Organic

Chemistry
Organic chemicals appear in materials like clothing, fuels, polymers,
dyes and medicines.
It is about the compounds present in living organisms.

JI
They all contain carbon.
Organic Chemistry is the Chemistry of Carbon.

LA
In 1828, Wohler (a German chemist) synthesized an organic
compound, urea from an inorganic compound
A
B

(Inorganic compound) (Organic compound)

 Tetravalence Of Carbon
The shapes of molecules like
 Methane (CH4) – are explained in terms of the use of sp3
hybridisation
 Ethene (C2H4) - sp2 hybridisation carbon Ethene
 Ethyne (C2H2) - sp hybridisation carbon Ethyne
 JI
Complete Structural Formulas:

LA
A
B
Bond-line Structural Formulas:
In this bond-line structural representation of organic compounds,
carbon and hydrogen atoms are not shown and the lines representing
carbon-carbon bonds are drawn in a zig-zag fashion.
The terminals denote methyl (–𝐶𝐻3 )groups.
The line junctions denote carbon atoms bonded to appropriate number
of hydrogens required to satisfy the valencyof the carbon atoms.
3-Methyloctane can be represented in various forms as

JI
LA
A
B
3-D Representation of Organic Molecules
By using solid ( ) and dashed ( ) wedge formula, the 3-D image of
a molecule from a two-dimensional picture can be perceived.
The solid-wedge is used to indicate a bond projecting out of the plane of
paper, towards the observer.
The dashed-wedge is used to depict the bond projecting out of the plane
of the paper and away from the observer.
 Classification Of Organic
Compounds

JI
1.Basing on functional group
2.Basing on Carbon chain

LA
3.Homologous series
A
B
Acyclic Or Open Chain Compounds Cyclic Or Closed Chain Compounds

Homocyclic Compounds Heterocylic Compounds

Alicyclic Compounds Aromatic Compounds

Benzenoid Compounds Non-benzenoid Compound

Acyclic or Open Chain Compounds
These compounds are also called as aliphatic compounds and consist of
straight or branched chain compounds.

JI
Eg:

LA
A
B
Alicyclic or Closed Chain or Ring Compounds
Alicyclic (aliphatic cyclic) compounds contain carbon atoms joined in
the form of a ring.
If atoms other than carbon are present in the ring then they are called
Heterocylic compounds.
Aromatic compounds

Aromatic compounds are special types of compounds.

JI
These include benzene and other related ring compounds (benzenoid).
Like alicyclic compounds, aromatic compounds may also have hetero

LA
atom in the ring. Such compounds are called Hetrocyclic aromatic
compounds.
A
B
Benzenoid aromatic compounds

Non-benzenoid compound
Heterocyclic aromatic compounds

JI
LA
A
B
Functional group of a carbon atom is
defined as an atom, bond or group of
atoms in its molecule that
responsible for the characteristic
properties of the compound.
B
A
LA
JI
Homologous Series:

A homologous series is a series of compounds that have the same

functional group, and each member differs from the next member by a –
CH2 – unit in their formulae.

CH4 C2H6 C3H8 C4H10

CH2 CH2 CH2

E.g: alkanes: CnH2n+2 alkanols: CnH2n+1OH

alkenes: CnH2n alkanals: CnH2n+1CHO

alkynes: CnH2n-2 alkanoic acids: CnH2n+1COOH

Nomenclature Of Organic Compounds
The International Union of Pure and Applied Chemistry (IUPAC)

JI
developed a system for naming organic compounds.
This system eliminated many of the ambiguities that overwhelmed

LA
earlier naming systems
Common names for many substances are still widely used.
Eg: Buckminsterfullerene is a common name given to the newly
A
discovered C60 cluster.
B
A series of prefixes are used to designate the number of carbon atoms in
a carbon chain

meth 1C hex 6C

eth 2C hept 7C

prop 3C oct 8C

but 4C Non 9C

pent 5C Dec 10 C
Alkanes are named by a process that uses
Prefix - Parent - Suffix

JI
LA
branching groups
are in longest chain?
A
B
Straight chain alkanes are also called unbranched alkanes

Straight-chain alkanes have a zig-zag orientation when they are in their

most straight orientation
IUPAC Names of Some Unbranched Saturated Hydrocarbons

JI
LA
A
B
Branched alkanes have at least one carbon which is attached to more
than two other carbons
Nomenclature of Branched-Chain Alkanes:
Locate the longest continuous chain of carbons; this is the parent chain
and determines the parent name.

