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ORGANIC CHEMISTRY

ALKYL HALIDE
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1
1. Which alkyl halide will react fastest with aqueous ethanol ?
(A) (CH3)3C – Br (B) (CH3)3C – Cl
(C) (CH3)2CH – Br (D) CH3 – CH2 – CH2 – Br

2. When the concentration of alkyl halide is tripled and the concentration of OH¯ ion is reduced to
half, the rate of SN2 reaction increases by:
(A) 3 times (B) 2 times (C) 1.5 times (D) 6 times

3. An SN 2 reaction at an asymmetric carbon of a compound always gives:

(A) an enantiomer of the substrate
(B) a product with opposite optical rotation
(C) a mixture of diastereomers
(D) a single stereoisomer

4. In the given reaction, CH3CH2 – X + CH3SNa 

The fastest reaction occurs when ‘X’ is -
(A) – OH (B) – F (C) – OCOCF3 (D) OCOCH3

2
5. Which of the following involves an “ SN ” route of reaction:
Na
(A) CH3Cl ether
 (B) CH3MgCl + CH3Cl 

(C) CH3Cl + LiAlH4  (D) All

6. The compound which undergoes fastest reaction with aq. KOH solution is : (SN2)
(A) C 6H5  CH  OCH 3 (B) C 6H5  CH  CH3 (C) C6H5 – CH2 – CH2 – Cl (D) C6H5  CH  CH2  CH3
| | |
Cl Cl Cl

7. The rate of S N1 reaction is fastest with:

(A) (B)

(C) (D)

8. In the following reaction the most probable product will be:

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

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9. In the following reaction :

NaI

Acetone

‘X’ [The structure of ‘X’ can be]

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

10. The following reaction is described as:

NaOH 
 
 

(A) SN1 with racemisation

(B) intramolecular SN2 with walden inversion

(C) intramolecular SN2 with retention of configuration

(D) intermolecular SN1 with recemisation

11. The insecticide chlordane is warmed with dilute NaOH solution for some time. The expected
product would be :

(A) (B)

(C) (D)

12. Which configuation will be adopted by the poduct at cabon atoms marked (1) and (2) respectively
in the given reaction.

Ether
+ CH3 CH2  CH  CH3  
|
(D) Br
(A) D, D (B) D, L (C) L, L (D) L, D

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13. Which of the following will undergo fastest elimination reaction with alcoholic KOH.

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

14. When all-cis isomers of C6H6Cl6 (1, 2, 3, 4, 5, 6 - Hexachlorocyclohexane) is heated with alc.
KOH, the most probable product is :

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

15. The most probable product in the following reaction is :

Trans

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

16. Which product(s) will be formed in the following reaction :

alc . KOH
  



(A) No reaction (B) Trans alkene (C) cis alkene (D) cis + trans alkene

17. What will be the major product of the following reaction

CH3 CH3
| | CH OH, 30C
3
CH3  C  C  CH  CH3    
| | |
H CH3 Br

CH3 CH3 CH3 CH3 CH3 CH3

| | | | | |
(A) CH3  C  C  C  CH3 (B) CH3  C  C  CH  CH3
| | |
OCH3 H H

CH3 CH3 CH3 CH3 CH3

| | | | |
(C) CH3  C  C  C  CH3 (D) CH3  C  C  CH  CH2
| | | | |
H OCH3 H H CH3

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18. Which of the following reaction will undergo an elimination reaction and an alkene will be formed in
the products.

(A) Zn dust,  (B)

   


alc. KOH,  conc H SO , 

(C)     (D)   2 
4


19. When (1R, 2R)-1, 2-dibromo-1, 2-diphenyl ethane is treated with alcoholic solution of KOH, the
most probable product would be :
(A) trans-1, 2-diphenyl ethene (B) A mixture of cis, trans alkenyl bromide
(C) cis-alkenyl bromide (D) trans-alkenyl bromide

20. Which of the following products is formed when m-bromochlorobenzene is treated with magne-
sium in the presence of ether ?

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

21. The end product Y of the reaction is :

 H O
C2H5MgBr + S  X 3   Y
(A) C2H6 (B) C2H5SMgBr (C) C2H5SH (D) none of these

Answers
E X E RCI SE -1
1. A 2. C 3. D 4. C

5. D 6. A 7. A 8. B

9. A 10. B 11. D 12. B

13. A 14. B 15. C 16. C

17. C 18. B 19. D 20. A

21. C

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1. Predict the compound in each pair that will undergo the SN2 reaction faster.
2
(a) (i) (ii) (b) (i) (ii)

(c) (i) (ii) (d) (i) (ii)

(e) (i) (ii) (f) (i) (ii)

2. Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more
rapidly.
(a) (i) (CH3CH2)2CH – Cl (ii) (CH3)3C – Cl (b) (i) (ii)

(c) (i) (ii) (d) (i) (ii)

(e) (i) (ii) (f) (i) (ii)

3. The correct decreasing order of relative reactivity of the following bromides towards hot aqueous
KOH solution is:
(I) CH3 – CH2 – Br (II) CH3 – CH2 – CH2 – Br

(III) OH – CH2 – CH2 – Br (IV) CH3 – – CH2 – Br

(A) I > III > II > IV (B) I > II > III > IV (C) I > II > IV > III (D) III > I > II > IV

4. For a given alkyl halide, the ease of formation of Grignard reagent is:
(A) RI > RBr > RCl (B) RI > RBr < RCl
(C) RI < RBr < RCl (D) RI > RCl > RBr

5. The correct order of reactivity of the following halides for bimolecular elimination is :
(I) (CH3)2 CH – CHI – CH3 (II) (CH3)2CH – CH2 – CH2 – I

(III) CH3 – CH2 – CHI – CH3 (IV) (CH3 ) 2 C  CH2  CH3

|
I

(A) II > III > I > IV (B) III > II > I > IV (C) I > II > III > IV (D) IV > I > III > I

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6. The relative reactivity of following halides towards ethanol follows the order:
(I) CH3 – – Cl (II) CH3CH2Cl (III) CH3 – O – CH2 – Cl (IV) C6H5– CH2 – Cl

(A) II > IV > III > I (B) I > IV > III > II (C) IV > III > II > I (D) I > III > IV > II

7. The increasing order of reactivity of the following isomeric halides with alcoholic AgNO3 is :

(I) C6H5 – CH = CH – CH2 – CH2 – Cl (II) C 6H5  CH  CH  CH  CH3

|
Cl

CH3
|
(III) C 6H5  C  CH  CH2  CH3 C H
(IV) 6 5  C  CH  CH2
| |
Cl Cl

(A) III < IV < II < I (B) I < III < IV < II (C) III < I < II < IV (D) I < II < IV < III

8. Rate of S N1 reaction is :

(I) (II) (III) (IV)

(A) IV > I > III > II (B) II > III > I > IV (C) I > III > II > IV (D) IV > II > III > I

9. Rate of reaction with aqueous AgOH solution follows the order.

(I) (II) (III) (IV)

(A) II > IV > I > III (B) IV > II > I > III (C) III > II > IV > I (D) I > IV > II > III

10. In the following compound, arrange the reactivity of different chlorine atoms towards NaSH in
decreasing order in non aqueous solvent.

