CPP - HYDROCARBON - SHEET – 5

t  BuOK
CH3  
1. F Product. Choose the major products.

CH3
(a) is an endocyclic saytzeff product

CH2
(b) is an exocyclic saytzeff product

CH3
(c) is an endocyclic Hoffmann product

CH2
(d) is an exocyclic Hoffmann product

Passage # 1
An alkane (A) molecular formula C6H14 reacts with chlorine in the presence of ultra violet light to
yield three isomeric monochloro derivatives (B) , (C) and (D) . Of these only (C) and (D)
undergo dehydrohalogenation with sodium ethoxide in ethanol to produce an alkene . Moreover
(C) and (D) yields the same alkene (E) (C6H12) . Hydrogenation of (E) produces (A) . Treating (E)
with HCl produces a compound (F) that is an isomer of (B) , (C) and (D) . Treating (F) with Zn
and acetic acid gives a compound (G) , which is isomeric with (A). Propose structures for (A) to
(G) .
2. The structure of A is
CH3

(A) CH 3 –CH 2 –CH 2 –CH 2 –CH 2 –CH 3 (B) CH3–CH–CH2–CH2–CH3

CH3
CH3–C–CH2–CH3 CH3 CH3

(C)
CH3 (D) CH3–CH–CH–CH3

3. The structure of G is
CH3 CH3 CH3

(A) CH3–CH2–CH–CH2–CH3 (B) CH3–CH––CH–CH3

CH3

CH3 CH3–C–CH2 –CH3

(C) CH3–CH–CH2–CH2–CH3 (D) CH3

4. The compound (F) on treatment with alcoholic KOH, the major product obtained is
(A) 1-hexene (B) 2,3-dimethyl-2-butene
(C) 2,3-dimethyl-1-butene (D) 3-hexene
5. Which of the following reactions is expected to give a fairly good yield of (CH 3 )3 C  CH  CH 2 ?

CH3 OH CH3 Br

H3C C CH - CH3 H3C C CH - CH3

(A) (B)
CH3 H2SO4 CH3 Zn, acetone
 

CH3
H3C CH2CH3 CH3 Br
CH3N
H3C C CH - CH3
(C) (D)
CH3 C CH - CH3
CH3 Me3CO
CH3 OH,  

Br Br
6. CH - CH 
Zn, dust


Br Br

Br H Br Br
(A) C=C (B) C=C
H Br H H
Br
(C) H  C  C  H (D) CH3 - CH
Br

CH2 
7. 
H ,H 2 O


Major product is :
OH
(A) (B) (C) (D)
OH OH OH

8. CH2 
Br2
CH3 OH
 A 
KCN
B :

CH2 - Br CH2 - Br
(A) B is (B) B is
CN OCH3

CH2 - Br CH2 - C N
(C) A is (D) B is
OCH3 OCH3

9. In the following reaction A is.

CH3

Ph Br

alc KOH


Ph Br

CH3
Major product , major product is :
 Ph CH2 Ph CH2

(A) (B)
Ph CH2 H2C Ph
Ph CH3

(C) (D) None of these

H3C Ph

Passage - 1
E1 reaction is first order reaction with respect to the substrate. Product formation takes place via
formation of carbocation as reactive intermediate. The rate of E1 reaction depends on both the
ease with which the leaving group leaves and stability of the carbocation that is formed. Product
formation mostly takes place by Saytzeff rule.

10. Which one of the following is most reactive towards E1 reactions?

Br I
(a) C6H5CHCH3 (b) C6H5CHCH3
Cl F
(c) C6H5CHCH3 (d) C6H5CHCH3

11. Which one of the following will be most reactive towards E1 reaction?
Br Br
(a) CCH2CH3 (b) C6H5CHCH3

Br Br
(c) CH2=CHCHCH3 (d) CH2=CHCCH3
CH3
CH3
HCBr NH2–
12. 
(A) . The compound (A) will be
BrCH
CH3
(a) cis alkene. (b) trans alkene.
(b) may be cis or trans alkene. (d) alkyne

13. How many alkenes are formed by E1-eliminting e.g. HCl from
3-chloro-3, 5-dimethyl-4-ethylheptane in methanol. (excluding stereoisomers)

14. How many alkenes are formed by E2 – eliminating of 2-Bromo-2, 3, dimethyl hexane using strong
base.

15. Ease of -dehydrobromination among these substrate under the treatment of strong base will be
in order
CH3

Br Br Br

(I) (II) (III)

 Br
16.

alc.
KOH
 major products

CH3

17. CH3 

alc. KOH

(A)

Br

Br

18. Ph CH CH2 

x mol
NaNH
 Ph— C  CNa  x is
2

Br

19. Order of reactivity of the following isomeric hexachlorocyclohexanes for -dehydrohalogenation as

treatment using strong base is
Cl Cl Cl
Cl Cl Cl Cl Cl Cl

Cl Cl Cl Cl Cl Cl
Cl Cl Cl
(I) (II) (III)

Cl
H3C H
20.

alc KOH


D D

H
21.
H 
alc
KOH
 Pr oduct

Br

CH3
CH

KOD excess
D2O
 Pr oduct
F
22.
CH3
O CH
NR3
 ANSWER SHEET - 5
1. D
2. C
3. B
4. B
5. D
6. C
7. B
8. C, D
9. B
10. B
11. A
12. D
13. 3
14. 2
15. II  III  I
16. Trans Butene
17. CH3

CH3
18. 3
19. I  III  II
20. H3C H

21.

22. CD CH CH3

C
O CD CH2