HALOGEN DERIVATIVES Page # 47

Exercise - III (Only one option is correct)

Br
Br
1. CH3 — CH2 — CH2 — C — CH3 |
5. —C — CH2 — CH3
CH3 |
CH2 — CH2 — CH3
Identify all possible product obtained by E2 Total number of products obtained when this
reaction ? substrate is subjected to E2 reaction will be
(including streoisomer)
(A) CH3 — CH2 — CH2 — C = CH2 (A) 3 (B) 4
(C) 5 (D) 6
CH 3

CH 3 Br
(B) CH3 — CH2 –CH = C
6.
CH3

(C) both (A) and (B)

The major products obtained when this
(D) none of these
substrate is subjected to E2 reaction will be

+
H Br2
2. (A) (B)
major
CCl4 (A) (B)
OH

Product (B) is (C) both (A) and (B) (D) none of these
(A) meso (B) Racemic
(C) Diastreomer
(D) optically active single products CH3
Br
7. CH3
Br
Zn
3. + ZnBr2
Br The major products obtained when this
This reaction is a case of substrate to E2 reaction under the treatment
(A) -elimination (B) -elimination of potassium tert-butoxide will be
(C) -elimination (D) none of these
CH2

4. Most reactive towards acid-catalyzed (A)

hydrolysis is CH3
OEt
(A) (B) OEt
OEt CH3

(B)
(C) EtOEt (D) EtOH
CH3

(C) both in equal proportions

(D) none of these

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 Page # 48 ALKYL HALIDE

(A) Rate = k[RX] (B) Rate = k [RX]2

(C) Rate = k[RX][base]
CH 3 CH3
(D)Rate = k[base]
8. I II
12. Which alkyl bromide will yield only one alkene
Br
Br upon E2 elimination ?
CH3
CH3
(A) (B) Br
III Br

Br Br
Ease of -dehydrobromination among these
substrates under the treatment of strong base (C) (D)
will be in the order as Br
(A) i > ii > iii (B) iii > ii > i
(C) ii > i > iii (D) ii > iii > i
13. Which alkylbromide will yield-3-methyl-1-
hexene as the major product upon treatment
9. Which of following cannot undergo an E2 with potassium t-butoxide in t-butyl alcohol
reaction ? (solvent) ?
Br
H3C CH2Br H3C Br
(A) (B)
CH3
Br
(A) (B)

(C) (D)
Br
Br
CH2Br
CH3 14. In order to accomplish the following conversion,
what reagent and conditions would be required
(C)
?

(A) A (B) B ?
(C) C
(D) None (all can undergo an E2 reaction)

Cl

10. Major product of the reaction is (A) Cold sodium hydroxide

(B) Hot conc. sodium hydroxide
Br
(C) Potassium t-butoxide and heat
alc. KOH
CH3 — C — CH2 — CH3 (D) Hot water

(A) Butene-1 (B) Trans-2-butene 15. Cl Cl Cl

(C) cis-2-butene (D) Butyne-1
I II III
11. Which of the following expressions is the which is most easily dehydrohalogenated ?
experimentally observed rate law for an E2 (A) I (B) II
reaction of alkyl halide ? (C) III (D) All with same ease

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 HALOGEN DERIVATIVES Page # 49

CH3OH CH 3
+
16. CH3O — CH = CH2 H product formed
20.
is
(A) Acetal (B) Hemiacetal Br
(C) Alcohol (D) aldehyde CH3

CH3 The major product obtained when this

substrate is subjected to E2 reaction will be
17. CH3 CH2

Cl (A) (B)

Total number of SN 1 products of given

compound are
CH3 CH3
(A) 3 (B) 4 (C) both (A) and (B) (D) none of these
(C) 5 (D) 6
21. Which of the following isomeric
hexchlorocyclohexanes is least reactive in ()-
Br
dehydrochlorination of treatment with strong
18. CH3 — CH2 — CH2 — C — CH2 — CH3 base
Cl
CH3
Cl Cl
Total number of SN1 + E1 products obtained
will be - (A)
(A) 5 (B) 6 Cl Cl
(C) 7 (D) 8
Cl
Cl

CH3 Cl Cl
+
19. CH3 — C — CH2 — CH3 H (B)

CH3 OH Cl Cl

Cl
Cl

(A) Cl Cl

OH (C)

Cl Cl

+ OH + Cl
H (B) H (C)

Stability of product (A), (B), (C) is :

(A) C > B > A (B) A > B > C
(C) B > C > A (D) C > A > B

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 Page # 50 ALKYL HALIDE
(D) all three are equally reactive

22. If the following E2 reaction proceeds through

H3C H
an anti-periplaner transition state, what
products are expected ? (A)
CH 3
H CH3

H3C H
Cl
(A) Only 3-methylcyclohexene (B)
(B) Only 1-methylcyclohexene
(C) The major product is 3-methylcyclohexene H3C H
and the minor product is 1-methyl cyclohexene
(C) both (A) & (B) (D) none of these
(D) The major products is 1-methylcyclohexene
and the minor product is 3-methyl cyclohexene
alc. KOH X
26. CH3 — CH2 — CH — CH3
Major
23. The nitrogen atom in each of the following
Br
tertiary amines may be removed as trimethyl
amine by repeated Hofmann eliminations EtONa
Y
(exhaustive methylation followed by heating ; CH3 — CH2 — CH — CH3 Major
with AgOH).
NMe3
Which of the amines requires the greater +
number of Hofmann sequences to accomplish Product (X) and (Y) respectively is
this ? (A) 1-butene, trans-2-butene
CH3 (B) 1-butene, cis-2-butene
N
(C) cis-2-butene, 1-butene
(A) (B) (D) trans-2-butene, 1-butene
N
27. Predict the major product of the following
N(CH3)2 CH3 reaction :
N
H2SO4
(C) (D) CH3CH2CHCH2OH
| heat
CH3

24. Correct order of yield of Hofmann alkene in CH 3

|
following reaction will be (A) CH 3CH 2C = CH 2
CH 3CH 2CHCH 3 X may be F, Cl Br or l (B) CH3CH = C(CH3)2
|
X (C) CH3CH = CHCH2CH3
(D) (CH3)2CHCH = CH2
(A) F > Cl > Br > l (B) l > Br > Cl > F
(C) Cl > F > Br > l (D) l > Br > F > Cl

Br CH 3
H3C H
28.
25. ? major
—Br2 Br
H CH3 CH3
Br
products is :
The major product obtained when this
substrate is subjected to E1 reaction will be

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 HALOGEN DERIVATIVES Page # 51

CH 3 CH3
(A) (B)

CH2 CH3

CH3

(C) (D) none of these

CH3

conc. H2SO4
29. major product
OH
having H
(A) 12  H (B) 8  H
(C) 4  H (D) 11  H

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