(A) II > IV > I > III (B) I > II > III > IV
(C) II > IV > I > III (D) II > III > I > IV

11. The reactivity order of CH3MgBr with the following reagents is

(I) PhOH (II) CH3CHO (III) R–C  CH (IV) CH3  C  Cl

||
O
(A) I > III > II > IV (B) I > II > III > IV
(C) IV > I > III > II (D) I > III > IV > II

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Correct decreasing order of reactivity towards SN2 reaction : Q. 12 to Q. 18

I II III IV
12. CH3Cl CH3CH2Cl CH3CH2–CH2–Cl CH3CHClCH3
(A) I > II > III > IV (B) III > II > I > IV (C) IV > III > I > II (D) None

13. CH3CH2 CH2Cl CH3 CH2CH2Cl CH3CH2CH2CH2Cl CH3CH2CH2

(A) IV > I > II > III (B) III > II > I > IV (C) IV > I > III > II (D) II > I > IV > III

CH3 CH3
CH3
| | |
14. CH3  C  CH2  Cl CH3 – C – Cl CH3  C  Cl CH3 – CH2 – Cl
| | |
CH3 CH3 H
(A) II > III > I > IV (B) II > I > IV > III (C) IV > III > I > II (D) I > III > II > I

15. Br – CH2 – CH2 – Br N  C – CH2 – Br CH3  CH  CH3 CH3 – CH2 – Br

|
Br
(A) II > I > IV > III (B) II > III > I > IV (C) II > I > III > IV (D) IV > I > II > III
16. CH3CH2Cl CH2 = CH – CH2Cl CH3Cl CH2 = CHCl
(A) II > III > I > IV (B) II > I > IV > III (C) IV > III > II > I (D) none

17. CH3–O–CH2–Cl H  C  CH2  Cl CH3–CH2–Cl CH3–Cl

||
O

(A) IV > III > II > I (B) II > III > I > IV (C) II > I > IV > III (D) none

18. HO–H2C–CH2–Cl CH3–CH2–Cl CH3–CH2–CH2–Cl CH3  C  Cl

||
O
(A) IV > I > II > III (B) IV > I > III > II (C) II > I > IV > III (D) II > III > I > IV
Arrange the following in decreasing order of reactivity towards SN1 reaction : (19 to 29)
I II III IV
19. CH3Cl CH3CH2Cl CH3CH2–CH2–Cl CH3CHClCH3
(A) IV > I > II > III (B) I > II > III > IV (C) IV > III > II > I (D) III > IV > I > II

CH3 CH3 CH3

| | |
20. CH3–CH2–CH2–Cl CH3  CH  CH2  Cl CH3  C  CH2  Cl CH3  C  Cl
| |
CH3 CH3

(A) IV > III > II > I (B) I > II > III > IV (C) III > II > I > IV (D) IV > I > II > III

21. CH3CH2 CH2Cl CH3 CH2CH2Cl CH3CH2CH2CH2Cl CH3CH2CH2

(A) IV > III > II > I (B) IV > I > II > III (C) I > II > III > IV (D) IV > II > I > III

22.

(A) I > II > III > IV (B) IV > III > II > I (C) IV > II > I > III (D) IV > I > II > III

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I II III IV

23.

(A) IV > III > I > II (B) IV > I > II > III (C) I > II > III > IV (D) II > I > III > IV

24.

(A) III > II > I > IV (B) IV > I > III > II (C) I > II > III > IV (D) IV > III > II > I
CH3
|
25. CH2=CH–CH2–Cl CH2  CH  CH  Cl CH3–CH=CH–CH2–Cl CH3  C  CH  CH3
|
Cl
(A) IV > III > I > II (B) II > III > I > IV (C) I > II > IV > III (D) III > II > I > IV
CH3 O
| ||
26. C 6H5  C  Br CH3  C  CH  Br (CH3)2CHBr
| |
CH3 CH3
(A) II > I > IV > III (B) I > II > IV > III (C) II > IV > I > III (D) III > IV > I > II

27. (C6H5)2CHCl CH2 = CH CH2Cl C6H5 CH2Cl

(A) I > III > II > IV (B) IV > III > II > I (C) II > IV > III > I (D) I > II > III > IV

28.
(A) I > II > III (B) II > III > I (C) II > I > III (D) III > II > I

29.

(A) I > II > III > IV (B) IV > III > II > I (C) II > III > I > IV (D) IV > II > III > I

Answers
E X E RCI SE -2
1. (a) (i) > (ii) (b) (ii) > (i) (c) (ii) > (i)
(d) (ii) > (i) (e) (ii) > (i) (f) (i) > (ii)
2. (a) (ii) > (i) (b) (ii) > (i) (c) (i) > (ii)
(d) (ii) > (i) (e) (ii) > (i) (f) (ii) > (i)
3. D 4. A 5. D 6. D 7. C 8. D 9. B
10. C 11. D 12. A 13. B 14. C 15. A 16. A
17. C 18. A 19. C 20. A 21. B 22. D 23. C
24. A 25. B 26. A 27. C 28. C 29. D

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The major productof the following reactions (Q.1 - Q.4)

3
1. + 

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

2. CH3 I + 

iodomethane
(methyl iodide)

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

3. CH3 CH2CH2 CH2CH2Br + 

1  bromopen tan e
(A) CH3 – CH2 – CH2 – CH2 – CH3 (B) CH3 – CH2 – CH2 – CH2 – CH2 – SH

(C) CH3  CH2  CH  CH2  CH3 (D) CH3  CH  CH2  CH2  CH3
| |
SH SH

4. CH3 CH 2CH 2CH 2Cl + : NH3 

1  chlorobu tane ammonia
(n  butyl chloride ) ( excess )

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

|
NH2

(C) CH3  CH2  CH  CH3 (D) CH3 – CH2 – CH2 – CH2 – NH2
|
Cl

Predict the products of the following SN2 reactions (Q. 5 - Q. 12)

3 CH CH OH
5. CH3CH2ONa + CH3CH2Cl   2
(A) CH3 – CH2 – CH2 – O – CH3 (B) CH3 – CH2 – O – CH2 – CH3

(C) CH3 – CH2 – CH2 – CH2 – OH (D) CH3  CH2  CH  CH3

|
OH

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acetone
6. + NaCN  


(A) (B)

(C) (D)

7. 

