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Manzil JEE (2024)

Haloalkanes and Haloarenes JEE
Practice Sheet

Single Correct Type Questions (1-15) 4. Chloroform on reaction with acetone gives:-
1. Which of the following can not give SN1 reaction (1) Acetylene (2) Chloretone
easily? (3) Nitrochloroform (4) Chloroacetone

5. Which reaction gives elimination as a major product

(1) (2)

(1)
DMSO
(2) CH3 – CH2 – Br + NaCN  
Dryacetone
(3) (4) (3) CH3 – CH2 – Br + Nal  

2. Which one of the following compounds will be most

reactive for SN1 reactions? (4)

6. Which will give yellow ppt. with iodine and alkali

(1) Propan–2–ol (2) Benzophenone
(1) (2) (3) Methyl acetate (4) Acetamide

7. Which of the following undergoes hydrolysis most

easily. Then,

(3) (4) (1)

(2)
NaOH
3. 
 &pressure

(3)
Rate of reaction is maximum if G is :-
(1) –OCH3
(2) –CH3
(3) –NO3 (4)
(4) –H
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8. In which of the following replacement of Cl– is most

difficult? SOCl2
13.   (A). The product A will be
Pyridine

(1)

(2)
(3) (1) (2)

(3) H2C = CH2 (4)

(4)

14. What will be the major product, when 2-methyl

butane undergoes bromination in presence of light?
9. Which reaction proceeds faster with Nal in DMSO?
(1) 1-Bromo-2-methyl butane
(2) 2-Bromo-2-methyl butane
(1) (2) (3) 2-Bromo-3-methyl butane
(4) 1-Bromo-3-methyl butane

(3) (4) 15. HOH

 Products. (If 96% racemization

takes place)
10. The given compound CH3–O–CH2–Br gives which Find out the correct statement about the reaction.
one of the following reactions: (1) Among the products 48%S and 48%R
(1) Only SN1 configuration containing molecules are present
(2) Only SN2 (2) Among the products 50%S and 50%R
(3) SN1 as well as SN2 configuration containing molecules are present
(4) E1 only (3) Among the products 48%S and 52%R
configuration containing molecules are present
11. When ethyl bromide is treated with moist Ag2O, the (4) Among the products 52%S and 48% R
main product is: configuration containing molecules are present
(1) Ethyl ether More Than Type Questions: (16 to 17)
(2) Ethanol 16. Rate of SN2 depends on
(3) Ethoxy ethane (1) Conc of Nucleophile
(4) All of these (2) Conc of substrate
(3) Nature of leaving group
12. When ethyl bromide is treated with dry Ag2O, the (4) Nature of solvent
main product is:
(1) Ethyl ether 17. SN1 and SN2 is not favourable in
(2) Ethanol (1) H2C = CH–Cl (2) Ph–CH2–Cl
(3) Ethoxy ethane (3) Ph–Cl (4) H2C = CH–CH2–Cl
(4) All of these
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Passage Type Questions: (18 to 20) 20. What would be the product of the given reaction?
Because of the resonance stabilization of Arylhalides they
are unreactive towards normal nucleophilic substitution
reactions. However arylhalides having strong electron
withdrawing groups at ortho and para positions give
aromatic nucleophilic substitution reactions (SNAr
mechanism), which involves a resonance stabilized
(1)
carbanion called Meisenheimer complex.

(2)

(3)

(4)

18. Which arylhalide is most reactive towards S NAr Match the Column Type Questions: (21 to 22)
mechanism? 21. Match List-I with List-II.
List I
alc.KOH
(1) (A) CF3  CHCl2  CF2  CCl2
CH 3
| CH3  C  CH 2
H
(2) (B) CH3  C  OH   |
| CH 3
CH 3
(3) alc.KOH
(C) CH3  CH2  Br 

 CH2  CH2
Br
| CH3  C  CH 2
(4) EtOH
(D) CH3  C  CH3 
 |
| CH 3
19. Which of the following statement is/are true? CH 3
(1) SNAr proceeds through elimination / addition List-II
mechanism (P) Elimination Reaction
(2) Formation of elimination product is the rate (Q) Carbocation
determining step (R) Carbanion
(3) Formation of Meisenheimer complex is the rate (S) Free radical
determining step (1) A  P, R; B  P, Q; C  P; D  P, Q
(4) SNAr mechanism involves inversion of (2) A  Q, R; B  P, Q; C  P; D  P, Q
configuration (3) A  P, R; B  P, Q; C  P; D  R, Q
(4) A  P, R; B  R, Q; C  P; D  P, Q
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22. Match List-I with List-II. 24. How many of the given reagents can be used to
List I (Reactions) convert alcohol into alkyl halide?

(A) CH3  O  SO2CH3  C2 H5 O I. NaBr II. NaCl
III. HBr IV. PCl3
(B) CH3–CH2–I + PH3
 V. SOCl2 VI. HCl (conc.)/ZnCl2 (anhyd.)
(C) HC  C Na  CH3  CH2  Br VII. NaI VIII. HI IX. PCl5

(D) CH3  Cl  CH3  O
25. Total number of monochloroderivatives (including
List-II (Products)
stereoisomers) possible for the given compound
(P) CH3–CH2– PH2
(Q) CH3–O–C2H5 would be
(R) CH3–O–CH3
(S) CH  C–CH2–CH3
(1) A  Q; B  P; C  S; D  R
(2) A  P; B  S; C  R; D  Q
(3) A  P; B  Q; C  R; D  S
(4) A  Q; B  S; C  P; D  R

Integer Type Questions: (23 to 25)

