Chapter 21

Hydrocarbons

Only One Option Correct Type Questions

1. The reagent(s) for the following conversion.

?
Br H H
Br
is/are [IIT-JEE-2007 (Paper-1)]
(A) Alcoholic KOH (B) Alcoholic KOH followed by NaNH2
(C) Aqueous KOH followed by NaNH2 (D) Zn/CH3OH

2. The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an alkyne.
The bromoalkane and alkyne respectively are [IIT-JEE-2010 (Paper-1)]

(A) BrCH2CH2CH2CH2CH3 and CH3CH2C  CH (B) BrCH2CH2CH3 and CH3CH2CH2C  CH

(C) BrCH2CH2CH2CH2CH3 and CH3C  CH (D) BrCH2CH2CH2CH3 and CH3CH2C  CH

3. The compounds P, Q and S

O
COOH OCH3
C
O
HO H3C
P Q S
were separately subjected to nitration using HNO3/H2SO4 mixture. The major product formed in each case
respectively, is [IIT-JEE-2010 (Paper-2)]

COOH OCH3 C
O
(A)
HO H3C O2N
NO2 NO2

COOH OCH3 C
O
(B)
HO NO2 H3C NO2
NO2

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O NO2

COOH OCH3 C
O
(C)
HO H3C NO2
NO2
O

COOH OCH3 C
O NO2
(D)
HO H3C NO2
NO2
4. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) [IIT-JEE-2012 (Paper-1)]
(A) sp and sp3 (B) sp and sp2
(C) Only sp2 (D) sp2 and sp3
5. The number of optically active products obtained from the complete ozonolysis of the given compound is
[IIT-JEE-2012 (Paper-1)]

CH3 H
CH3 – CH = CH – C – CH = CH – C – CH = CH – CH3

H CH3

(A) 0 (B) 1
(C) 2 (D) 4
6. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the figure.

and and
I. II.

III.

The correct order of their boiling point is [JEE (Adv)-2014 (Paper-2)]

(A) I > II > III (B) III > II > I
(C) II > III > I (D) III > I > II
7. The major product formed in the following reaction is [JEE (Adv)-2021 (Paper-1)]

NaNH 2
Na
liq. NH3

(A) (B)

(C) (D)

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One or More Option(s) Correct Type Questions

8. In the Newman projection for 2, 2-dimethylbutane
X
H3C CH3

H H
Y
X and Y can respectively be [IIT-JEE-2010 (Paper-1)]
(A) H and H (B) H and C2H5
(C) C2H5 and H (D) CH3 and CH3
9. In the following reaction, the major product is [JEE (Adv)-2015 (Paper-1)]
CH3
CH2
1 equivalent HBr
H2C

CH3 CH3
CH3
(A) H2C (B)
H3C
Br Br

CH3 CH3
(C) (D)
H2C Br H3C Br

10. Among the following, reactions(s) which gives (give) tert-butyl benzene as the major product is(are)
[JEE (Adv)-2016 (Paper-2)]

Br
Cl
(A) (B)
NaOC2H5 AlCl3

OH
(C) (D)
H2SO4 BF3OEt2

11. The correct statement(s) for the following addition reactions is(are) [JEE (Adv)-2017 (Paper-1)]
H3C H
Br2/CHCl3
(i) M and N
H CH3

H3C CH3
Br2/CHCl3
(ii) O and P
H H
(A) O and P are identical molecules
(B) Bromination proceeds through trans-addition in both the reactions

(C) (M and O) and (N and P) are two pairs of enantiomers

(D) (M and O) and (N and P) are two pairs of diastereomers

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12. Choose the correct option(s) that give(s) an aromatic compound as the major product.
[JEE (Adv)-2019 (Paper-2)]

Br
(A) NaOEt

i) alc. KOH
H3C ii) NaNH 2
(B) Br
iii) red hot iron tube, 873 K
Br

UV, 500 K
(C) + Cl2(excess)

NaOMe
(D)

13. Which of the following reactions produce(s) propane as a major product? [JEE (Adv)-2019 (Paper-2)]
Br
(A) H3C Br Zn (B) H3C NaOH, CaO, 
COONa

(C) H3C Cl Zn, dil. HCl (D) H3C electrolysis

COONa + H2 O

14. Consider the following transformations of a compound P. [JEE (Adv)-2020 (Paper-2)]

(i) NaNH2 (i) X (reagent)

R P Q
(Optically active) (ii) C6 H 5COCH 3 ( C 9H 1 2) (ii) KMnO 4/H 2SO 4/  ( C 8H 12O 6)
+
(iii) H3 O /  (Optically active acid)
Pt/H 2

CH 3

Choose the correct option(s).

(A) P is (B) X is Pd-C/quinoline/H2

(C) P is (D) R is

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Linked Comprehension Type Questions

Paragraph for Q.Nos. 15 and 16

An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the
following sequence of ractions, in which Q is an intermediate organic compound.

