CHEMISTRY

Hydrocarbon-
Part-I

Phasor Academy Contact- 9137061453/7710882858

 Hydrocarbon Part-I
Index : Preparing your own list of Important/Difficult
Instruction to fill Questions

(A) Write down the Question Number you are unable to solve in column A below, by Pen.
(B) After discussing the Questions written in column A with faculties, strike off them in the
manner so that you can see at the time of Revision also, to solve these questions again.
(C) Write down the Question Number you feel are important or good in the column B.

COLUMN :A COLUMN :B
EXERCISE
NO. Questions I am unable
Good/Important questions
to solve in first attempt

1.

2.

3.
Advantages

1. It is advised to the students that they should prepare a question bank for the revision as it is
very difficult to solve all the questions at the time of revision.

2. Using above index you can prepare and maintain the questions for your revision.

Contents
Particular's Page No.
Exercise - 1 Objective Question 01 – 6

Exercise - 2 7– 10
Part (I) : Objective Question
Part (II) : Miscellaneous Question
Section (A) : Assertion / Reasoning
Section (B) : Match the column
Section (C) : One or more than one option correct

Exercise - 3
JEE Problems (Previous Years) 11– 12
Part (I) :
Part (II) : AIEEE Problems (Previous Years) )

Answer Key
12
SYLLABUS
Alkanes- Nomenclature, isomerism, conformations (ethane only), physical properties, chemical reactions including
free radical mechanism of halogenation, combustion and pyrolysis.
Alkanes-Nomenclature, structure of double bond (ethene), geometrical isomerism, physical properties, methods of
preparation: chemical reactions: addition of hydrogen, halogen, water, hydrogen halides (Markovnikov’s addition
and peroxide effect), ozonolysis, oxidation, mechanism of electrophilic addition.
Alkynes-Nomenclature, structure of triple bond (ethyne), physical properties, methods of preparation, chemical
reactions: acidic character of alkynes, addition reaction of- hydrogen, halogens, hydrogen halides and water.
 Hydrocarbon-Part-I

 Marked Questions may have for Revision Questions.

ONLY ONE OPTION CORRECT TYPE

Section (A) :Alkane
1. Which of the following alkanes has the lowest boiling point?
(1) n-Pentane (2) Isopentane (3) Neopentane (4) n-Hexane.

2. Which of the following alkanes has the lowest melting point ?

(1) n-Butane (2) n-Pentane (3) Propane (4) n-Hexane.

3. The maximum C—C bond length is in:

(1) C2H6 (2) C2H4 (3) C2H2 (4) C6H6

4. When cyclohexane is poured on water, it floats because :

(1) cyclohexane is in boat form (2) cyclohexane is in chair form
(3) cyclohexane is in crown form (4) cyclohexane is less denser than water

5. Marsh gas mainly contains:

(1) C2H2 (2) CH4 (3) H2S (4) CO

6. When water vapours are passed over aluminium carbide, we get:

(1) acetaldehyde (2) ethylene (3) methane (4) methyl alcohol

7. The complete combustion of CH4 gives :

(1) CO + H2 (2) CO + N2 (3) CO + N2O (4) CO2 + H2O

8. Action of heat on a mixture of sodium propionate and sodalime produces:

(1) methane (2) ethane (3) propane (4) ethylene

9. An unknown carboxylic acid salt on kolbe’s electrolysis form cyclobutane; the carboxylic acid can be:
(1) adipic acid (2) hexanoic acid (3) succinic acid (4) fumaric acid

10. 20 ml of methane are burnt with 50 ml of oxygen, the volume of the gas left after cooling to room
temperature will be
(1) 80 ml (2) 60 ml (3) 30 ml (4) 20 ml

11. What is the volume of oxygen required for the the complete combustion of 4 litre of ethane?
(1) 4 litre (2) 8 litre (3) 12 litre (4) 14 litre

12. The reactivity of hydrogen atoms attached to carbon atom in the halogenation of an alkane has the
order :
(1) tertiary > primary > secondary (2) secondary > primary > tertiary
(3) tertiary > secondary > primary (4) primary > secondary > tertiary

13. Halogenation of alkanes is an example of

(1) Free radical addition reaction (2) Free radical substitution reaction
(3) Nucleophilic substitution reaction (4) Nucleophilic addition reaction.

