1

LAKSHAY (JEE)
Haloalkane & Haloarene DPP-01

1. Identify which of the compound having 2 4. Find the product p in following Rex
alcohol? OH

SOCl2
(A)
Cl Cl
(B) Cl

(A) (B)

(C) Cl

OH
Cl
(D)
(C) (D)
Cl
2. Luca’s Test conduct at fast rate by which
alcohol?
(A) CH3 ––CH2 ––CH2 ––OH 5. Best method to convert alcohol to halide is:
(A) ROH + SOCl2 → R – Cl + SO 2 + HCl
(B) CH3 CH CH3
OH (B) R − OH + PCl3 → R − Cl
CH3 (C) R − OH + PCl5 → R − Cl
(C) H3C C OH (D) R − OH + HCl → R − Cl + H 2O
CH3
(D) None 6. What is the major product of the following
reaction?
CH3
3. Find the product p in following CH3 ––CH2 |
heat
––CH2 ––OH + PX5 → …. CH3 − C — CH CH 3 + HBr ⎯⎯⎯
→
| OH
(A) CH3 ––CH2 ––CH2 ––X CH3
(B) H3C CH CH3 CH3 Br
| |
X (A) CH3 − C — CH CH3
X |
CH3
(C) H3C C CH3 CH3
X |
(B) CH 3 − C — CH 2 CH 2
CH2 CH2 CH2 | |
CH3 Br
(D)
X X
 2

CH3 (C) Alcohol and SOCl2 are soluble in water

| (D) The reaction does not occurs via
(C) CH3 − C — CHCH3 intermediate formation of an alkyl
| |
Br CH3 chloro sulphite
CH3
| 9. Which of the following reactions is not
(D) CH3 − C − C H 2CH3 possible?
|
CH 2Br (A) R – OH + NaBr → R – Br + NaOH
(B) R – OH + HBr → R – Br + H2O
(C) both reactions are possible
7. Alkyl halide can be prepared from: (D) both reactions are not possible
(A) Alkene (B) Alcohol
(C) Carboxylic acid (D) All of these

8. The reaction of SOCl2 on alkanols to form

alkyl chlorides gives good yields because:
(A) Alkyl chlorides are immiscible with
SOCl2
(B) The other products of the reaction are
gaseous and escape out
Answer Key
1. (B)
2. (C)
3. (A)
4. (A)
5. (A)
6. (C)
7. (D)
8. (B)
9. (A)

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 1

LAKSHAY (JEE)
Haloalkane & Haloarene DPP-02

4. Find the product P in following reaction-

1.

Which is correct statement about X and Y

(A) X is product of ionic reaction and Y is
(A)
product of radical reaction.
(B) X and Y both are product of ionic
reaction.
(C) X and Y both are product of radical
(B)
reaction.
(D) X is radical reaction and Y is ionic
reaction.
(C) Both the above
2. How many possible monochloro structural
(D)
isomers expected to be formed on free
radical monochlorination of (CH3)2CHCH2
CH3.
(A) 4 (B) 3
(C) 2 (D) 5 5. Write the structure of the major product in
the reaction-
acetone 𝑃𝑒𝑟𝑜𝑥𝑖𝑑𝑒
3. For the reaction R – Cl + NaI → R–I+ CH3 – CH2 – CH = CH2 + HBr →
NaCl which alkyl chloride will give
(A) CH3 − CH 2 − CH − CH3
maximum yield? |
CH3 Br
| (B) CH3 − CH 2 − CH 2 − CH 2
(A) CH3 − C − Cl |
| Br
CH3
(C) Both (A) and (B)
(B) CH3 – CH2 – CH2 – Cl
(D) CH3 − CH − CH 2 − CH3
(C) C6 H5 − CH − Cl |
| Br
CH3
CH3
|
(D) C6 H5 − C − Cl
|
CH3
 2

6. Find the product in following reaction- 7. CH3 – CH2 – CH = CH2 + HCl ⎯⎯ → Product
Identify the product in above reaction
(A) CH3 − CH 2 − CH 2 − CH 2
|
(A) Cl
(B) CH3 − CH 2 − CH − CH3
|
(B) Cl
(C) CH3 − CH − CH 2 − CH3
|
(C) Cl
(D) CH 2 − CH 2 − CH = CH 2
(D) None of these |
Cl