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

acetone
8. CH3(CH2)8CH2Cl + NaI  


(A) CH3  (CH2 )7  CH  CH3 (B) CH3  (CH2 )8  CH2  I

|
I
(C) CH3 – (CH2)8 – CH3 (D) CH3 – (CH2)7 – CH = CH2

9. + CH3I 

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

10. (CH3 )3 C  CH2CH2Br + NH3 

excess

(A) (B) (CH3)3C – CH2 – CH2 – NH2

(C) (CH3)3C – CH2 – CH2 – CH3 (D) [(CH3)3C – CH2 – CH2]4N

11. + NaOH 

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

NaOH
12.  
CH3OH

(A) (B)

(C) (D)

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13. ether
+ Mg  

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

Li CuI CH3I
14. (CH3)2 CHCH2I    

(A) (CH3)2CH – CH3 (B) (CH3)2CH – CH2 – CH3
(C) (CH3)2CH – CH2 – CH2I (D) None of these

( C2H5 )2 CuLi
15. CH3  CH2  CH  C  CH3    
|
Br

(A) CH3  CH2  CH  C  CH3 (B) CH3  CH2  CH  C  CH3 + C2H5Cl + LiBr
| |
C 2H5 C 2H5

(C) CH3 – CH2 – CH = CH – CH3 + 2C2H5Cu (D) CH3  CH2  CH  C  CH3  LiBr
|
C2H5
( i)
Et 2O
16. + (CH3)2CH Mg Br  
( ii) H O 2

(A) CH3 – (CH2)4 – CH2 – OH (B) CH3  CH  CH  CH  CH3

|
C 2H5

(C) (D) CH3  CH  CH2  CH3

|
OH

17. C6H5COOH + CH3MgI 

(A) C6H5COOMgI (B) CH4 (C) Both A & B (D) none

2
HO
18. 2-Butanone + Ethyl Magnesium bromide 

H CH3
| |
(A) CH3  C  CH2  CH3 (B) CH3  C  CH2  CH3
| |
OH OH

C 2H5
|
(C) CH3  C  CH2  CH3 (D) All of these
|
OH

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The major product of the following reactions (Q.19 - Q.23)

19. CH3CH2CH2 – Br + CH3O¯

(A) CH3 – CH2 – CH2 – OH & SN2 (B) CH3 – CH2 – CH2 – O – CH3 & SN2
(C) CH3 – CH2 – CH2 – O – SN1 (D) CH3 – CH2 – O – CH2 – CH3 & E2

50 C
20. CH3 – CH2 – CH2 – Br + (CH3)3CO¯  
(CH3 )3 COH
(A) CH3 – CH2 – CH3 & SN2 (B) CH3 – CH = CH2 & SN1
(C) CH3 – CH = CH2 & E2 (D) None

21.

CH3
|
(A) CH3 – CH2 – CH2 – CH2 – SH & SN1 (B) CH3  C  SH & SN2
|
H

(C) & E2 (D) & SN2

22. (CH3CH2)3 C – Br + OH¯

CH2  CH3
|
(A) & E2 (B) CH3  C  CH3 & SN2
|
CH2  CH3
(C) CH3 – CH = CH – C2H5 (D) None

23. (CH3CH2)3 C – Br

(A) CH3OC (CH2CH3)3 & SN2 (B) CH3OCH (CH2CH3)2 & SN1
(C) CH3OC (CH2CH3)3 & SN1 (D) None

Answers
E X E RCI SE -3
1. A 2. C 3. B 4. D
5. B 6. A 7. D 8. B
9. C 10. A 11. C 12. B
13. D 14. B 15. B 16. C
17. C 18. C 19. B 20. C
21. D 22. A 23. C

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Which of the following is the correct option of reagents for the given conversion :
4
(Q.1 - Q.6)
1. Propane  2-Iodopropane
(A) I2 / h (B) NaI / acetone
(C) F2 / h, NaI / acetone (D) Br2 / h, NaI / acetone

2. CH3 – CH2 – CH3  CH3 – C  C – H

(A) Br2 / h, alc. / KOH, Br2 / h, NaNH2 (B) Br2 / CCl4, alc. / KOH, Br2 / h, NaNH2
(C) Br2 / h, NaNH2 (D) Br2 / h, aq. KOH, Br2 / h, NaNH2

CH3
|
3. CH3 – CH2 – CH3  CH3  C  D
|
H
(A) Br2 / h, NaNH2, D2 / Ni
(B) Br2 / h, Mg / Et2O, D2O
(C) Br2 / h, Mg / Et2O, CH3 – Br, Br2 / h, D2O
(D) Br2 / h, Mg / Et2O, C2H5Br, Br2 / h, D2O

CH3
|
4. CH4  CH3  CH  COOH
(A) Br2 / h, CH3CH2MgCl, Br2 / h, HCOOH
(B) Cl2 / h, CH3CH2MgCl, Br2 / h, KCN, H3O+
(C) Br2 / h, CH3CH2MgCl, Br2 / h, NaNH2, HCN, H3O+
(D) Cl2 / h, CH3MgBr, Br2 / h, CH3 – COOH

O
||
5.  OHC  (CH 2 ) 3  C  CH3

(A) Mg / Et2O, CH3Cl, Br2 / h, alc. KOH, hot KMnO4

(B) OH¯, H2SO4 / , O3 / Zn, H2O
(C) CH3MgBr, Br2 / h, alc. KOH, hot KMnO4
(D) Mg / Et2O, CH3Cl, Br2 / h, alc. KOH, O3

6. 