14. Which of the following cannot be considered as a step of mechanism in chain reaction of methane with
CI2?

(1) Cl2  CI · (2) CH4 + CI·  CH CI + H·

3

· ·
(3) CI + CH4  CH3 + HCI (4) CI· + CH ·  CH CI
3 3

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15. During chlorination of methane to methyl chloride, the propagation step is represented by
   
(1) CI — CI 
h
CI  CI (2) CH3  CI  CH3CI
   
(3) CH4 + CI  CH3 + HCl (4) CI  CI  CI — CI

16. The major product obtained in the reaction, :


Br2


hv

(1) (2) (3) (4)

17. lodination of an alkane is carried out in presence of

(1) Alcohol (2) P + I2 (3) HNO3 or HIO3 (4) A reducing agent

18. Only two isomeric monochloro derivatives are possible for :-

(1) n-Pentane (2) 2,4-Dimethyl pentane
(3) Toluene (4) 2,3-Dimethyl butane
19. Which of the followings will give same product on complete hydrogenation.

(1) 1, 2, 3, 4 (2) 1, 3, 4 (3) 1, 2, 4 (4) 1, 2, 3

20. Number of moles of hydrogen required for complete hydrogenation of one mole of the following
compound :

(1) 6 (2) 7 (3) 5 (4) 3

Section (B) : Alkene

1. Ethylene readily undergoes:
(1) addition reaction (2) substitution reaction (3) elimination reaction (4) rearrangement reaction
2. Reaction of ethene with Br2 in CCI4 gives:
(1) Bromoethane (2) 1, 2-Dibromoethane
(3) 1, 1-Dibromoethane (4) 1, 1, 2, 2-Tetrabromoethane.

3. P (major), P is :

CH2—CH—CH3 CH—CH2CH3
(1) (2)
OH OH

CH CH—CH3
(3) (4) HO CH CH—CH3
OH

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4. Addition of HCI to 2-methyl-2-butene mainly gives

(1) 1-Chloro-2-methylbutane (2) 2-Chloro-2-methylbutane
(3) 2-Chlorobutane (4) 1-Chlorobutane.

5. Kharasch effect regarding addition of HBr is not observed in :

(1) hex–1–ene (2) prop–1–ene (3) hex–3–ene (4) pent–1–ene

6. Intermediate in the following reaction is

CH3–CH=CH2

(1) (2) (3) (4)

7. Peroxide effect is observed

(1) Only with HBr (2) Only with HI (3) Only with HCI (4) Only with HF

8. Reaction of HBr with propene in the presence of peroxide gives:

(1) isopropyl bromide (2) allyl bromide (3) n-propyl bromide (4) 3-bromopropane

9. Only two isomeric monochloro derivatives are possible for :-

(1) n-Pentane (2) 2,4-Dimethyl pentane
(3) Toluene (4) 2,3-Dimethyl butane

10. The number of possible monochloro derivatives of 2, 2, 3, 3-Tetramethylbutane is -

(1) 2 (2) 3 (3) 4 (4) 1

11. Which of the following alkene gives four monochloro (structural isomer) products after hydrogenation ?
(1) Pent-2-ene (2) 2-Methylbut-2-ene (3) 3-Methylhex-2-ene (4) 2, 3-Dimethylbut-2-ene

12. An organic compound C4H6 on ozonolysis gives formaldehyde and glyoxal. What is the structure of
organic compound ?

(1) (2) (3) (4) CH3–CH2–CCH

13. X 
O3 / Zn
 +

Y.
The IUPAC name of compound Y is :
(1) 2-Cyclohexyl butane (2) 1-Methyl propyl cyclohexane
(3) Butyl cyclohexane (4) 1-Cyclohexyl butane

14. An alkene give two moles of HCHO, one mole of CO2 and one mole of on

ozonolysis. What is its structure?