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Answer Key
1. (A)
2. (A)
3. (B)
4. (A)
5. (B)
6. (A)
7. (B)

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 1

LAKSHAY (JEE)
Haloalkane & Haloarene DPP-03

CH3
1. In the given Reaction |
CH3 (iii) CH3 – CH – CH  CH 2
C7 H12 (A) 

HBr
Br [Major (A) I > II > III (B) II > I > III
(C) III > II > I (D) III > I > II
Product]
CH2
4. What will be major product, when 2-methyl
CH=CH2 butane undergoes bromination in presence
(A) (B) of light ?
(A) 1-bromo – 2 – methyl butane
CH3 (B) 2-bromo – 2 – methyl butane
(C) (D) All of these (C) 2-bromo – 3 – methyl butane
(D) 1-bromo – 3 – methyl butane

5. Give the product obtained from the

Reaction?
2. NBS
CCl4 peroxide


NBS
hv
P
 
Na,ether
(x), x is 
Br
Br
(A) (B)
Br
(A)
(B)
Br

(C) (D) All of these

(C)
CH3

6. 
NBS
hv
 P, product P is : 

(D) All of these CH2–Br CH3

Br
3. Find out the correct order of Rate of reaction (A) (B)
towards allylic substitution :
(i) CH3 – CH = CH2
(ii) CH3 – CH2 – CH = CH2
 2

CH3 9. What arethe product of following reaction?

CH3
Ph – CH  Ch – CH 3  HBr 
[A]
(C) (D) (A) PhCH (Br) – CH2 – CH3
Br (B) Ph – CH2 – CH (Br) (CH3)
Br (C) Both (A) and (B)
(D) None
7. What is the major product of the following
Reaction?
CH3 10. Find the product P in following Reaction –
 
HBr
 [P] CH3
 HCl 
[P]
Br CH2Br
CH2CH3
(A) (B)
Cl
CH3 CH3
CH3 (A)
(C) (D) Br CH2CH3
Br H
CH3
(B)
8. Which is finkelstein Reaction? CH2CH3
(A) R – X  NaI  acetone Cl
(C) Both (A) and (B )
(B) R – X  AgF 
 (D) None

(C) R – X  NaF 

(D) R – X  AgCl 


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Answer Key
1. (D)
2. (C)
3. (C)
4. (B)
5. (A)
6. (A)
7. (D)
8. (A)
9. (A)
10. (A)

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 1

LAKSHAY (JEE)
Haloalkane & Haloarene DPP-04

5. Find the product p in following reaction –

CH3—CH—CH 3
1. What is the main product of the Reaction
between 2-methyl propene with HBr. U ⋅V Light
+ Cl2  → [P]
(A) 1 - bromobutane
(B) 1 – bromo -2- methyl propane CH3—CH—CH 2—Cl
(C) 2 – bromobutane
(D) 2 – bromo -2- methyl propane (A)
Cl
2. In the
given reaction : C6H5N2Cl CH3—C—CH 3
HF/BF3 /∆

→ [P]
(B)
Prduct [P] will be:
⊕ Ξ CH3—CH—CH 3
(A) C6 H 5 — N ≡ N BF4 Cl
(B) C6H5—F (C)
(C) C6H5—Cl
CH3—CH—CH 3
(D) C6H5—H

⊕ (D)
N ≡ N BF4
Cl

3. ∆
 → A, in the Reaction 6. In electrophilic substation Rex Toluene react
with Iodine we use oxidising agent (HNO3,
A is HIO3) due to
(A) fluorobenzene (A) reversible nature of reaction
(B) Benzene (B) irreversible nature of reaction
(C) 1, 4 difluorobenzene (C) redox reaction
(D) 1, 3 difluorobenzene (D) None of these
4. Diazonium Salt + Cu2Cl2 + HCl
Cl ⊕ 
7. In the sandmeyer reaction –  N ≡ N  x

→  
the reaction is known as - group of diazonium salt is replaced by
(A) halide group
(A) chlorination (B) nitro group
(B) Sandmeyer’s Reaction (C) –OH group
(C) (A) and (B) both (D) –NHNH2 group
(D) Substation Rex
 2

8. Which reagent is used to get iodobenzene N2 X N2 X

X X
from benzene diazonium acid sulphate
[C6H5N2HSO4] (C) (D)
(A) CUBr, ∆ X
(B) CU powder, +HI 10. Find the product p in following reaction –
(C) KI, ∆
(D) None of these Cl2
 → P
Fe/AlCl3