(A) alc. KOH, Br2 / CCl4, NaNH2, Na / liq NH3 , Br2 / CCl4
(B) alc. KOH, Br2 / CCl4, NaNH2, H2 / Pd-CaCO3, Br2 / CCl4
(C) alc. KOH, Br2 / CCl4
(D) NaNH2, cold KMnO4, excess HBr

Answers
E X E RCI SE -4
1. D 2. A 3. B 4. B 5. D 6. A

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5
Read the following questions and choose :
(A) If both Assertion and Reason are true and the Reason is correct explanation of the
Assertion.
(B) If both Assertion and Reason are true, but Reason is not correct explanation of the
Assertion.
(C) If Assertion is true, but Reason is false.
(D) If Assertion is false, but the Reason is true.

1. Assertion : The SN 2 reaction of neopentyl bromide, (CH3)3CCH2Br, with sodium ethoxide,

Na+(OCH2CH3)¯, proceeds about 0.00001 times as fast as the reaction of bromoethane.
Reason : The bulky groups present at -position in neopentyl bromide exert a strong steric
hinderance to the approaching nucleophile.
(A) A (B) B (C) C (D) D

2. Assertion : The major product of the reaction of methylenecyclohexane with N-bromosuccinimide

is 1-(bromomethyl)cyclohexene.
Reason : In the reaction of methylenecyclohexane with N-bromosuccinimide a more stable
secondary as well as allylic radical intermediate is formed which gives 2-Bromo-1-
methylenecyclohexne
(A) A (B) B (C) C (D) D

3. Assertion : Aryl halides are less reactive than alkyl halides towards nucleophilic reagents.
Reason : In aryl halides halogens create negative charge centres to the ortho & para position of
benzene ring which favours electrophilic substitution reactio but not the nucleophilic
substitution reaction.
(A) A (B) B (C) C (D) D

4. Assertion : The trans isomer of 2-chlorocyclohexanol is hydrolysed with many times faster rate
than the cis isomer on heating with NaOH solution.

NaOH
 


Reason : The trans isomer causes less steric crowding in the SN2 reaction to the nucleophile.
(A) A (B) B (C) C (D) D

5. Assertion : CH3CH2CH2CH2Cl reacts with 0.01 M NaCN in ethanol to yield primarily CH3
CH2CH2CH2CN whereas under the same conditions (CH3)3CCl reacts to give primarily (CH3)3
COCH2CH3.
Reason : The first reaction is a SN2 reaction in which CN¯ is a strong nucleophile, in the second
reaction the reactant forms a carbocation intermediate which is solvent stabilised by C2H5OH &
SN1 reaction takes place.
(A) A (B) B (C) C (D) D

6. Assertion : Rate of hydrolysis of (CH3)3C – F increases under strongly acidic conditions.

Reason : It is an example of electrophilic catalysis. F¯ is a poor leaving group H-bonding with
strong acid encourages its departure.
(A) A (B) B (C) C (D) D

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7. Assertion : Hydrolysis of n-Butylchloride in aqueous ethanol is accelerated in presence of NaI.

Reason : In all SN1 reactions the reactivity increases in a polar medium in which the carbocation
is solvent stabilised.
(A) A (B) B (C) C (D) D

8. Assertion : When the alkyl bromides were subjected to hydrolysis in a mixture of ethanol &
water (80% C2H5OH, 20% H2O) at 55ºC, the rates of reaction showed the following order :
(CH3)3C – Br > CH3 – Br > CH3CH2 – Br > (CH3)2 CH – Br
Reason : In SN1 reaction the reactivity order of different alkanes is R3CH > R2CH2 > RCH3 > CH4
since the carbocation produced in the rate determining step has the stability order as
R3C+ > R2CH+ > RCH2+ > CH3+ .
(A) A (B) B (C) C (D) D

9. Assertion: In contrast to SN2 reactions,SN1 reactions show relatively little nucleophile selectivity.
Reason : The reactivity of nucleophile is less in SN1 as compared to SN2.
(A) A (B) B (C) C (D) D

10. Assertion: CH3CH2 – CH2 – CH2 – Cl reacts with 0.01 M NaCN in ethanol to yield primarily
CH3 – CH2 – CH2 – CH2 – CN whereas under the same conditions (CH3)3 C – Cl reacts to give
primarily (CH3)3 COCH2–CH3.
Reason : With different alkyl halide the nucleophilicity of nucleophiles changes.
(A) A (B) B (C) C (D) D

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Answers
EXERCISE - 5
1. A

2. B
Explanation :
The intermediate allylic radical reacts at the more accesible site and gives the more
highly substituted double bond.

NBS
   

3. B
Explanation :
due to : Halogen atoms has double bond character and p-orbital of benzene ring repels the nucleophile
therefore SN2 reactivity is also very low.

4. C
Explanation :

NaOH NGP
   


does not have NGP..

(NGP = Neighboring group participation or anchimeric assistance)

5. A
Explanation :

NaCN C H OH
CH3CH2CH2CH2Cl   2 5  CH3CH2CH2CH2CN
SN2

NaCN C H OH
   2 5 
SN1

ionises in C2H5OH and solvolysis (ethanolysis) takes place. while in

CH3CH2CH2CH2Cl, CN¯ (being strong anionic nucleophile) attacks and bimolecular substitution
takes place.

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6. A
Explanation :

CH3 CH3 CH3

|  1|   |
H3 C  C  F + H  O  H  H3 C  C.....F .....H  O  H  H3 C  C  OH + HF + H+
| | | | |
CH3 H CH3 H CH3

7. B
Explanation :
NaI
CH3 – CH2 – CH2 – CH2 – Cl  CH3 – CH2 – CH2 – CH2 – I + NaCl
CH3 – CH2 – CH2 – CH2 – OH

is a good nucleophile as well as a good leaving group.

8. B
Explanation :
(CH3)3 C – Br hydrolyses by SN1 route, so due to ionisation reaction it is fastest.
CH3 – Br will hydrolyse by SN2, and rate of SN2 will be faster in CH3 Br than CH3 – CH2 – Br.
(CH3)2 CH – Br will be hydrolysed by mixed mechanism (SN1 + SN2) and both routes will have
moderate speed.

9. B
Explanation :
In SN1 reactions the first step is slow ionisation of alkyl halide. This is the rate determining step so
the rate of overall reaction depends upon nature and concentration of alkyl halide only. There is no
direct dependence of rate on nature or concentration of nucleophile.

10. C
Explanation :

NaCN C H OH
CH3 – CH2 – CH2 – CH2 – Cl   2 5  CH3 – CH2 – CH2 – CH2 – CN
SN2

NaCN C H OH
   2 5 
SN1

ionises in C2H5OH and solvolysis (ethanolysis) takes place. while in

CH3 – CH2 – CH2 – CH2 – Cl, CN¯ (being strong anionic nucleophile) attacks and bimolecular
substitution takes place.