(1) (2)

(3) (4)

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Section (C) :Alkyne

1. General fomula CnH2n–2 represents:
(1) alkenes (2) alkanes (3) alkynes (4) none

2. To prepare But-2-yne from 2, 2, 3, 3-Tetrachlorobutane, reagent used is :

(1) Zinc dust /  (2) Sodamide (3) Alc. KOH (4) aq. KOH

3. Which of the following compounds on hydrolysis gives propyne ?

(1) CaC2 (2) Mg2C3 (3) Al4C3 (4) Cu2Cl2

4. Which of the following will react most readily with bromine?
(1) CH  CH (2) CH2 = CH2 (3) CH3CH = CH2 (4) CH3CH2CH3.

5. Most Acidic hydrogen is present in:

(1) ethyne (2) ethene (3) benzene (4) ethane

6. When 1-butyne is treated with excess of HBr, the expected product is

(1) 1, 2-Dibromobutane (2) 2, 2-Dibromobutane (3) 1, 1-Dibromobutane (4) All the above

7. Acetylene on treatment with dil. H2SO4 having HgSO4 gives :

(1) acetaldehyde (2) acetic acid (3) ethanol (4) ethylene

8. Which of the following reagents will distinguish between 1-butyne and 2-butyne?
(1) Br2/ CCI4 (2) AgNO3 + NH4OH (3) Dil. Cold KMnO4 (4) KMnO4

9. Ammonical AgNO3 give white ppt. after reaction with any compound then this reflects the presence of
(1) One – CHO group (2) One triple bond
(3) A terminal alkyne (4) Compound is unsaturated

10. Which will undergo reaction with ammonical AgNO3 :

(1) (2) CH3–CH=CH–CCH

(3) CH3–CH2–CH=CH–CH2–CH3 (4) CH2=CH–CH2–CH3

Section (D) :Miscellaneous Questions

1. Isomerization of an alkane may be carried out by using
(1) AI2O3 (2) HI/P
(3) Anhyd. AICI3 at 300ºC in presence of HCl (4) Conc. H2SO4.

2. Converting n-hexane into benzene in the presence of chromium oxide on alumina supports an example
of a
(1) Hydrogenation reaction (2) Isomerisation reaction
(3) Aromatization reaction (4) Substitution reaction.

3. The gas, which is used for artificial ripening of fruits, is:

(1) CH4 (2) C2H4 (3) C2H6 (4) none

Section (E) : Aromaticity

1. Which of the following statements is not correct ?
(1) An aromatic molecule must be cyclic
(2) An aromatic ring must be planar
(3) An aromatic ring must involve cyclic delocalization of (4n + 2) -electrons
(4) An aromatic ring must involve cyclic delocalization of 4n -electrons.

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 Hydrocarbon-Part-I

2. The general formula of arenes is :

(1) CnH2n (2) CnH2n–4 (3) CnH2n+2 (4) CnH2n–6

3. Number of  electrons in are :

(1) 2 (2) 4 (3) 5 (4) 6

4. Identify the aromatic compound ?

(1) (2) (3) (4)

5. Which of the following is not an aromatic compound:

(1) (2) (3) (4)

6. Among the following the anti aromatic speceis is :

(1) (2) (3) (4)

7. Which of the following compound is an Aromatic in nature.

O ..
O
..
–
(1) (2) (3) (4)

8. Which of the following ion is nonaromatic in nature.

+ – + –
(1) (2) (3) (4)

9. Which of the following molecules have all C–C bonds are of equal length?

–
(1) (2) (3) (4) All of these

10. In the compound C6H5Z which of the following set of groups is predominatly ortho/para directing ?
(1) Z = – NO2, — Cl, — OH (2) Z = – OMe, — CN, — NH2
(3) Z = – NHCOCH3, — Cl, — COOH (4) Z = – NHCOCH3, — CH3, — OH

11. Number of  electrons in conjugation for these compounds

, , and will be respectively :

(1) 8, 6, 6, 6 (2) 6, 4, 6, 6 (3) 6, 6, 6, 6 (4) 6, 6, 8, 6

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 Hydrocarbon-Part-I

Section (F) : Electrophilic substitution

1. The characteristic reaction of benzene is :
(1) Electrophilic addition (2) Nucleophilic substitution
(3) Electrophilic substitution (4) Nucleophilic addition.

