Halogen Compounds CHEMISTRY

EXERCISE-II [Previous Exam Questions]

1. An organic compound A(C4H9Cl) on 6. Among the following, the one which
reaction with Na/diethyl ether gives a reacts most readily with ethanol is
hydrocarbon which on monochlorination [AIIMS-2004]
gives only one chloro derivative than, A (1) p-nitro benzyl bromide
is [AIPMT-2001] (2) p-chloro benzyl bromide
(1) t-butyl choride (3) p-methoxy benzyl bromide
(2) Sec. butyl chloride (4) p-methyl benzyl bromide
(3) Iso butyl chloride 7. The major product obtained on treatment
(4) n-butyl chloride of CH3CH2CH(F)CH3 with CH3O–/CH3OH

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is – [AIIMS-2005]
2. Reactivity order of halides for dehydro- (1) CH3CH2CH(OCH3)CH3
halogenation is - [AIPMT-2002] (2) CH3CH=CHCH3
(1) R–F > R–Cl > R–Br > R–I (3) CH3CH2CH=CH2

TO
(2) R–I > R–Br > R–Cl > R–F (4) CH3CH2CH2CH2OCH3
(3) R–I > R–Cl > R–Br > R–F 8. Which of the following undergoes
(4) R–F > R–I > R–Br > R–Cl nucleophilic substitution exclusively by
SN1 mechanism? [AIPMT-2005]

3.
MgBr
(i)CO

2
P, In the above reaction
IT (1) Ethyl choride
(2) Isopropyl chloride
CH

(ii)H3O (3) Benzyl chloride
product 'P' is [AIPMT-2002] (4) Chloro benzene
CHO COOH
9. Which of the following is least reactive
(1) (2)
in a nucleophilic substitution reaction?
P

OH O [AIPMT-2007]
EE

(1) CH2=CHCl (2) CH3CH2Cl

(3) (4) C6H5–C–C6H5 (3) CH2=CHCH2Cl (4) (CH3)3C–Cl

10. In a SN2 substitution reaction of the type

4. When CH3CH2CHCl2 is treated with
D

R–Br + Cl DMF 

 R–Cl + Br , which
NaNH2, the product formed is :
one of the following has the highest
[AIPMT-2002]
A

relative rate? [AIPMT-2008]

(1) CH3–CH=CH2
CH3 CH3
(2) CH3–CCH
PR

NH2 (1) CH3–CH–CH2Br (2) CH3–C–CH2Br

(3) CH3CH2CH
NH2 CH3
Cl (3) CH3–CH2Br (4) CH3-CH2-CH2Br
(4) CH3CH2CH
NH2
11. Which one of the following is most
reactive towards electrophilic attack ?
5. Among the following the most reactive
[AIPMT-2008]
towards alcoholic KOH is [AIIMS-2004]
(1) CH2=CHBr NO2 OH
(1) (2)
(2) CH3COCH2CH2Br
Cl CH2OH
(3) CH3CH2Br (3) (4)
(4) CH3CH2CH2Br
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CHEMISTRY Halogen Compounds

12. Which of the following reactions is an 16. Which of the following compounds
example of nucleophilic substitution undergoes nucleophilic substitution
reaction? [AIPMT-2009] reaction most easily?
(1) RX + Mg  RMgX [AIPMT MAINS-2011]
(2) RX + KOH  ROH + KX Cl
Cl
(3) 2RX + 2Na  R – R + 2NaX (1) (2) NO 2
(4) RX + H2  RH + HX
Cl Cl
13. Trichloroacetaldehyde, CCl3CHO reacts
with chlorobenzene in presence of sulphuric (3) (4)
acid and produces - [AIPMT-2009]

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(1) Cl CH Cl CH3 OCH3
CCl3
Cl 17. Consider the reactions :

TO
(2) Cl C Cl [AIPMT MAINS-2011]
C2 H5OH
CH2Cl (i) (CH3)2CH–CH2Br  
Cl (CH3)2CH–CH2OC2H5 + HBr

IT

C 2 H 5O
(ii) (CH3)2CH–CH2Br  
(3) Cl C Cl (CH3)2CH–CH2OC2H5 + Br–
CH
H The mechanisms of reactions (i) and (ii)
OH
are respectively :
(4) Cl C Cl
(1) SN2 and SN1 (2) SN1 and SN2
Cl
14. In the following reaction (3) SN1 and SN1 (4) SN2 and SN2
P

1.Mg,Ether
C6H5CH2Br  X,
2.H O
EE

3
18. Which of the following compounds will
Product 'X' is – [AIPMT Mains-2010]
(1) C6H5CH2OH give a yellow precipitate with iodine and
(2) C6H5CH3 alkali? [AIPMT Mains 2012]
D

(3) C6H5CH2CH2CH2C6H5 (1) Acetamide

(4) C6H5CH2OCH2C6H5 (2) 2-Hydroxypropane
A

15. Which one is a nucleophilic substitution (3) Acetophenone

(4) Methyl acetate
PR

reaction among the following?

[AIPMT-2011]
(1) CH3CHO + HCN  CH3CH(OH)CN 19. Arrange the following compounds in order
H2 O
(2) CH3–CH=CH2   CH3–CH–CH3 of their boiling point. [AIIMS-2016]
H
CH3
OH
(I) CH3–C–Br
(3) RCHO + RMgX  R–CH–R
CH3
OH (II) H3C–CH–CH 2–CH3
CH3 Br
NH3
(4) CH3–CH2–CH–CH 2Br  (III) CH3–CH2–CH2–CH2–Br
CH3 (1) I > II > III (2) III > II > I
CH3–CH2–CH–CH 2NH2 (3) II > I > III (4) III > I > II

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 Halogen Compounds CHEMISTRY

CH3 Cl CH3ONa 23. Cl2 / h

 Product of reaction is
20. C   Product (Major)?
H C6 H 5
[AIIMS-2017]
[AIIMS-2017]
CH3 OCH3 C6H5 OCH3 Cl
CH2–CH3
(1) C (2) C (1) (2)
H C6 H 5 H CH3 Cl
CH3 C6H5
(3) C (4) C6H5–CH=CH2 (3) CH2–Cl
(4)

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H OCH3
Cl
21. Correct order of reactivity towards
24. Product of following reaction is :
nucleophilic-substitution reaction of

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Br
following is : [AIIMS-2017] Zn dust
Br  
[AIIMS-2017]
CH2–CH2–Cl CH2–Cl
(I) (II) (1) (2)

IT
Cl Cl (3) (4)
(III) (IV)
CH
25. Compound A, C8H10O, is found to react
OCH3 NO2 with NaOI (produced by reacting Y with
(1) II > I > IV > III (2) III > IV > I > II NaOH) and yields a yellow precipitate
(3) II > IV > I > II (4) IV > II > III > I with characteristic smell. A and Y are
P

respectively : [NEET-2018]
22. Which of the following react fastest with CH3
EE

(1) CH3 OH and I2

aqueous acetone? [AIIMS-2017]
(2) CH–CH3 and I2
(1) (2) OH
D

Br Br (3) CH2–CH3–OH and I2

Br (4) H3C CH2–OH and I2
A

(3) (4)
PR

Br

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PR
A
D
EE
P
CH
IT
TO
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