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Identify the unknown compound/s or reagent/s in the following reactions : (Q.1 - Q.16)
CH3
|
NaI, Acetone
1. CH3  C  CH  CH2   (X) (Allylic SN2)
|
Br

CH3 CH3
| |
(a) CH2  C  CH  CH2 (b) CH3  C  CH  CH2
|
I
CH3 CH3
| |
(c) CH3  C  CH  CH2 I (d) CH2  C  CH  CH3
|
I

NaOH CH2 CHCH2 Br

2.  (X)
      

(a) (b)

(c) (d)

3. NaOH, 
   (X)

(a) (b)

(c) (d)

4. X (major)

(a) (b)

(c) (d)

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H O, Ag
2
5.    W (major product)

(a) (b) (c) (d)

6. ‘X’

(a) (b)

(c) (d)

7. CH22 + 2Na+ CH¯

(a) HOOC – CH2 – CH2 – CH2 – COOH (b)

(c) (d)

Cl
8. V (C6H14) 
2
 W + X + Y (Monochlorides)
Sunlight


( CH3 )3 CO ¯ K
W or X    Z (C6H12)
( CH3 )3 COH

C H5OH  KOH
Y 2    No reaction.

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CH3
|
(a) V : CH3 – CH2 – CH2 – CH2 – CH2 – CH3 (b) V : CH  C  CH  CH
3 2 3
|
CH3

CH3
|
(c) Y : Cl  CH2  C  CH2  CH3 (d) Y : Cl – CH2 – CH2 – CH2 – CH2 – CH3
|
CH3

Br / h alc. KOH
9. 2  
 (X)

(a) (b) (c) (d)

C H O ¯K   C H OH
2 5 2 5
10.     
 X

(a) (b)

(c) (d)

CH MgBr
3 CH MgBr
3 CH MgBr
11. CH2  COOC2H5 3
   X    Y    Z
|
CH2  C  CH2  CH2  OH
||
O

CH2  COCH3 CH2  COOC2H5

| |
(a) Z : CH2  C(CH3 )  CH2 CH2  OMgBr (b) Y : CH2  C(CH3 )  CH2  CH2  OMgBr
| |
OMgBr OMgBr

CH2  COCH3 CH2  COCH3

| |
(c) Y : CH2  C  CH2  CH2  OMgBr (d) X : CH2  C  CH2  CH2  OH
|| ||
O O

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( i) ( C H ) O
12. CH3 – CH2 – CH2 – CH2 – MgBr + (X)  2 
5 2

 n – C7H15OH
( ii) H3O

(a) Br – CH2 – CH2 – CH2 – OH (b)

(c) H2O+ – CH2 – CH2 – CH2 – OH (d) TsO – CH2 – CH2 – CH2 – OH

(1) Li Y
13. CH3  CH  CH2  Br     2, 7-Dimethyloctane
( 2) CuI X
|
CH3

(a) X : CH3  CH  CH2  CuLi (b) X :  CH3  CH  CH2   CuLi

|  | 
CH3  CH 
 3 2

(c) Y : Br  CH2  CH 2  CH2  CH  CH3 (d) Y : CH3  CH2  CH2  CH  CH2  Br

| |
CH3 CH3

14. W + CH3–CH2–CH2–Br 


(a) (b) (c) (d)

15. W + (CH3)2CuLi 


(a) (b) (c) (d)

16. (CH3CH2)2CuLi + W 


(a) (b) (c) (d)

17. A monoprotic acid ‘A’ on reduction with red P + HI gives an alkane ‘B’ which on reaction with
Cl2 / h gives a mixture of two isomeric monochloro alkanes. ‘B’ can be prepared by catalytic
hydrogenation of a hydrocarbon ‘C’ whose one mole on reaction with excess C2H5MgI gives
4 moles of ethane. Identify the incorrect option / options.
(a) A is an acid (b) B is an alkane (c) C is an alkene (d) C is an alkyne
18. Optically active compound (A) C4H8Br2 is treated with CH3ONa / CH3OH to obtain compound (B).
C4H7Br. ‘B’ reacts with Gilman reagent of n-butyl iodide and gives ‘C’ (C8H16). ‘C’ on reductive
ozonolysis gives D and E. D gives red precipitate with fehling solution but E does not. Both
respond positively towards I2 / NaOH solution. Identify A.

CH3 CH3
| |
(a) CH2  CH2  C  H (b) CH3  CH2  C  Br
| | |
Br Br Br

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Br CH3 CH3
| | |
(c) CH3  C  C  H (d) CH3  CH  C  H
| | | |
Br H Br Br

19. One mole of compound A (C3H8O3) is treated with excess of CH3MgBr in ether. The liberated gas
measured 67.2 litres at S.T.P. Identify the structure of A.

CH3 CH3
| |
CH2  OH O CHO
O
| | |
(a) CH  OH (b) | (c) (d) CHOH
CH2 H CO H
| | |
|
CH2  OH O CHO
O
| |
CH3 CH3

20. A primary alkyl halide (A), C4H9Br, reacted with alcoholic KOH to give compound (B).Compound
(B) reacted with hydrogen bromide to give (C), an isomer of (A). When (A) was treated with
sodium, it gave a compound (D), C8H18, which was different from the compound produced when
n-butyl bromide was reacted with sodium. The structural formula of A is.

CH3 CH3
| |
(a) CH3  C  CH3 (b) CH3  C  CH2  Br
| |
Br H

(c) CH3 – CH2 – CH2 – CH2 – Br (d) CH3  CH2  CH  CH3

|
Br
21. When 1-chloromethyl-4-methyl-1, 3-cyclopentadiene (A) is treated with H 2O / Ag+, three
isomeric alcohols are obtained. Then which is not among these isomeric alcohols.