23. Total type of reactions of an alkyl halide can give
out of the given reaction type
I. SN1 II. SN2
III. E1 IV. E2
V. EICB VI. SNi
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Answer Key
1. (3) 13. (2)
2. (1) 14. (2)
3. (3) 15. (3)
4. (2) 16. (1, 2, 3, 4)
5. (4) 17. (1, 3)
6. (1) 18. (1)
7. (4) 19. (3)
20. (2)
8. (4)
21. (1)
9. (2)
22. (1)
10. (3)
23. (5)
11. (2)
24. (6)
12. (3)
25. (6)
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Hints & Solutions

1. (3) 5. (4)
(1)
CH3 CH3
H3C – C – O H3C – Br H3C – C – O – CH3
Cl CH3
(+R) (7  H) (Anti-Aromatic) +R (2)
Rate of SN1  stability of C H3C  CH2  Br  NaCN  H3C  CH2  CN
(3)
III  Anti-Aromatic ,  unstable C
Dry
 SN 1 is unfavourable CH3  CH2  Br  NaI 
 H3C  CH2  I
acltone
CH3 CH3
2. (1)
| |
Rate of SN1  stability of C 
(4) H3C  C  Br  CH3O Na  H3C  C
| ||
O O O CH3 CH 2
(Tert-alkyl  prefers elimination sterically
O halide hindered
But, L.G. (I  Br   Cl ) & (R) (4  H)
6. (1)
3. (3) 
Cl The reagent I 2 |O H and yellow ppt. indicates
iodoform reaction.
OH O
| ||
I2 I
G 1. H3C  C  CH3  CH3  C  HI 
2

(Nucleophilic substitution reaction is very difficult | |

on haloarene). H CH3
 High T, high P (Becomes favorable)
 G = E W G (  reactivity of haloarene)
 (NO2 is E WG)

4. (2)

Cl O Cl OH
| || | | 2.
Cl  C  H  H3C  C  CH3 
 Cl  C  C  CH3
| | |
Cl Cl CH3
3.
Chloroetone
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10. (3)
H3C  O  CH2  Br
4. (Amide does not give Iodoform
test) For SN1 :
7. (4)

For SN 2 : 1o degree alkyl halide.

 SN1 as well as SN2
On reaction with aq NaOH, the Cl group is
replaced by OH group. 11. (2)
In nucleophilic substitution of haloarene, E W G () Ag2O  H2O  AgOH
Ag O
reactivity of haloarene on ortho & para positions. H3C  CH2 Br 2  H C CH OH
3 2
Moist
opt (4) is correct (3EWG group at ortho & para
positions) 12. (3)
8. (4) Dry
 H3C  CH2  Br  H3C  CH2  O  CH2  CH3
Ag 2O
(1) CH3  CH2  Cl  H3C  CH2 (3  H)
2AgBr.
(2)
13. (2)

(3)

(4)

In Opt 4, l.p of Cl are in resonance with ring,

leading to partial double bond character. Also
formation of vinyl carbocation is unfavorable as it is
unstable.

9. (2)
NaI in DMSO  polar aprotic solvent
 SN2
o
(1) 3 degree C (2) 1o degree C
o
(3) 2 degree C (4) 1o degree C
Out of 2 & 4, (2) is more stable, as T.S. formed

Nucleophile occupy the opp. Lobe of

unhybridised p orbital of central C atom. Ring being

planar to this p orbital can conjugate easily by
delocalising  e .
Benzyl C is reactive for SN1 as well as SN 2
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14. (2) (SN2 favorable)

H
|
(SN1 unfavorable)
Unstable C
Br /hv
H3C  H 2C  C  CH3 
2  H3C  CH 2  C CH3
| | T.S is also unstable
(SN2 favorable)
CH3 CH3 
Most stable radical H2C  CH  CH2  Cl  H2C  CH  CH2
(8  H)
(stable C )
 T.S is also stable
Br (SN2 favorable)
|
H3C  CH 2  C  CH3 18. (1)
Reactivity of aryl halide   of atoms attached
|
 FCl  Br  I
CH3
Highly  , F pulls e  density from the ring,
2-Bromo 2-methylbutane
activating it towards attack.
15. (3)
19. (3)

; (4) on horizontal : (S) conf.

Racemisation)  Retention + Inversion
S  S +R
(Minor) (Major) Resonance stabilised
(Due to less steric
hindrance) 20. (2)

16. (1, 2, 3, 4)
Rate of SN2
 Conc of Nucleophile NaOH (excess)



 Cone of substrate
(Cl is para to NO2.)
 Nature of L.G.
 Nature of solvent.

17. (1, 3)

H2C  CH  Cl  H2C  CH (SN1 unfavorable)
Unstable C
T.S is also not stable (sp.C)
(SN2 unfavorable)

Ph  CH2  Cl  Ph  CH 2 (SN1 favorable)
(Stable C )
T.S is also stable
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(C)

(C  P)
(D)

Br
|
H3C  C  CH3  H3C  C  CH3  H3C  C  CH 2
EtOH
 , E1
| | |
CH3 CH3 CH3

(3° alkyl halide) (9  H)

D  P,Q
21. (1)
A  P,R; B  P,Q; C  P; D  P,Q 22. (1)
alc. KOH
(A) F3C  CHCl2 
E1 C,B
 F2C  CCl2
(many E W G elimination of H & F (A)
Group are present) ( – H)

(B)
(very acidic H)

(A  P,R)
(BP )

(B) (C)

(B  P,Q)

(D)
A  Q, B  P, C  S, D  R
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23. (5) 25. (6)

Alkyl halides do not participate in SNi reactions
alkyl halides can give SN1 ,SN2 , E1, E2 , E1 C.B
6 1  5

24. (6)
R  OH  RX
NaBr, NaCl, NaI are non acidic halides hence
alcohols can’t react with them as they require acidic
=6
halides ;

X
R  OH2 
 R  X  H2O 9  3  6

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