Chapter 21

Hydrocarbons
1. Answer (B)
2. Answer (D)
Br

CH2—CH2 —CH2 —CH3

NH2
CH3—CH2—C C—H CH3—CH2—CC CH 3—CH2—CC—CH2—CH2—CH2—CH3
3-octyne
3. Answer (C)

COOH COOH
HNO3/H2SO4

HO HO
NO2

OCH3 HNO3/H2SO4 OCH3

H3C H3C NO2

O O NO2

C HNO3/H2SO4
C
O O

4. Answer (B)

H (sp) H
C=C=C
H H
(sp2) (sp2)
(Allene)

5. Answer (A)
Ozonolysis produces CH3CHO and CH3–CH(CHO)2.
6. Answer (B)
As branching increases boiling point decreases, so order of boiling point is III > II > I.
7. Answer (B)
It is a case of Birch reduction. Alkynes on reaction with alkali metal in liq. NH3 gives trans-alkene. But terminal
alkynes do not get reduced.

NaNH 2
Na
liq. NH3

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8. Answer (B, D)

X H3C CH3
H3C CH3
X C
C
H H H HY
Y

When X = H & Y = C2H5

H3C CH3
H C
2
C C2H5
H 1 H

2, 2- dimethyl butane
When X = CH3 and Y = CH3

H3C CH3
C2
4CH3
C CH3
H 3 H 1

2, 2-dimethyl butane
9. Answer (D)

CH3
CH2 1 equiv. HBr
H2C H
+
H3C 

 Br
–
Br

(Major)

10. Answer (B, C, D)

Br

+
NaOEt

–
AlCl3 + 1, 2 H +
Shift
Cl

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+
H +

BF3 1, 2 H– +
+
O–H Shift
H

11. Answer (B, D)

HC
3
H CH3 CH3
(i) C=C (ii) C=C
H CH 3
H Cis H
Trans
Br2
Br2 /CHCl3

CH3 CH3
CH CH
3 3
H Br Br H
H Br Br H +
+ Br H H Br
H Br Br H
CH3 CH3
CH CH
3 3
O P
Meso (M and N) Pair of enantiomers

Cis anti Racemic

M and N are meso (identical)
O and P are pair of enantiomers
(B) Bromination proceeds through anti addition.
(D) (M and O) and (N and P) are two pairs of diastereomer.
12. Answer (B, D)
Br
EtO
(A) (Anti Aromatic)
H
Me
(i) Alc. KOH
(B) Br Br (ii) NaNH2 Me — C º CH
Red hot Fe tube, 873 K

Cl
Cl Cl
UV
(C) + 3Cl2
500 K Cl Cl

H Cl

(D) MeO
+ MeOH

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13. Answer (B, C)

Me
(A) Zn
CH3—CH == CH2
Br Br

NaOH–CaO
(B) COOH 

(C) Zn
Cl +
H

(D) 2 COONa + 2H2O

Electrolysis
+ 2CO2 + H2 + 2NaOH
14. Answer (B, C)

X Pd-C/Quinoline/H2

*
R

(P)
(ii) KMnO4/H2SO4/

*COOH
COOH
COOH
(Q)
15. Answer (D)
16. Answer (B)
Solution of Q. Nos. 15 and 16

O (i) NaBH4 OH
H3C 2+ + H3C H3C
Hg /H3O (ii) dil H
+

H3C C – C C–H H3C C – C H3C C – C – H

H3C H3C CH3 H3C CH3

H3C H H3C H 
–H
   H
C – C – CH3 H3C C – C
H3C CH3 H3C CH3

(i) O3
H3C CH3 CH3
(ii) Zn–H2O
C C 2 C O
H3C CH3 CH3

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17. Answer (A)

NaNH2 – + CH3 CH2 I

H C Na C
+ – (1 eq) + –
HO Na O Na O
CH3 I

CH3
H2
CH3 O
O Lindlar's
H H catalyst

18. Answer (C)

1. NaNH2 (2 eq ) O
2. OH
Br
H +
3. H3O (mild)
4. H2, Pd/C
5. CrO3

19. Answer (C)

OH

Pd-BaSO4 i. B2H6
C8H6
H2 ii. H2O 2, NaOH, H2O

20. Answer (D)

H2O
C8H6
HgSO4
H2SO4
i. Et MgBr, H2O
+
ii. H , Heat

21. Answer (A)

H – C H(CH3)2 HC – CH3
CH 3

H – C H2Ph CH2 – Ph
Benzyl radical

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H – CH = CH2  CH = CH2

H – C  CH  C  CH
Order of stability of free radical
Q>P>R>S

1
Stability of free radical  Bond energy

 Order of bond energy :

S>R>P>Q
22. Answer (D)
(1) Cl2  2Cl (Initiation step) H = 58 kcal/mol
(2) CH4 + Cl  CH3 + HCl 
CH  Propagation step
(3) 3 + Cl2  CH3Cl + Cl 
Step (1)  Endothermic (bond breaking)
Step (2)  H = 105 – 103
= 2 kcal/mol (Endothermic)
Step (3)  H = 58 – 85
= –27 kcal/mol (Exothermic)
For complete reaction

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

H = 58 + 105 – 85 – 103
= –25 kcal/mol
23. Answer (A)

NaOEt
(P) Cl

(Q) ONa + Et-Br OEt

(1) Hg(OAc)2 OH
(R)
(2) NaBH4

(1) BH3
(S) (2) H2O2/NaOH
OH

24. Answer (4)

Aqueous dilute
OH
+
H H KMnO4 (excess)
Heat

HO OH
HO
(P) OH

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25. Answer (6)

(i) H2, Pd-BaSO4, quinoline

HO
(ii) dil. KMnO4 (excess)
OH
273 K
HO OH

OH

OH

26. Answer (8) or (12)

O O

O O

+ +
OH OH OH OH

N N N N

2. NH 2OH (–) (–)

(–) (–)
(excess)

N N N N
+ +
OH OH OH OH
(P)

The total number of atoms having sp2 hybridisation in the major product (P) = 12
This includes 4 C-atoms, 4 N-atoms and 4 O-atoms.
If only 4 C-atoms and 4 N-atoms are considered, then only 8 sp2 -hybridised atoms will be present in the
final product. Officially JEE gave 8 and 12 as the correct answer.

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27. Answer (0)



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