(a) (b) (c) (d)

22. An organic compound (A), C7H15Cl on treatment with alcoholic caustic potash gives a hydrocarbon
(B) C7H14.(B) on treatment with ozone and subsequent hydrolysis gives acetone and
butyraldehyde. What (B) ?
H
|
(a) H3 C  C  C  C  CH3 (b) H3 C  C  CHCH2CH2CH3
| | | |
CH3H H CH3

H
|
(c) H3 C  C  CH2  CH  CH2 (d) H3 C  C  CH2  CH2  CH3
| |
CH3 CH3

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23. Treatment of 2-bromobutane with hot alcoholic KOH gives a mixture of three isomeric butenes (A),
(B) and (C). Ozonolysis of the minor product (A), gives formaldehyde and another aldehyde in
equimolar amounts. Both (B) and (C) gave the same single product (D) on ozonolysis. What is the
structural formula of (D) ?
O
||
HC  O CH  C  CH3
(a) CH3 CH2C  O (b) (c) CH3  C  O (d) 3
|
| |
H
H H

24. The reaction of 2-chloro-2-methyl-1-phenylpropane with methanol yields a mixture composed of a

substitution product A (54%) and two elimination products, B (27%) and C (19%). which structure
is written with incorrect percentage.
CH3
|
(a) (b) Ph  CH2  C  CH2 ( 27%)

CH3
|
(c) Ph  CH  C  CH3 (27%) (d) PhCH 2  C  CH2 (19%)
|
CH3

25. Compound X is optically inactive and has the formula C16H16Br2. On treatment with strong base, X
gives hydrocarbon Y, C16H14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a
palladium catalyst and reacts with ozone to give two fragments. One fragment, Z, is an aldehyde
with formula C7H6O. The other fragment is glyoxal, (CHO)2. suggest structure for X.
(a) Ph  CH2  CH  CH  CH2  Ph (b) Br  CH2  CH  CH  CH2  Br
| | | |
Br Br Ph Ph

Ph
|
(c) Ph  CH  CH2  CH2  CH  Ph (d) Ph  C  CH  CH  CH  Br
2 2
| | | |
Br Br H Br
26. Organic compound (A) C5H11Cl on treatment with sodamide form compound (B). Compound (B)
reacts with dilute acid to form (C), C5H12O. When compound (C) is heated with Al2O3 ,it forms (D)
which is isomeric to (B). Combined ozonolysis of (B) and (D) forms four compounds two of which
reduces Tollen’s reagent and three of which show haloform reaction. What will be the nature of (C).
(a) A primary alcohol (b) A secondary alcohol
(c) A tertiary alcohol (d) An ether

27. The alkyl halide C4H9Cl (A) reacts with alcoholic KOH and gives alkene (B) which reacts with
bromine to form a dibromide (C). (C) is transformed with sodamide to a gas (D) which forms a
precipitate with ammonical silver nitrate solution. Give the structures (C).
(a) CH3 – CH2 – CH(Br)CH – Br (b) CH3  CH  CH2  CH2
| |
Br Br

(c) CH2  CH2  CH2  CH2 (d) CH3 – CH2 – CH2 – CHBr2
| |
Br Br

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28. Five isomeric alkyl halides (C6H13Cl) produce the same alkane (A) (C6H14) on reduction with Zn/Cu
couple. Identify (A).

CH3
CH3
|
|
(a) CH3  CH2  C  CH3 (b) H C  CH  CH  CH  CH
3 2 2 3
|
H

CH3 CH3
| |
(c) H3 C  CH2  CH  CH2  CH3 (d) CH3  CH2  C  CH3
|
CH3
29. A chloroderivative (X) on treatment with Zn-Cu couple in ethanol gives a hydrocarbon (Y). When (X)
is dissolved in ether and treated with sodium, 2, 2, 5, 5 - tetramethylhexane is obtained. Identify
how many different types of hydrogen atoms are present in Y.
(a) 1 (b) 2
(c) 3 (d) 4

30. An alkane C6H14 (A) on chlorination at 300° gives a mixture of 4 monochlorinated derivative B, C, D
and E. Two of these (C, D) derivatives give the same stable alkene (F) on dehydrohalogenation.
The other two alkyl halides (B, E) give alkenes (G) and (H) respectively. Which on ozonolysis give
methanal as the common product. (H) gives a ketone while (G) gives an aldehyde. Give structure
of (H).

CH3
CH3
|
|
(a) CH 2  CH  C  CH2  CH3 (b) CH3  CH  C  CH2  CH3
|
H

CH2 CH2
|| ||
(c) CH  CH  C  CH  CH (d) CH  C  CH  CH  CH
3 2 2 3 3 2 2 3

31. A compound A has molecular formula C6H13Br. When it is treated with magnesium metal in ether,
dilute acid produces the compound n–hexane as a product.When compound A is reacted with
sodium metal in ether, the product is 4, 5 –diethyloctane .From the above information deduce the
structural formula of (A).
(a) CH3 – CH2 – CH2 – CH2 – CH2 – CH2 – Br (b) CH3 – CH2 – CH2 – CH2 – CHBr – CH3

CH3
|
(c) CH3 – CH2 – CH2 – CH(Br)CH2 – CH3 (d) CH3  CH2  C  CH2  CH3
|
Br

32. The D-isomer of an optically active organic compound A (C8H17Br) on reaction with NaI in
acetone produced another optically pure compound B (C8H17I). A on hydrolysis with NaOH solution
in H2O (20%) + Acetone (80%) mainly produced optically active compound C (C8H18O). B also on
hydrolysis under similar conditions produced another compound (D). Both A and B on reaction
with CH3MgBr in ether produced 2-methyloctane. Indicate how C and D are related ?
(a) Identical (b) Enantionmers
(c) Diastereomers (d) Structural isomers

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33. A mixture of isobutane and iso butene is catalytically hydrogenated and the entire alkane is
monobrominated in the presence of light at 1270C, which exclusive product would be formed?

H Br
| |
(a) CH  C  CH (b) CH3  C  CH3
2 3
| | |
Br CH3 CH3

CH3  CH2
(c) | (d) CH3 – CH2 – CHBr – CH3
Br  CH2  CH 2

34. (W) and (X) are optically active isomers of C5H9Cl.(W) on treatment with one mol of H2 is converted
to an optically inactive compounds (Y), but (X) gives an optically active compounds (Z) under the
same conditions. Give configurations of (W), in fischer projections.

(a) (b)

(c) (d)

35. An alkyl halide (A) C4H9Cl on reaction with CH3MgCl gives on alkene (B) (C4H8) as major
product with CH4. Only one dichloro derivative can be obtained by C4H9Cl. Give structure of B.