2. Which of the following compounds reacts slower than benzene in electrophilic bromination ?
(1) C6H5CH3 (2) C6H5OH (3) C6H5NO2 (4) C6H5NH2

3. The decreasing order of reactivity towards electrophilic substitution reaction of the following compounds
is :
(i) benzene, (ii) chlorobenzene, (iii) nitrobenzene, (iv) toluene
(1) i > iii > iv > ii (2) iv > i > iii > ii (3) iv > i > ii > iii (4) iv > ii > i > iii

4. -NH2 group in aniline is :

(1) m-directing and deactivating (2) o, p-directing and deactivating
(3) o, p-directing and activating (4) m-directing and activating

5. Among the following groups, the group that deactivates the benzene ring for further electrophilic
substitution is:
(1) methyl (2) amino (3) hydroxyl (4) nitro

6. o,p-directing group are mostly :

(1) activating group (2) deactivating groups (3) neutral groups (4) none of these

7. The major product obtained in the following is :


Br2 /Fe


(1) (2)

(3) (4)

8. The compound X in the reaction,

+ ICl 
anhydrous AlCl3
 X

(1) (2) (3) (4)

9. Benzene when heated with conc. H2SO4 forms:

(1) benzene sulphate (2) benzene sulphite
(3) benzene hydrogen sulphate (4) benzene sulphonic acid

10. Benzene reacts with acetyl chloride in presence of anhydrous aluminium chloride to form:
(1) acetophenone (2) phenyl acetate (3) chlorobenzene (4) benzoic acid

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 Hydrocarbon-Part-I

 Marked Questions may have for Revision Questions.

1. Which of the following alkanes can be synthesized by the Wurtz reaction in good yield ?
(1) (CH3)2CH – CH2 – CH (CH3)2 (2) (CH3)2CH – CH2 – CH2 – CH (CH3)2
(3) CH3 – CH2 – C(CH3)2CH2 – CH3 (4) (CH3)3C – CH2 – CH2 – CH3

2. The product formed in the reaction

is
(1) (BrCH2)3CCH2CH2C(CH2Br)3 (2)

(3) (4)

3. Arrange-the following alkenes in decreasing order of reactivity towards electrophilic addition :
(i) (ii) CH3–CH=CH2 (iii) CH2=CH–Cl (iv) CH2=CH–CH2–Cl

(1) i > ii > iv > iii (2) i > iv > ii > iii (3) iv > i > ii > iii (4) iii > ii > i > iv

4. Which of the following compounds on hydrolysis gives acetylene ?

(1) CaC2 (2) Mg2C3 (3) Al4C3 (4) Cu2Cl2

5. Acetylene may be prepared by electrolysis of

(1) potassium oxalate (2) potassium acetate
(3) potassium maleate (4) potassium succinate

6. ...................... is obtained when iodoform is heated with Ag powder :

(1) CH4 (2) C2H4 (3) C2H6 (4) C2H2

7. 
HOBr (excess)

O O Br
|| ||
C C CH
(1) CHBr2 (2) CH2Br (3) (4) CHO

8. Compound 'A' gives red precipitate with Cu2Cl2 / NH4OH solution and decolourises bromine water. The
compound 'A' can be :
CH2  CH  C  CH3 CH2  CH  C  H
(1) || (2) || (3) CH3 – C  CH (4) PhCHO
O O

9. Identify the odd species out (which of the species among the following is different from others)?

(1) (2) (3) (4)

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Hydrocarbon-Part-I

10. Among following statements on the nitration of aromatic compounds, the false one is
(1) The rate of nitration of benzene is almost the same as that of hexadeuterobenzene
(2) The rate of nitration of toluene is greater than that of benzene
(3) The rate of nitration of benzene is greater than that of hexadeuterobenzene
(4) Nitration is an electrophilic substitution reaction.

11. Which of the following will undergo sulphonation at fastest rate ?

(1) (2) (3) (4)

12. Product is :

(1) (2) (3) (4) None of these

13. The organic products (X) formed in the following reaction is

C6H5CH2Cl + C6H6 
AlCl3
X

(1) (2) (3) (4)

14. The reaction least likely to occur is:

HNO3  H2SO4
(1)   (2) + H2SO4 
Heat


(3) + Cl2 

UV
 (4) + Br2 
Fe

15. Which of the following reactions is not an example of electrophilic substitution:


(1) C6H6 + NO2  C6H5NO2 (2) C6H6 + CH3Cl 
AlCl3
 C6H5 – CH3 + HCl

(4) C6H6+ CO + HCl  

anhydrous
(3) C6H6 + Cl2 
UV light
 C6H6Cl6 AlCl 3

16. Quinine is the most important alkaloid obtained from Cinchona bark. It’s molecular formula is
C20H24N2O2. It may contain
(1) 5 double bond & 6 ring (2) 6 double bond & 4 ring
(3) 6 double bond & 3 ring (4) 7 double bond & 5 ring

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 Hydrocarbon-Part-I

17. 
H2 /Ni
 Q

Which of the following is the correct statement about P & Q.