9. Aniline in set of reaction yielded end product Cl

B. (A) (B)
NH2 Cl
Cl

NaNO 2 +HCl
 → A 
Cu 2 x 2
→ B (C) (D)
[0–5°C Cl
X X
X
(A) (B)

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Answer Key
1. (D)
2. (B)
3. (A)
4. (B)
5. (B)
6. (A)
7. (A)
8. (C)
9. (A)
10. (A)

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 1

LAKSHAY (JEE)
Alkyl and Aryl halides DPP-05

1. Order of rate of reaction with AgNO3 or rate CH 3

of SN1: |
5. CH 3  C  Br CH 3  CH  Br
Cl Cl Cl | |
CH 3 CH 3
(a) (b)
CH 3  CH 2  CH 2 Br
(I) (II) (III) (c)
(A) I > III > II (B) II > III > I Reactivity toward SN1:
(C) I > II > III (D) III > I > II (A) a > b > c (B) b > a > c
(C) b > c > a (D) c > b > a
2. Which of the following is least reactive
towards SN1?
6. Assuming no other changes, what is the
I I
effect on rate of reaction if the
concentrations of both alkyl halide and the
nucleophile are doubled?
(A) (B)
CH3Br + HOΘ  CH3OH + BrΘ
I I (A) no change
(B) doubles the rate
(C) triples the rate
(C) (D) (D) quadruples the rate

3. SN1 reactivity of the following halides, 7. Assuming no other changes, what is the
(i) (CH3)3CBr (ii) (C6H5)2CHBr effect of doubling oly the concentration of
(iii) (C6H5)2C(CH3)Br (iv) (CH3)2 CHBr the alkyl halide in the following SN1
will be in the order: reaction?
(A) iv > i > ii > iii (B) ii > i > iii > iv (CH3)3CBr + IΘ  (CH3)3CI + BrΘ
(C) i > iii > ii > iv (D) iii > ii > i > iv (A) no change
(B) doubles the rate
4. The compound which would undergo SN2 (C) triples the rate
reaction fastest is: (D) quadruples the rate
Cl
8. Which of the following alkyl halides gives
(A)
the fastest SN1 reaction?
Cl (A) CH3CH2CH2Br (B) CH3CHCH3
(B) |
Br
(C) Br (C) CH3CHCH3 (D) CH3CH2CH2I
Br |
I
(D)

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 2

9. Which of the following alkyl halides gives 12. Compare rate of reaction with Ag  NO 3 or
the fastest SN1 reaction? rate of S N1 reaction:
Br Br
| Br Br
(A) CH 3CHCHCH 3
|
CH 3
(i) (ii) (iii)
(B) CH3CHCH 2 CH 2 Br
| (A) i > iii > ii (B) i > ii > iii
CH3 (C) iii > ii > i (D) ii > i > iii
Br
|
(C) CH 3CCH 2 CH 3 13. Compare rate of reaction with Ag  NO 3 or
| rate of SN1 reaction:
CH 3
I I I
(D) ClCH 2 CHCH 2 CH3
|
CH3
(i) (ii) (iii)
10. Which of the following factors has no effect
on the rate of SN1 reactions? (A) i > ii > iii (B) ii > iii > i
(A) the nature of the alkyl halide (C) ii > i > iii (D) i > iii > ii
(B) the nature of the leaving group
(C) the concentration of the alkyl halide
(D) the concentration of the ucleophile

11. Which of the following is the rate law for

SN1 mechanisms?
(A) Rate = k[Alkyl Halide][Nucleophile]
(B) Rate = k[Nucleophile]
(C) Rate = k[Alkyl Halide]
(D) Rate = k[Alkyl Halide][Nucleophile] +
k2[Alkyl Halide]

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Answer Key
1. (C)
2. (A)
3. (D)
4. (C)
5. (A)
6. (D)
7. (B)
8. (C)
9. (C)
10. (D)
11. (C)
12. (B)
13. (B)

