ORGANIC CHEMISTRY

Master Practice Problems

ALKYL HALIDE

JEE-ADVANCED MPP-1

SINGLE CORRECT TYPE

1. Best method to prepare O – CH3 is

the combination of

KOH CH3I OH 
Na CH3I
(A) OH      (B)    

Na
Cl
(C) MeOH 
 (D) (A) & (B) both

2. NaH Me– I
H OH   (X)   (Y)


Identify (Y)

H OMe H OMe
(A) (B) MeO H (C) (D) None of these

CH3
H OK EtBr
3.  Product
H CH3
Et

Correct stereochemical relationship between reactant and product will be

(A) Enantiomer (B) Diastereomer
(C) Structural isomer (D) None of these

4.  
RO Na + R – L ROR  + Na L

Rate of reaction will maximum when L is

(A) CF3SO3– (TRIFLATE ION) (B) CH 3 SO2 (p-Toluene sulphonate)

(C) Br– (D) I–

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5. Correct order of leaving group.

CH2 CH2

(A) > (B) I <N N

NO2
O O
(C) CH3 – C – O < CH3 – S – O (D) All
O

H F
6. + NaI (one mole)   Product will be
acetone
Br H

I F H F
(A) (B)
H H I H

H H H I
(C) (D)
Br I Br H

CH3
C – Br EtOH
(A)
7. 
CH3 (Strong-heated)

Major-product (A) is a type of mechanism is

OEt
(A) SN1 (B) (E1) (C) (E2) (D)
(E2)

CH3
Et Br
NaI
8. D H
acetone
H Br
CH3
Major product of the reaction is
CH3 CH3
Et Br Et Br
(A) D H (B) D H
H I I H
CH3 CH3

CH3
I Et
(C) CH3 – CH = CD – CH – CH3 (D) D H
H Br
Br
CH3

2
 Me

SOCl2
9. H OH    ‘P’

D
Product ‘P’ is
(A) Inverted Product (B) Racemic (C) Retention Product (D) Meso

10. Hydrolysis of methyl bromide takes place much faster in the presence of
(A) KF (B) KI (C) KBr (D) KCl

11. Treatment of (S)-2-bromobutane with sodium hydroxide results in the production of a compound with an (R)
configuration. The reaction has most likely taken place through :
(A) an SN1 mechanism (B) an SN2 mechanism
(C) both SN1 and SN2 reaction (D) cannot be determined

12. Which of the reactions shown below will be faster ?

KOH KOH
Reaction 1:  ; Reaction 2: 
H2O Crown ether

(A) Reaction 1 (B) Reaction 2

(C) Both have equal rates of reaction (D) Cannot be predicted

KSH
13.  

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

14. Give the structure of the reactant that could be used to convert iodoethane into given compounds ?

S – CH2–CH3

CH3

   
SK SK
(A) (B)
CH3 CH3

   
SK SK
(C) (D)
CH3 CH3

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15. Transition state of given SN2 is

CH2 – Br CH2 – O – R
R  O
  
SN2 reaction

+
+
 +
OR  (+) +
OR
H
H
(A) H (B)
H
Br
 Br
 (+)
+
+
 +
OR  (–) +
OR
H
H
(C) H (D)
H
Br
 Br
 (–)

CH3
H Br NaCN
16.    

H3C H DMSO, 25  C
CH2CH3

What is the major product of the reaction shown ?

CH3 CH3 CH3 CH3
H CN NC H H CN NC H
(A) H3C H (B) H3C H (C) H CH3 (D) H CH3
CH2CH3 CH2CH3 CH2CH3 CH2CH3
17. What are reactant X and product Y in the following sequence of reactions?

O O
H3C SCl H3C O–S CH3
O
NaN3
Reactant X H H O Product Y
pyridine Ethanol-water

Reactant X Product Y

H3C OH H3C N3 H3C OH H3C H

(A) H H (B) H N3
H H H H

H3C H H3C H H3C H H3C N3

(C) (D)
H OH H N3 H OH H H

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18. Trimethyloxonium tetrafluoroborate reacts with methanol (CH3OH) to give dimethyl ether (CH3OCH3). Which
equation, including the curved arrows, best represents the rate-determining step in the mechanism?

CH3
+ –
H3C–O: BF4
CH3
Trimethyloxonium tetrafluoroborate

CH3 CH3
+ +
H3C – O: H3C + :O:
(A)
CH3 CH3

CH3
.. +
(B) H3C – O: + H3C
+
H3C–O:
H H

CH3 CH3 CH3

.. + +
(C) H3C – O: + H3C – O: H3C–O: + :O:
H CH3 H CH3

CH3 CH3 CH3

..– +
(D) H3C – O : + H3C – O: H3C–O:
.. + :O:
H CH3 CH3

19. Which of the following conditions are best for an SN1 reaction and not an SN2 ?
(A) strong nucleophile, high solvent polarity.
(B) weak nucleophile, high solvent polarity
(C) strong nucleophile, low solvent polarity
(D) weak nucleophile, low solvent polarity

20. Which of the following ether can not react with HI ?

O
O O
(A) Ph – OCH3 (B) (C) (D)
Ph Ph

OH

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 ANSWER KEY

1. (B) 2. (A) 3. (D) 4. (A) 5. (D)

6. (A) 7. (B) 8. (B) 9. (C) 10. (B)
11. (B) 12. (B) 13. (D) 14. (C) 15. (D)
16. (B) 17. (B) 18. (C) 19. (B) 20. (D)