(a) CH2 = CH – CH2 – CH3 (b)

(c) (d) CH3  C  CH2

|
CH3

36. An alkyl halide (A) on reaction with Mg in ether gives a Grignard reagnet (B). B on reaction with
C2H5Cl gives C5H12 (C). Monochlorination of (C) gives 4 structures. Out of which how many
structures contain one chiral carbon ?
(a) 1 (b) 2
(c) 3 (d) 4

37. One mole of hydrocarbon C9H12 (A) on reaction with CH3MgX gives 2 moles of CH4. On
complete hydrogenation A gives C9H20 (B). B is optically inactive & on monohalogenation it gives
only 2 structurally different monohalo derivatives. Give structures of these derivatives.

CH2  CH3 CH2  CH3

| |
(a) CH3  CH  C  CH2  CH3 (b) CH 2  CH  C  CH2  CH3
| | | |
X CH2  CH3 X CH2  CH3

CH2  CH3 CH2  CH3  X

| |
(c) CH3  C  CH2  CH2  CH2 X (d) CH3  C  CH2  CH2  CH3
| |
CH2  CH3 CH2  CH3

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38. An organic compound P (C5H8O) decolourises Br2 water & Baeyer’s reagent. P does not
responds to 2, 4-DNP but on reaction with PhMgBr, (P) gives 2 moles of benzene. On complete
hydrogenation ‘P’ gives (Q) which on reaction with Luca’s reagent gives immediately white
turbidity. Give possible structure of P.

OH OH
| |
H
(a) 3 C  CH2  C  CH3 H
(b) 2 C  CH  C  CH3
| |
CH3 CH3

OH OH
| |
(c) H  C  C  C  CH3 (d) H  C  C  C  CH2  CH3
| |
CH3 H

Answers
EXERCISE - 6
1. c 2. b 3. c 4. c
5. b 6. d 7. a 8. b, c

9. a 10. c 11. a, b 12. b

13. b, c 14. d 15. a 16. d
17. b 18. c 19. a 20. b

21. a,b 22. b 23. c 24. b

25. c 26. c 27. a 28. b

29. a 30. c 31. c 32. b

33. b 34. c 35. d 36. b

37. a, b 38. c

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CH2CH2Br
CHO

1. ? The final product of the reaction is

CH3

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

2. Which one is correct for the products of the given reaction

(A) only X and Z are formed (B) Z > Y

(C) X > Y (D) Y > X

3. The most polar as well as stable conformation of 1-chloropropane is

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

4. Dehydrohalogenation by a strong base is slowest in.

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

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5. In which case an alkene is formed on reaction with a strong anionic base.

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

6. Which statement is correct for the following reaction, regarding rate, and stereorientation at
C1 and C2 respectively (for the major product)

(A) Very slow, inversion and retention (B) Very fast, inversion and retention
(C) Very fast, retention and retention (D) Very fast inversion and inverstion
7. The correct reactivity order for the following reaction is
NaI / Acetone
RBr    R – I + NaBr 
..
R: CH3 CH 3 CH 2 CH3  O
..  CH2 CH 2  CH

I II III IV
(A) I > II > III > IV (B) III > I > II > IV (C) IV > III > I > II (A) III > IV > I > II

8. The major product of the following reaction is

(A) (B)

(C) (D)

9. The rate of reaction of CH3CH2Br is fastest with

(A) (CH3)3CLi (B) NaNH2 (C) CH3ONa (D) NaOH
10. In which of the following reactions an optically active single product is formed

(A) CH3ONa + (B)

(C) + (D)

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11. Which one is correct for the products of the given reaction

(A) only X and Z are formed (B) Z > Y

(C) X > Y (D) Y > X

12. Read the following question and choose the correct answer :
(A) If both Assertion and Reason are true and the Reason is correct explanation of the
Assertion.
(B) If both Assertion and Reason are true, but Reason is not correct explanation of the Assertion.
(C) If Assertion is true, but Reason is false.
(D) If Assertion is false, but the Reason is true.

Assertion : In the above reaction a mixture of two stereoisomeric products can be formed
Reason : The O O group of the molecule provides anchimeric assistance (neighbouring group
participation) in substitution of so there is retention of configuration at both the asymmetric
carbon atoms.

13. Which one of the following hexachlorocyclohexane is least reactive and which one is most
reactive in E2 reactions with a strong base for dehydrohalogenation.

(A) I least & II most (B) II least & I most

(C) III least & I most (D) III least & II most

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14. Which of the following reaction is not feasible.

CH 3
CH OH
3 CH 3
(A)    +
 OCH 3

(B) +

C H OH
(C) 25 + +


CH3
|
(D) CH3  C  Cl + HC +  O
|
CH3
Section - B (Reading comprehension Q. 15 - 19)
Observe the following reactions and give answers of questions. (Q.13 – Q.17)

CH3
|
CH3  CH2  C  CH2

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15. In Ist reaction the structure of reaction intermediate should be

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

16. Which statement seems to be most appropriate for reaction II.

(A) It is an E1 reaction
(B) The product is a mixture of stereoisomers
(C) is a good nucleophile but a poor base which can cause dehalogenation in vicinal dihalides
(D) It is SN1 reaction at 3° C – Cl bond while SN2 reaction at 1° C – Cl bond.
17. Which of the following structure represents the transition state of slow step of reaction III.

(A) (B)

(C) (D)

18. Which of the reaction (I – VI) involves rearrangement of reaction intermediate.

(A) III only (B) III, V (C) II, III, V (D) I, III, V
19. Planar reactive intermediates are formed in reactions
(A) III, V (B) I, III, V (C) V, VI (D) I, III, V, VI

A nswers
EXERCISE - 7
1. D 2. D 3. C
4. (C)
All ‘Cl’ are having trans orientation with respect to each other. So the required anti orientation of
 – H and ‘Cl’ is not available.
5. (B) H and Cl are in anti position to each other only in case B.
6. C 7. B

NaI / Acetone
8. (B)    2

(First SN )

9. (A) The nucleophilicity order is > > >

10. D 11. D 12. D 13. B 14. D
15. B 16. C 17. D 18. B 19. D

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1. CH MgBr ( excess )
1. (i) C6H5 – CH2CO2CH3  3  

 ?