(i) dil. H2SO4 / HgSO4

P Q
(C6H10) (ii) NaBH4 /ethanol
(iii) dil. acid (i) conc. H2SO4
(catalytic amount)
(–H2 O)
(ii) O3
(iii) Zn /H2O

O
2 C
H3C CH3 [IIT-JEE-2011 (Paper-1)]

Choose the correct answer :

15. The structure of compound P is

(A) CH3CH2CH2CH2 – C  C – H (B) H3CH2C – C  C – CH2CH3

H3C H3C
(C) H – C – C  C – CH3 (D) H3C – C – C  C – H
H3C H3C

16. The structure of the compound Q is

H3C OH H3C OH
(A) H – C – C – CH2CH3 (B) H3C – C – C – CH3
H3C H H3C H
H3C OH OH
(C) H – C – CH2CHCH3 (D) CH3CH 2CH 2CHCH 2CH 3
H3C

Paragraph for Q.Nos. 17 and 18

Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major products formed
in each step for both the schemes. [JEE (Adv)-2014 (Paper-2)]
1. NaNH2 (excess)
2. CH3CH2I (1 equivalent)
H X Scheme-1
3. CH3I (1 equivalent)
HO
M 4. H2, Lindlar’s catalyst

1. NaNH2 (2 equivalent)
OH
2.
Br
H Y Scheme-2
3. H3O , (mild)
N 4. H2, Pd/C
5. CrO3
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Choose the correct answer :

17. The product X is

H3CO H

(A) (B) H

H H H3CO

CH3CH2O H

H
(C) (D)
H H CH3CH2O

18. The correct statement with respect to product Y is

(A) It gives a positive Tollens test and is a functional isomer of X
(B) It gives a positive Tollens test and is a geometrical isomer of X
(C) It gives a positive iodoform test and is a functional isomer of X
(D) It gives a positive iodoform test and is a geometrical isomer of X

Paragraph for Q.Nos. 19 and 20

In the following reactions

Pd-BaSO4 i. B2H6
C8H6 C8H8 X
H2 ii. H2O2, NaOH, H2O
H2O
HgSO4, H2SO4
i. EtMgBr, H2O
C8H8O Y
+
ii. H , heat [JEE (Adv)-2015 (Paper-2)]

Choose the correct answer :

19. Compound X is

O OH

CH3 CH3
(A) (B)

OH
CHO
(C) (D)

20. The major compound Y is

CH3 CH3
(A) (B)

CH3
CH2
CH3 CH3
(C) (D)

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Paragraph for Q.Nos. 21 to 22

The amount of energy required to break a bond is same as the amount of energy released when the same bond
is formed. In gaseous state, the energy required for homolytic cleavage of a bond is called Bond Dissociation Energy
(BDE) or Bond Strength. BDE is affected by s-character of the bond and the stability of the radicals formed. Shorter
bonds are typically stronger bonds. BDEs for some bonds are given below: [JEE (Adv)-2021 (Paper-2)]

H3C(g) + H(g) H° = 105 kcal mol

–1
H 3C – H(g)

Cl(g) + Cl(g) H° = 58 kcal mol

–1
Cl – Cl(g)

H 3C – Cl(g) H3C(g) + Cl(g) H° = 85 kcal mol–1

H(g) + Cl(g)  H° = 103 kcal mol

–1
H – Cl(g)
Choose the correct answer :
21. Correct match of the C-H bonds (shown in bold) in Column J with their BDE in Column K is
Column J Column K
Molecule BDE (kcal mol–1)
(P) H-CH(CH3)2 (i) 132
(Q) H-CH2Ph (ii) 110
(R) H-CH=CH2 (iii) 95
(S) H-CCH (iv) 88
(A) P – iii, Q – iv, R – ii, S – i
(B) P – i, Q – ii, R – iii, S – iv
(C) P – iii, Q – ii, R – i, S – iv
(D) P – ii, Q – i, R – iv, S – iii
22. For the following reaction

light
CH4 (g)  Cl2 (g)  CH3 Cl(g)  HCl(g)

the correct statement is

(A) Initiation step is exothermic with H° = –58 kcal mol–1
(B) Propagation step involving CH3 formation is exothermic with H° = –2 kcal mol–1
(C) Propagation step involving CH3Cl formation is endothermic with H° = +27 kcal mol–1
(D) The reaction is exothermic with H° = –25 kcal mol–1
Matrix-Match / Matrix Based Type Questions
23. Match the chemical conversions in List I with the appropriate reagents in List II and select the correct answer
using the code given below the lists : [JEE (Adv)-2013 (Paper-2)]
List I List II

P. Cl 1. (i) Hg(OAc)2; (ii) NaBH4

Q. ONa OEt 2. NaOEt

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OH
R. 3. Et-Br

S. 4. (i) BH3; (ii) H2O2/NaOH

OH

Codes :
P Q R S
(A) 2 3 1 4
(B) 3 2 1 4
(C) 2 3 4 1
(D) 3 2 4 1
Integer / Numerical Value Type Questions
24. The number of hydroxyl group(s) in Q is [JEE (Adv)-2015 (Paper-2)]

H 
H 
aqueous dilute KMnO4 (excess)
 P  Q
heat 0 C

HO
H3C CH3

25. Total number of hydroxyl groups present in a molecule of the major product P is ____ [JEE (Adv)-2019 (Paper-2)]

(i) H2, Pd-BaSO4, quinoline

P
(ii) dil. KMnO4 (excess), 273 K

26. In the reaction given below, the total number of atoms having sp2 hybridization in the major product P is
______. [JEE (Adv)-2021 (Paper-1)]
1. O3 (excess)
then Zn/H2O
P
2. NH2OH
(excess)
27. The number of -CH2- (methylene) groups in the product formed from the following reaction sequence
is ________. [JEE (Adv)-2022 (Paper-2)]

  

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