HALOGEN DERIVATIVES Page # 63

Answers
Exercise-I

1 B 2 B 3 B 4 C 5 C 6 A 7 A 8 A 9 B
10 C 11 C 12 C 13 B 14 C 15 C 16 C 17 A 18 D
19 A 20 A 21 C 22 C 23 B 24 A 25 A 26 A 27 C
28 B 29 B 30 B 31 A 32 C 33 A 34 C 35 A 36 A
37 C 38 D 39 B 40 B 41 B 42 A 43 C 44 C 45 C
46 A 47 A 48 B 49 D 50 B

Exercise-II

1 B 2 B 3 C 4 A 5 C 6 A 7 A 8 D 9 C
10 A 11 C 12 D 13 B 14 A 15 B 16 B 17 A 18 D
19 A 20 D 21 A 22 A

Exercise-III

1 C 2 A 3 B 4 A 5 C 6 B 7 A 8 D 9 A
10 B 11 C 12 B 13 D 14 C 15 A 16 A 17 B 18 C
19 D 20 D 21 B 22 A 23 A 24 A 25 A 26 D 27 B
28 B 29 B

Exercise-IV

1 ABD 2 BD 3 ABC 4 AB 5 BC 6 B 7 AB 8 A 9 A
10 B 11 D 12 D 13 A

Exercise-V
1 A S ; B R ; C Q ; D P 2 A T ; B S ; C R ; D Q; E P
3 A P, Y ; B Q, X ; C R, W 4 A S ; B R ; C Q ; D P

5 A R ; B Q ; C P ; 6 A P ; B Q ; C R ; D S; E T

7 A S ; B Q ; C R ; D P 8 A 2 ; B 1 ; C 4 ; D 3

9 A S ; B R ; C Q ; D P 10 A S ; B Q ; C P ; D R

11 B 12 A W ; B XY ; C WY ; D Z

13 A P ; B Q, S ; C Q, R ; D R, S 14 A P ; B R ; C Q ; D T

15 A S ; B R ; C P ; D S

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 Page # 64 ALKYL HALIDE

S.NO. SN1 SN2 BOTH

1 
2 
3 
4 
16. 5 
6 
7 
8 

Exercise-VI(A)
1 C 2 A 3 A 4 C 5 A 6 B 7 D 8 A 9 D

10 D 11 A 12 A 13 C 14 D 15 B 16 B 17 AD

18 A Q ; B Q ; C R, S ; D P, S 19 0005 20 A 21 C 22 AD 23 C

24 B 25 A 26 D 27 A 28 C 29 B 30 B 31 B 32 D
33 A 34 A 35 D 36 D 37 C 38 B

Exercise-VI(B)

1. Butaol has capacity for inter molecular hydrogen bonding.

Boil OH
2. CH3CH2 CHCl2 CH3— CH2—CH CH3 – CH2 – CHO
alkali –H2O
–2NaCl OH propanal
(unstable)

3. (a) propyl chloride, (b) ortho

4. CH3 – C = CH – CH3

CH3
5. Due to the presence of resonance in alkyl halide carbon halogen bond acquires the character of partial
double bond and halogen is directly attached to SP2 hybridised carbon so the halogen is not capable to leave
as an leaving group.

6. This product after the reaction contain equal amount of both d and l-isomers of 2-iodobutane and this
racemic mixture does not show optical activity due to external compensation.
CH3 CH3 CH3 CH3

7. (X) : CH 3 – C – CH – CH 3 ; (Y) : CH2 = C – CH – CH3 ; (Z) : CH3 – C – CH – CH3

Cl CH3 CH3

CH3 CH3 CH3

Conc. H4SO4
CH3 – C – CH – CH3 CH 3 – C = C – CH 3 – H2O
8.
(major product)
CH 3 OH
Mechanism of above reaction is represented as follows :

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 HALOGEN DERIVATIVES Page # 65

CH3 CH3
+
H
CH3 – C — CH – CH3 CH3 – C — CH – CH3
+
CH3 :..
OH CH3 OH2

CH3 H CH3
+ +
CH3 – C — CH – CH3 CH3 – C — CH – CH3
–H2O
CH3 CH3
(more stable) (less stable)
+
–H
CH3 CH3

CH3 – C = C – CH3 (major product)

CH3 CH3 CH 3 CH3 CH3 CH3

9. CH3 – C — CH – CH3 ; (Y) CH2 = C — C – CH 3 ; (Z) CH3 – C = C – CH3

Cl
10. The oxirane ring is cleaved by the following mechanism.

H3C H3C OH
+ +
H H2O H3C – C — CH2 + H
H3C .. H3C +
O
.. O CH3 OH

H
11. In these two methods, method (ii) is the correct method for the formation of ether because in method
(i), alkene is formed in place of ether.
(i) (CH3)3C – Br + Na – O – Me CH3 – C = CH2 + NaBr + CH3OH

CH3
iso-butene
CH3
+ –
(ii) CH3Br + NaO – C(CH3)3 H 3C – C – O – CH3 + NaBr

CH 3
This reaction is called as Williamson's synthesis and it is based upon SN 2-reaction mechanism.

12. Due to formation of more stable 3º-carbonium ion with t-butanol that 1ºcarbonium ion in n-butanol.

+
H
CH3 – CH 2 – CH 2 – CH2OH
–H2O
n-butanol
+
CH 3 – CH 2 – CH 2 – CH 2

1º-carboction
although it is changed
+ in 2º-carbocation
CH 3 – CH 2 – CH – CH3

CH 3 CH 3
+
H +
CH3 – C – OH CH 3 – C (3º-carbocation)

CH3 CH3

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CH 3
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CHI + CH3I
13. (a) Cis and trans forms of stibene C6H5CH = CHC6H5 (b)
CH 3
 Page # 66 ALKYL HALIDE

CH3
14. (i) CH3 – C = CH – CH3

15. Ethyne

16. (i) Methane does not react with chlorine in the dark because chlorine atoms are required for this
reaction and chlorine atoms are obtained only in the presence of light.
(ii) It is accordance with Markownikoff's rule which predicts the stability of secondary carbonium ion
over primary carbonium ion.

17. sp 3
18. CH2 KMnO4 CH2OH
+ [H2O + O]
CH2 CH2OH
CH2 CH 2OH
2KMnO4 + 3 + 4H2O  3 + MnO2 + 2KOH
CH2 CH 2OH

Me Me
H Br Br H
19. +
Br H H Br

Me Me
H2
20. (C5H8) C5H 12
(hydrogenation)
CompoundE CompoundF

Ozonolysis
HCHO + H 3C – C – CHO
formaldehyde
O
2-ketopropanal
Hence, compound E must be diene.
CH2 = C – CH = CH2

CH3
Compound F = CH3 – CH – CH2 – CH3

CH3

21. (A) (B)

25. (A) CH3 – CH2 – CH = CH – CH2 – CH3 (B) CH3CH2COOK

22. Resonance is present in 1, 3-butadiene that's why every bond acquire the character of partial double
bond.

23. Higher electronegativity of sp carbon

O
24. , (Y) CH 3 – C – (CH2) 4 – CH = O
CH3

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