2. H

1. Br , Heat , Light
(ii) C6H5C2H5  2    
 ? [JEE - 94]
2. NaCN

NaOH
2.  
 ? [JEE - 94]
S 2
N

3. Which statement is incorrect about the following reaction: [JEE - 1995]

(A) only one product is formed

(B) the product will have walden inversion
(C) the reaction mixture will have optical rotation zero
(D) the product is a mixture of D + L isomers
4. Optically active 2-iodobutane on treatment with NaI in acetone gives a product which does not
show optical activity. Explain briefly. [JEE - 95]

NaI
5.  C [JEE - 96]
Acetone

6. An alkyl halide (X) of formula C6H13Cl on treatment with potassium tertiary butoxide gives two
isomeric alkenes (Y) and (Z) of formula C 6H 12. Both alkenes on hydrogenation give
2,3-dimethylbutane. Predict (X), (Y) and (Z). [JEE - 96]
7. (i) A hydrocarbon A, of the formula C8H10, on ozonolysis gives compound B(C4H6O2) only. The
compound B can also be obtained from the alkyl bromide, C (C3H5Br) upon treatement with
magnesium in dry ether, followed by carbon dioxide and acidification. Identify A, B and C and also
give equations for the reactions.
(ii) A compound D(C8H10O) upon treatment with alkaline solution of iodine gives a yellow precipitate.
The filtrate on acidification gives a white solid E (C7H6O2). Write the structures of D, E and explain
the formation of E. [JEE - 1996]
8. Cl – CH2 – CH2 – CH2 – COPh + KOH + MeOH  ? [JEE - 97]

9. + KNH2   A [JEE - 97]

10. Which of the following is an organometallic compound

(A) Lithium methoxide (B) Lithium acetate
(C) Lithium dimethylamide (D) Methyl lithium [JEE-1997]

11. (CH3)3CMgCl on reaction with D2O produces : [JEE-1997]

(A) (CH3)3CD (B) (CH3)3OD (C) (CD3)CD (D) (CD3)3OD
12. Which of the following is the correct method for synthesizing methyl–t–butylether and why ?
(i) (CH3)3C Br + NaOMe  (ii) CH3Br + NaO–t–Bu  [JEE - 97]

13. Complete the following giving the structure of the principal organic products.

[JEE - 1997]

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14. The reaction with HBr gives : [JEE-1998]

(A) (B)

(C) (D)

15. Which of the following will react with water : [JEE-98]

(A) CHCl3 (B) Cl3CCHO (C) CCl4 (D) ClCH2CH2Cl
alcoholic KOH, heat
16. C6H5CH2CHClC6H5    [JEE - 98]

17. Benzyl chloride (C6H5CH2Cl) can be prepared from toluene by chlorination with :
(A) SO2Cl2 (B) SOCl2 (C) Cl2 / h (D) NaOCl
[JEE - 1998]
18. (b) Show the steps to carry out the following transformations.
(ii) Ethylbenzene  2-phenylpropionic acid [JEE - 1998]
CH3
|
C H OH
CH3  C  CH2Br 2 5 

19.  [JEE - 2000]
|
CH3
20. An SN2 reaction at an asymmetric carbon of a compound always gives
(A) an enantiomer of the substrate (B) a product with opposite optical rotation
(C) a mixture of diastereomers (D) a single stereoisomer [JEE-2001]
21. An alkene (A) C16H16 on ozonolysis gives only one product (B) C8H8O. Compound (B) reacts with
NaOH / I2 yields sodium benzoate. Compound (B) reacts with KOH / NH 2NH2 forming
(C) C8H10. Write the structures of compound (A), (B) & (C). [JEE - 2001]
22. Identify the set of reagent / reaction conditions ‘X’ and ‘Y’ in the following set of transformations
X Y
CH3 – CH2 – CH2Br  Product  CH3 CH  CH3 [JEE-2002]
|
Br
(A) X = dilute aqueous NaOH, 20°C
Y = HBr / Acetic acid, 20°C
(B) X = Concentrated alcoholic NaOH, 80°C
Y = HBr / acetic Acid, 20°C
(C) X = dilute aqueous NaOH, 20°C
Y = Br2 / CHCl3, 0°C
(D) X = Conc. alcoholic NaOH, 80°C
Y = Br2 / CHCl3, 0°C

23. Consider the following reaction : [JEE-2002]


CH3  CH  CH  CH3  Br  X  HBr
| |
D CH3
Identify the structure of the major product ‘X’ :-
 
(A) CH3  CH  CH  C H2 (B) CH3  CH  C CH3
| | | |
D CH3 D CH3
 
(C) CH3  C CH  CH3 (D) CH3  C H  CH  CH3
| | |
D CH3 CH3

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CH MgBr
24. Ethylester  3  
 P. The product P will be [JEE-2003]
excess

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

25. The order of reactivity of compound I - III towards phenyl magnesium bromide is
[JEE-(scr.)2004]
PhCOPh CH3 CHO CH3 COCH3

I II III
(A) I > II > III (B) II > I > III (C) II > III > I (D) III > II > I

26. The number of chiral compounds produced upon monochlorination of 2-methylbutane is

[JEE-(scr.)2004]
(A) 2 (B) 4 (C) 6 (D) 8

27. 1-Bromo-3-chlorocyclobutane will react with two moles of Na in ether producing [JEE-(scr.)2005]

(A) (B) (D) (D)

28. Phenyl magnesium bromide reacting with t-Butyl alcohol gives [JEE-(scr.)2005]

(A) Ph – OH (B) Ph – H (C) (D)

29. Compound (X) is reacted with aqueous acetone it gives

following products.

[JEE-(scr.)2005]

(A) K, L (B) K, M (C) 'L' only (D) 'M' only

30. Explain the following observations [JEE(M)-05]

Acidic solution

Neutral solution

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Answers
LEVEL - JEE

1. (i) (ii) 2. 3. D

5.

6. (X) (2-chloro -2, 3-dimethyl butane)

(Y) (2, 3, 4-trimethyl but-1-ene)

(Z) (2, 3-dimethyl but-2-ene)

7. (i) (A) (B) (C)

(ii) (D) (E)

8.

9. (A) Ph – C  C – Ph ( = Elimination)

10. D 11. A
12. equation (ii) is better method. In equation (1) Isobutene will be the major product due to
elimination.
13. It is Ullmann’s reaction
Heat

(  CuI2 )

14. B 15. B 16. +

17. (A, C)

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Br / h Mg / THF (i) CO
2
18. (ii) 2      
(ii) H2O / H

CH3
|
19. CH3  C  CH2  CH3 20. D
|
OC2H5

21. (A) or

O
||
(B) C 6H5  C  CH3 (C) C6H5 – CH2 – CH3

22. B 23. B 24. A 25. C 26. B

27. A 28. B 29. A

30. + HBr (strong acid)

(SN1 reaction)

No reaction

Because aryl halide have resonance stabilized C – X bond, and do not give SN reaction.

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