JI
LA
Number the longest chain. The numbering is done in such a way that
the branched carbon atoms get the lowest possible numbers.
A
The names of alkyl groups attached as a branch are then prefixed to
the name of the parent alkane and position of the substituents is
B
indicated by the appropriate numbers.
When two or more substituents are identical, use the prefixes di-, tri-,
tetra- etc.
When two chains of equal length compete to be parent, choose the
chain with the greatest number of substituents

When branching first occurs at an equal distance from either end of

the parent chain, choose the name that gives the lower number at the
first point of difference
Cyclic Compounds:

A saturated monocyclic compound is named by prefixing „cyclo‟ to the

corresponding straight chain alkane.

JI
Cycloalkanes generally are shown as skeletal structures.

LA
A
B
Various functional groups have unique suffixes that designate the
functional group.
The functional group takes precedence in numbering the carbon
chain.
Branches to the carbon chain are named in the usual manner.

alcohols “ol” Amides “amide”

Aldehydes “al” Amines “amine” or amino as a prefix
Ketones “one” Ethers Ethoxy as prefix
Acids “oic” halohydrocarbons Fluoro, bromo, chloro or iodo
Esters “oate”
B
A
LA
JI
Benzene is the parent name for some monosubstituted benzenes; the
substituent name is added as a prefix

For other monosubstituted benzenes, the presence of the substituent

results in a new parent name
When two substituents are present their position may be indicated by the
prefixes ortho, meta, and para (o, m and p) or by the corresponding
numerical positions

JI
LA
A
B
Dimethyl substituted benzenes are called xylenes
Numbers must be used as locants when more than two substituents are
present
The lowest possible set of numbers should be given to the substituents

JI
The substituents should be listed in alphabetical order
If one of the substituents defines a parent other than benzene, this

LA
substituent defines the parent name and should be designated position 1

A
B
The phenomenon of existence of two or more compounds possessing the
same molecular formula but different properties is known as isomerism.
Such compounds are called as isomers.
Two forms of isomerism

 Structural isomerism

 Stereoisomerism

Structural isomerism

 Same empirical formula but different atom-to-atom connections.

Stereo isomerism

 Same atom-to-atom connections but different arrangement in

space.
 JI
Chain
Isomerism

LA
Geometrical
Isomerism

Position
Isomerism
A
Optical
Isomerism
Functional
Group
B
Isomerism

Metamerism
 SCIENCE CLUB

PHYSICS#2.0

CHEMISTRY#2.0 3.0

BIOLOGY#2.0

MATHS#1.0

https://cbseacademic.nic.in/additionalPQ.html
 Chain isomerism:
When two or more compounds have similar molecular formula but
different carbon skeletons, these are referred to as chain isomers and

JI
the phenomenon is termed as chain isomerism.
Eg:

LA
A
B
 Position isomerism:
When two or more compounds differ in the position of substituent atom
or functional group on the carbon skeleton, they are called position
isomers and this phenomenon is termed as position isomerism.

Eg:
Functional group isomerism

Two or more compounds having the same molecular formula but

different functional groups are called functional isomers and this

JI
phenomenon is termed as functional group isomerism.

LA
A
B
 Metamerism:

It arises due to different alkyl chains on either side of the functional group
in the molecule.

Ethoxy ethane methoxypropane

Geometrical Isomerism

Compounds with same molecular formulae and have different

spatial arrangement exhibits geometrical isomerism.

JI
LA
A
B
E- Higher atomic number
elements on same side of
double bond.
Z- Higher atomic number
elements on opposite side
of double bond.

Cis- Higher atomic number

elements on same side of double
bond.
Trans- Higher atomic number
elements on opposite side of double
bond.
 Optical isomerism

 Molecules with non

superimposable mirror images

JI
are called chiral .

LA
 The non superimposable
mirror images and
stereoisomers are called
A
enantiomers.
B

 There are distinguished by

D,L configurations.
D,L – system of configuration

D refers to an arrangement
about a centre of chirality such
that OH on the right side of
Fischer‟s projection formula.

L refers to an arrangement
about a centre of chirality such
that OH on the left side of
Fischer‟s projection formula.
 Organic Reaction Mechanism
The general organic reaction is depicted as follows :

Organic Attacking reagent

JI
Molecule [Intermediate] Products
(Substrate) Byproducts

LA
A sequential account of each step, describing details of electron
movement, energetics during bond cleavage and bond formation, and the
A
rates of transformation of reactants into products is referred to as Reaction
Mechanism.
B
Fission of a Covalent Bond

A covalent bond can get cleaved by:

• Heterolytic cleavage
• Homolytic cleavage.
Homolytic Fission:
When the cleavage of covalent bond between two atoms enables each
atom to retain one electron of the shared pair instead of electron pair, it

JI
is known as homolytic fission.
The free radicals are denoted by dot over the symbol of atom or group

LA
of atoms.

