3 C CH3

A) Neo alkyl group o) CH3 CH CH3

c) NH2 ,  Br,  CH3 ,  NO2 d) NH2  Cl ,  NO2 ,  CH3

Statement B : When hydrogen atom is removed

Formula Common name IUPAC name

CH  C  CH2  Propargyl Propynyl

12. Basic Rules of Nomenclature

given 4 and 5 and in the second way the numbers

4 - Ethyl - 3 - methyl octane

3 – Ethyl – 2, 2, 3, 5 – tetramethyl hexane 3, 3 – Diethyl – 2, 4, 7 – trimethyl octane

1. Carboxylic acid – COOH 7. Ketone CO

6. Nitrile – CN 12. Alkene C=C

C2H5 CH3 CH3CH2

vii) (CH3)3C – CH3

47. Give the IUPAC names of the following CH3

ii) CH3 – CH2CH2 – CH2 – CH – CH2 – CH2 – CH2 – CH2 – CH3