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 1

LAKSHAY (JEE)
Alkyl and Aryl halides DPP-06

1. In the given reaction: 3. Which is the best leveling group in a

substitution reaction of an alkyl halide?
C2 H5
| (A) Cl– (B) Br–
CH3  C  Br 
NaI/HOH/Acetone
[P]
| (C) I– (D) F–
C3 H 7
Product (P) will be: 4. Order of nucleophilicity in polar protic
C2 H5 C2 H5 solvent?
| | (A) IΘ > BrΘ > ClΘ > FΘ
(A) CH3  C  I (B) I  C  CH 3
| | (B) FΘ > ClΘ > BrΘ > IΘ
C3 H 7 C3 H 7
(C) IΘ > ClΘ > BrΘ > FΘ
I
| (D) FΘ > IΘ > BrΘ > ClΘ
(C) CH 3  CH 2  CH 2  CH
 CH 2  CH 2  CH 3 5. Which statement is true with respect to an
(D) Mixture of (A) and (B) SN2 reactions?
(A) A good leaving group is a strong base
2. Which of the following combinations is (B) A good leaving group is a weak base
correctly matched? (C) A leaving group must be negatively
charged
H (D) A leaving group must be a halide
|
(A) CH3  C  Cl, S 2 , Walden inversion
N
| 6. What is the most reactive alkyl halide for the
D following reaction?
Br Br
H e
| e
(B) CH3  C  Cl, S 1 , Walden inversion (A) (B)
N
|
D Br Br
e e
C2 H5
| (C) (D)
(C) C6 H5  C  Cl, S 1 , Only retension
N
|
CH3 7. Given the major product of the following
C2 H5 reaction.
| Br
HO–
(D) C6 H5  C  Cl, S 1 , Only inversion Br
N
H3C 1 equivalent
| CH3
CH3

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 2

HO Br 9. Which of the following compound given

(A) same SN1 an SN2 product?
H3C CH3
OH (A)
(B) Br Cl
H3C CH3 Cl
H
(B)
(C) Br CH3
H3C CH3
H
(C)
Br Cl
(D)
CH3
CH3 (D)
Cl

CH3 10. Most reactive toward SN2:

H Br NaI/acetone (A) CH3 – Cl
8. H e
Cl (SN2) condition (B) H2C = CH – Cl
CH3 Cl
CH3 CH3
(C)
H I H I
(A) H Cl (B) Cl H (D) CH3 – F
CH3 CH3
CH3 11. Which of the following species is most
I H reactive in an SN2 reaction?
(C) H (D) (A) CH3CH2 – Cl (B) CH3CH2 – Br
Cl
(C) CH3CH2 – I (D) CH3CH2 – F
CH3

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 3

Answer Key
1. (D)
2. (A)
3. (C)
4. (A)
5. (B)
6. (C)
7. (B)
8. (C)
9. (C)
10. (A)
11. (C)

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 1

LAKSHAY (JEE)
Alkyl and Aryl halides DPP-07

1. Which one of the following compounds will

be most reactive for SN1 reactions?
(D)

(A) (B)
3. Which of the reactions shown below will be
faster?
Reaction-1:

(C) (D)

Reaction-2:
2. In the given reaction:

(A) Reaction 1 (B) Reaction 2

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

4. Product (A)

(B)
is:

(A) (B)
(C)

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 2

8. Which of the following nucleophilic

substitutions is practically not possible?
(C) (D)
(A)

S
+ OH − ⎯⎯→
2
5.
N
A; (B)

A is (C) Both (A) and (B) (D) None of these

(A) 9. CH3 − CH2 − Br + NaOH ⎯⎯

K3
→ CH3 −
CH 2 − OH + NaBr → reaction ......(1)
CH3
(B) |
CH 3 — C — CH 2 — Br + NaOH ⎯⎯
K3
→
(C) Both (A) and (B) |
CH3
(D)
(CH 3 )3 C — CH 2 — OH + NaBr ⎯⎯
→ reaction ......(2)
K1 and K2 are rate constant for above
reactions, correct relation is:
6. In the given reaction (A) K1 = K2 (B) K1 > K2
(C) K1 < K2 (D) K1 << K2

10. Which of the following nucleophiles is

going to promote an SN 2 reaction?