. .
Eg: homolytic fission
A
A:B A + B
B

free radicals
Heterolytic fission:

Heterolytic fission is unsymmetrical wherein the bond breaks and

shared pair of electron remains with one of the fragments
This results into two charged particles as:

heterolytic fission B
A:B A +

Nucleophile, Nu Electrophile, E
Nucleophile, Nu-:
A reagent that brings an electron pair is called a nucleophile
Nucleophile or nucleus seeker or anion is a species that donate an

JI
electron pair to a positive ion.
All molecules or ions with a free pair of electrons or at least one pi

LA
bond can act as nucleophiles.
Because nucleophiles donate electrons, they are by definition Lewis
A
bases.
Eg: OH-, CN-, Cl-, Br-, I-, NO3-, SO42-, H2O, NH3 ………. etc.
B
Electrophile, E+:

A reagent that takes away an electron pair is called Electrophile.

Electrophiles or electrons seekers or cations are positively charged
species that accept electron pair.
Because electrophiles accept electrons, they are Lewis acids.
Most electrophiles are positively charged, have an atom that carries a
partial positive charge.
Eg: H+, NH4+, NO2+, SO3H+, RCO+, BF3, AlCl3, FeCl3 ……….. etc.
The movement of electrons in organic reactions can be shown by

from π bond to adjacent bond position

JI
from π bond to adjacent atom

LAfrom atom to adjacent bond position

A
Movement of single electron is indicated by a single barbed „fish hooks‟
B
The electron displacement in an organic molecule takes place either in
the ground state under the influence of an atom or a substituent group or
in the presence of an appropriate attacking reagent.
Inductive effect and resonance effects are examples of the electron
displacements.
The electron displacements due to the influence of an atom or a
substituent group present in the molecule cause permanent polarlisation
of the bond.
Temporary electron displacement effects are seen in a molecule when a
reagent approaches to attack it . This type of electron displacement is
called electromeric effect or polarisability effect.
1. Permanent effect in saturated carbon chain compounds.
2. Group attached to carbon chain should have tendency to
release or withdraw electrons.

JI
Types of inductive effect

LA
+ I Effect Effect – Electron Donating Groups
Eg: CH3 , C2 H5
A
– I Effect Effect – Electron Withdrawing Groups
Eg: - NO2 , –CN, - COOH
B
Temporary effect which is observed in presence of reagents involving
transfer of electrons of a shared pair of π-electrons to one of the atoms
joined by a multiple bond on the demand of an attacking reagent.
It is represented by E and the shifting of the electrons is shown by a
curved arrow ( ).
Positive Electromeric Effect (+E effect)

π−electrons of the multiple bond are transferred to that atom to which

the reagent gets attached.

JI
LA
Negative Electromeric Effect (-E effect)

π - electrons of the multiple bond are transferred to that atom to

A
which the attacking reagent does not get attached.
B
Structures I and II are equal resonance contributors to the real
structure of benzene
Benzene is particularly stable because it has two equivalent and
important resonance structures
Each carbon-carbon bond distance is 1.39 Å and a carbon-carbon
double bond distance is 1.33 Å
Often the hybrid is represented by a circle in a hexagon (III)
The resonance structures (canonical structures or contributing structures)
individually do not characterize any real molecule

Eg: Consider nitromethane(CH3NO2)

JI
LA
A
The two N–O bonds of nitromethane are of the same length (intermediate
B
between a N–O single bond and a N=O double bond). The actual structure
of nitromethane is therefore a resonance hybrid of the two canonical
forms I and II.
 The energy of actual structure of the molecule (the resonance hybrid) is
lower than that of any of the canonical structures.
The difference in energy between the actual structure and the lowest
energy resonance structure is called the Resonance stabilisation energy
or simply the resonance energy.

Rules for writing resonance structures:

The resonance structures have
• the same positions of nuclei
• the same number of unpaired electrons.
The polarity produced in the molecule by the interaction of two π-bonds
or between a π-bond and lone pair of electrons present on an adjacent
atom.