(1) Product will be 1-Methyl-3-(2-methylpropyl)cyclohexane.
(2) Product will be 3-Methyl-1-(2-methylpropyl)cyclohexane.
(3) DU of reactant P is 3.
(4) DU of product Q is zero.

18. Which alkyne will give 3-ethyl heptane on catalytic hydrogenation.

(1) (2) (3) (4)

19. If 1 mole H2 is reacted with 1 mole of the following compound.

Which double bond will be hydrogenated ?

(1) c (2) b (3) a (4) d

20. Identify E in the following sequence of reaction.

H / Ni
E (C6H10) 
2

 F (C6H12) G (C6H11Cl) (only one isomer)

(1) (2) (3) (4)

21. An unknown compound on ozonolysis to give acid C 3H6O2 and a ketone C4H8O. From this information,
identify structure of unknown compound.
CH3

(1) (CH3)2C= CHCH2 – CH2CH3 (2) CH3CH2 – C = CHCH2CH3

(3) (CH3)2CHCH= CHCH2CH3 (4) CH3CH2CH2CH = CHCH2CH3

22. Identify the structure of compound which consume only one mole H 2 gas during hydrogenation and give
only 2-monochloro structural products after hydrogenation. It yield only ketone after reductive
ozonolysis.

(1) (2) (3) (4)

23. An alkane with the molecular formula C7H16 forms seven monochlorinated products. The name of the
alkane is :
(1) Heptane (2) 2-Methylhexane
(3) 3-Methylhexane (4) 2,3-Dimethylpentane

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24. For the following reactions sequence

OHC CHO
O3
Zn/H2O
The structures of X and Y are :

(1) (2)

(3) (4)

O O O
|| || ||
25. X 
 H – C – CH2 – C – CH2 – C – H + HCHO
O3 / Zn, H2O

The structure of X will be :

(1) (2) (3) (4)

NEET / AIPMT QUESTION (PREVIOUS YEARS)

1. Among the following alkenes, [AIPMT 2000]
1-butene cis-2-butene trans-2-butene
I II III
the decreasing order of stability is :
(1) II > I > III (2) III > II > I (3) III > I > II (4) I > II > III

2. Propan–1–ol may be prepared by reaction of propene with [AIPMT 2000]

O
||
(1) CH3  C  O  O  H (2) H3BO3 (3) B2H6/NaOH-H2O2 (4) H2SO4/H2O

3. An organic compound A(C4H9Cl) on reaction with Na/diethyl ether gives a hydrocarbon which on
monochlorination gives only one chloro derivative, then A is [AIPMT 2001]
(1) t-butyl chloride (2) s-butyl chloride (3) iso-butyl chloride (4) n-butyl chloride

4. When CH3CH2CHCl2 is treated with NaNH2, the product formed is [AIPMT 2002]

(1) CH3–CH=CH2 (2) CH3–CCH (3) CH3CH2CH (4) CH3CH2CH

5. Reaction of HBr with propene in the presence of peroxide gives : [AIPMT 2004]
(1) Isopropyl bromide (2) 3-bromo propane (3) Allyl bromide (4) n-propyl bromide

6. The molecular formula of diphenyl methane, CH2 , is C13H12. [AIPMT-2004]

How many structural isomers are possible when one of the hydrogen is replaced by chlorine atom 
(1) 4  (2) 8 (3) 7  (4) 6

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 Hydrocarbon-Part-I

7. Using anhydrous AlCl3 as catalyst, which one of the following reaction produce ethylbenzene (PhEt)?
[AIPMT 2004]
(1) H3C – CH2OH + C6H6 (2) CH3 – CH == CH2 + C6H6
(3) C2H5Cl + C6H6 (4) H3C – CH3 + C6H6