JI
Positive Resonance Effect (+R effect)

LA
The transfer of electrons is away from an atom or substituent group
attached to the conjugated system.
A
B
Negative Resonance Effect (- R effect)
The transfer of electrons is towards the atom or substituent group
attached to the conjugated system
Partial overlap of the s bonding orbital of an adjacent C-H bond with
the vacant 2p orbital of the cationic carbon delocalizes the positive

JI
charge and also the electrons of the adjacent s bond
Replacing a C-H bond with a C-C bond increases the possibility for

LA
hyper conjugation.

A
B
Substitution reactions
Addition reactions
Elimination reactions
Rearrangement reactions
The reaction in which hydrogen or any
atom or any functional group is substituted

JI
by another atom or group

LA
Eg:
A
B
The reaction in which the reagent and the
substrate combine together to give a single
product.

Eg:
The reaction in which two or more atom of
substrate are removed to form multiple

JI
bonds.

LA
Eg:
A
B
Molecules in the presence of reagents
undergoes rerrangement.

Eg:
Methods of Purification of Organic
Compounds
Sublimation

JI
Crystallisation
Distillation

LA
Differential extraction
Chromatography
A
B
 Filtration
It is used when only one of the compounds is soluble in the given solvent.
Eg: Urea and Naphthalene
Benzoic acid and anthracene
Used to separate volatile organic compounds from non volatile
impurities

JI
E.g. Naphthalene, benzoic acid, anthracene, camphor.

LA
A
B
 Crystallization
Most common method for purification of solid organic compounds.
Impurities and organic compound have different solubilities in the given
solvent.
The organic compound should be insoluble or sparingly soluble in the
solvent at room temperature but readily soluble at high temperature.
The impurities should be insoluble in the solvent even at high
temperature .
The solution is concentrated to get a nearly saturated solution. On
cooling the solution, pure compound crystallises out and is removed by
filtration.

The organic compound should not react with the solvent.

 Distillation
Simple distillation:
Liquids having different boiling points vaporise at different temperatures.
The vapours are cooled and the liquids so formed are collected

JI
separately.Difference in boiling points of compounds is more than 40ºC.

LA
Eg: Chloroform (B. P- 334K) and Aniline (B. P- 457K).

A
B
Fractional distillation: Used if the difference in boiling points of
compounds is less than 40ºc.
Eg: Acetone (B. P. 329K) and Methyl alcohol (B. P. 338k).
Vacuum distillation: Used for organic compounds which decompose at or
below their boiling points.
Eg: Glycerol.

JI
LA
A
B
Steam distillation: Used for organic compounds which are immiscible
with water and are steam volatile.
Eg: Aniline.
 Differential Extraction
Used to extract pure organic compounds from their aqueous solution by
shaking with organic solvent in which they are highly soluble.
The organic solvent and the aqueous solution should be immiscible with

JI
each other so that they form two distinct layers which can be separated by
separatory funnel.

LA
Eg. Benzoic acid from its aqueous solution using benzene.
A
B
 Chromatography
It is an important technique extensively used to separate mixtures into
their components, purify compounds and also to test the purity of
compounds
It is based on selective adsorption or partition between stationary and
mobile phase.

Classification of Chromatography:

Adsorption Chromatography
Partition Chromatography
 Adsorption Chromatography:
Principle: When a mobile phase is allowed to move over a stationary phase
(adsorbent), the components of the mixture move by varying distances

JI
over the stationary phase.

Types of chromatographic techniques based on the principle of differential

LA
adsorption are :
Column chromatography
A
Thin layer chromatography.
B
Column Chromatography
A liquid or a mixture of liquids is
allowed to flow down the column
slowly.
Depending upon the degree to
which the compounds are adsorbed,
complete separation takes place.
The most readily adsorbed
substances are retained near the top
and others come down to various
distances in the column
Thin layer Chromatography
It is based on adsorption, used for quantitative analysis.
It involves separation of substances of a mixture over a thin layer of

JI
an adsorbent coated on glass plate.

LA
A
B

Chromatogram Being Developed Developed chromatogram

Partition Chromatography
Partition chromatography is based on continuous differential
partitioning of components of a mixture between stationary and mobile
phases.
Paper Chromatography: Based on partition and used for quantitative
and qualitative analysis
 Qualitative Analysis of Organic Compounds

Carbon and hydrogen are detected by heating the organic compound

JI
with copper oxide
Carbon present in the compound is oxidised to carbon dioxide and

LA
hydrogen to water

C + 2CuO → 2Cu + CO2

2H + CuO → Cu + H2O
A
CO2+ Ca(OH)2 → CaCO3↓+ H2O
B
5H2O + CuSO4 → CuSO4.5H2O
White Blue
Nitrogen, sulphur, halogens and phosphorus present in an organic
compound are detected by “Lassaigne‟s test”

Detection of Nitrogen
Detection of Sulphur

The sodium fusion extract is acidified with acetic acid and lead acetate is
added to it. A black precipitate of lead sulphide indicates the presence of

JI
sulphur.

𝑆 −2 + 𝑃𝑏 +2 → 𝑃𝑏𝑆

LA
On treating sodium fusion extract with sodium nitroprusside, appearance
of a violet colour further indicates the presence of sulphur.
A
B
Detection of Halogens
The sodium fusion extract is acidified with nitric acid and then treated
with silver nitrate.

JI
A white precipitate, soluble in ammonium hydroxide shows the
presence of chlorine

LA
A yellowish precipitate, sparingly soluble in ammonium hydroxide
shows the presence of bromine
A yellow precipitate, insoluble in ammonium hydroxide shows the
A
presence of iodine.
B
𝑋 − + 𝐴𝑔+ → 𝐴𝑔𝑋
Detection of Phosphorus
The compound is heated with an oxidising agent like sodium peroxide.
The phosphorus present in the compound is oxidised to phosphate.

JI
The solution is boiled with nitric acid and then treated with ammonium
molybdate.

LA
A yellow colouration or precipitate indicates the presence of
phosphorus.

𝑁𝑎3 𝑃𝑂4 + 3𝐻𝑁𝑂3 → 𝐻3 𝑃𝑂4 + 3𝑁𝑎𝑁𝑂3

A
B
𝐻3 𝑃𝑂4 + 12(𝑁𝐻4 ) 2 𝑀𝑜𝑂4 + 21𝐻𝑁𝑂3 →
Ammonium
molybdate (𝑁𝐻4 ) 3 𝑃𝑂4 . 12𝑀𝑜𝑂3 + 21𝑁𝐻4 𝑁𝑂3 +12𝐻2 𝑂
Ammonium
phosphomolybdate
 Quantitative Analysis

A known mass of an organic compound is burnt in the presence of excess of

oxygen and copper(II) oxide. Carbon and hydrogen in the compound are oxidised

JI
to carbon dioxide and water respectively.

CxHy+ (x + y/4) O2 → x CO2+ (y/2) H2O

LA
A
B
Dumas Method:
• The nitrogen containing organic compound, when heated with copper oxide
in an atmosphere of carbon dioxide, yields free nitrogen in addition to
carbon dioxide and water.
CxHyNz+ (2x + y/2) CuO → x CO2+ y/2 H2O + z/2 N2+ (2x + y/2) Cu
Kjeldahl’s Method:

The compound containing nitrogen is heated with concentrated

sulphuric acid. Nitrogen in the compound gets converted to ammonium

JI
sulphate.
The resulting acid mixture is then heated with excess of sodium

LA
hydroxide. The liberated ammonia gas is absorbed in an excess of
standard solution of sulphuric acid.
A
2NaOH
Organic compound + H2SO4 → (NH4)2SO4 → Na2SO4 + 2NH3 +
2H2O
B
2NH3+ H2SO4 → (NH4)2SO4
 Halogens
Carius method:
An organic compound is heated with
fuming nitric acid in the presence of

JI
silver nitrate contained in a hard glass

LA
tube known as Carius tube in a furnace.
Carbon and hydrogen present in the
compound are oxidised to carbon dioxide
A
and water.
B
The halogen present forms the
corresponding silver halide (AgX). It is
filtered, washed, dried and weighed
Sulphur

A known mass of an organic compound is heated in a Carius tube with

sodium peroxide or fuming nitric acid.
Sulphur present in the compound is oxidised to sulphuric acid. It is
precipitated as barium sulphate by adding excess of barium chloride
solution in water.
The precipitate is filtered, washed, dried and weighed. The percentage of
sulphur can be calculated from the mass of barium sulphate.
Phosphorus

JI
LA
A
B
Oxygen
A definite mass of an organic compound is decomposed by heating in
a stream of nitrogen gas.
The mixture of gaseous products containing oxygen is passed over
red-hot coke when all the oxygen is converted to carbonmonoxide.
This mixture is passed through warm iodine pentoxide(𝐼2 𝑂5 ) when
carbon monoxide is oxidised to carbon dioxide producing iodine.

The percentage of oxygen can be derived from the amount of carbon

dioxide or iodine produced.