8. The homologue of ethyne is : [AIPMT 2008]

(1) C2H2 (2) C2H6 (3) C3H8 (4) C3H4

9. Benzene reacts with CH3Cl in the presence of anhydrous AlCl3 to form : [AIPMT 2009]
(1) Toluene (2) Chlorobenzene (3) Benzylchloride (4) Xylene

10. Which of the following species is not electrophilic in nature? [AIPMT 2010]
  
(1) Cl (2) BH3 (3) H3 O (4) NO2

11. Which one of the following is most reactive towards electrophilic reagent ? [AIPMT 2011 Scr.]
CH3 CH3 CH3 CH3
(1) (2) (3) (4)
OCH3 OH NHCOCH3 CH2OH

12. Among the following compounds the one that is most reactive towards electrophilic nitration is :
[AIPMT 2012]
(1) Benzoic Acid (2) Nitrobenzene (3) Toluene (4) Benzene

13. Some meta - directing substituents in aromatic substitution are given. Which one is most deactivating ?
[NEET 2013]
(1) –SO3H (2) –COOH (3) –NO2 (4) –CN

14. Which of the following compounds will not undergo Friedal-Craft’s reaction easily : [NEET 2013]
(1) Xylene (2) Nitrobenzene (3) Toluene (4) Cumene

15. The radical, is aromatic because it has : [NEET 2013]

(1) 7 p-orbitals and 6 unpaired electrons (2) 7 p-orbitals and 7 unpaired electrons
(3) 6 p-orbitals and 7 unpaired electrons (4) 6 p-orbitals and 6 unpaired electrons

16. Which of the following organic compounds has same hybridization as its combustion product –(CO2) ?
[AIPMT 2014]
(1) Ethane (2) Ethyne (3) Ethene (4) Ethanol

17. In the following reaction [NEET-2-2019]

H3C–CCH 
A
RedHot IronTube
873K

number of () bond present in product (A) is -

(1) 21 (2) 9 (3) 24 (4) 18

18. The alkane that gives only one monochloro product on chlorination with Cl 2 in precence of diffused
sunlight is - [NEET-2-2019]
(1) 2,2,-dimethylbutane (2) neopentane
(3) n-pentane (4) Isopentane

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 Hydrocarbon-Part-I

EXERCISE - 1
SECTION (A)

1. (3) 2. (3) 3. (1) 4. (4) 5. (2) 6. (3) 7. (4)

8. (2) 9. (1) 10. (3) 11. (4) 12. (3) 13. (2) 14. (2)

15. (3) 16. (3) 17. (3) 18. (4) 19. (3) 20. (3)

SECTION (B)

1. (1) 2. (2) 3. (2) 4. (2) 5. (3) 6. (1) 7. (1)

8. (3) 9. (4) 10. (4) 11. (2) 12. (3) 13. (2) 14. (2)

SECTION (C)

1. (3) 2. (1) 3. (2) 4. (3) 5. (1) 6. (2) 7. (1)

8. (2) 9. (3) 10. (2)

SECTION (D)

1. (3) 2. (3) 3. (2)

SECTION (E)

1. (4) 2. (4) 3. (4) 4. (2) 5. (2) 6. (2) 7. (4)

8. (4) 9. (4) 10. (4) 11. (3)

SECTION (F)

1. (3) 2. (3) 3. (3) 4. (3) 5. (4) 6. (1) 7. (2)

8. (2) 9. (4) 10. (1)

EXERCISE - 2
1. (2) 2. (4) 3. (1) 4. (1) 5. (3) 6. (4) 7. (1)

8. (3) 9. (2) 10. (3) 11. (2) 12. (1) 13. (2) 14. (3)

15. (3) 16. (2) 17. (1) 18. (2) 19. (4) 20. (1) 21. (2)

22. (1) 23. (3) 24. (4) 25. (2)

EXERCISE - 3
1. (2) 2. (3) 3. (1) 4. (2) 5. (4) 6. (1) 7. (3)

8. (4) 9. (1) 10. (3) 11. (2) 12. (3) 13. (3) 14. (2)

15. (2) 16. (2) 17. (1) 18. (2)

PHASOR ACADEMY 7710882858 Page No:12