(A) NaI (B) Water

(A) (B)
(C) NH4Cl (D) MeONa
(C) Mixture of (A) and (B)
11. What is the major product of the following
synthesis?
(D)

7. Which of the following reactions is not (A)

possible?
(A) R — OH + NaBr → R – Br + NaoH (B)
(B) R — OH + HBr → R — Br + H2O
(C) both reactions are possible (C)
(D) both reactions are not possible
(D)

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Answer Key
1. (A)
2. (A)
3. (B)
4. (A)
5. (C)
6. (D)
7. (A)
8. (A)
9. (B)
10. (A)
11. (C)

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 1

LAKSHAY (JEE)
Alkyl and Aryl halides DPP-08

1. Which one of the following compound undergoes E1 reaction most readily?

CH 3
|
(A) CH 3  C  CH 2  CH 3 (B) CH 3  CH 2  CH 2  Br
|
Br
CH 3
|
(C) CH 3  CH 2  CH 2  I (D) CH 3  C  CH 2  CH 3
|
I

Br
2. In the given reaction, CH3OH . [X] as the major product among the elimination
C – CH3 
CH3
product is:
CH3
(A) (B) C – CH3
C = CH2
CH3
CH3
(C) CH3 (D)
CH3
CH3

3. In the given reaction following products are expected.

CH2 – Br CH3 CH2 – OCH3 OCH3
CH3OH
OCH3

+ + + + CH3
(I) (II) (III) (IV) (IV)
Which observations seem to be incorrect?
(A) Ist is the major product obtained by E1 reaction
(B) Vth is the major product obtained by SN1 reaction
(C) Formation of II or V involves a strained carbocation intermediate
(D) In the solvolysis reactions a carbocation intermediate is formed
 2

4. Which of the following reaction is not feasible?

CH3 CH3
CH3
CH3 CH3
(A) C – CH3 
CH3OH +
OCH3
Cl
CH3 CH3
C2H5OH
(B) Br OC2H5 +


CH3 CH3 CH3

C2H5OH
(C) + +

Br OC2H5 OC2H5
CH3 CH3
IΘ
(D) CH3 – C – Cl CH3 – C + HCl +
IΘ CH CH2
3

5. Which of the following cannot undergo E2 reaction?

(A) Br (B)
Br

(C) (D)
Br Br
6. Arrange the following in decreasing order of stability of their transition state during elimination by
strong base
Br

Br Br
(I) (II) (III)
(A) II > I > III (B) II > III > I
(C) I > III > II (D) I > II > III
7. 2-Chlorobutane on treatment with alcoholic KOH/ gives mainly:
(A) 2-Butene (B) 1-Butene
(C) 2-Butanol (D) 1-Butyne

8. Select the formula representing the major product of the following reaction
Br H
CH3CH2OK/CH3CH2OH
H CC CH3 
CH3 CH2CH3
H H
H CH3 CC CH3
(A) (B)
H2C
CH3 CH2CH3 CH2CH3
Br H
H CH2CH3 H5C2O CC CH3
(C) (D)
CH3 CH3 CH3 CH2CH3
 3

Cl
|
t  BuO
9. CH3  CH  CH  CH3  
 Major product is:
|
CH3
(A) CH3  C  CH  CH3 (B) CH3  CH  CH  CH 2
| |
CH3 CH3
OH
|
(C) CH 2  C  CH 2  CH3 (D) CH 3  CH  CH  CH 3
| |
CH3 CH 3

10. Which of the following will undergo fastest elimination reaction with alcoholic KOH?
Br Br
(A) (Cis) (B) (trans)
Me Me
Br Me Br
(C) (D)
Me

MeO ‘K’
X Major

11. CH3 – CH – C(Br)CH3

CH3 CH3 Y Major
Et3CO ‘K’
X and Y are respectively:
CH3 CH3 (CH3)2CH H
(A) C=C and C=C
CH3 CH3 CH3 H
(CH3)2CH H CH3 CH3
(B) C = C and C=C
CH3 H CH3 CH3
CH3 CH 3
(C) Both C=C
CH3 CH3
H C(CH3)3
(D) Both C=C
H CH3
 4

Answer Key
1. (D)
2. (C)
3. (B)
4. (D)
5. (C)
6. (A)
7. (A)
8. (C)
9. (B)
10. (A)
11. (A)

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 1

LAKSHAY (JEE)
Alkyl and Aryl halides DPP-09

1. Which of the following reaction is SN2Ar reaction?

CH3 CH3
Br NO2
   
(A) +Br +H (B) +NO2 +H

Cl OH
Θ Θ
+ OH  + Cl
Θ Θ
(C) (D) Br + OH OH + Br
NO2 NO2

2. Which of the following compound gives fastest SN2 Ar reaction?

Cl Cl
NO2
(A) (B)

NO2
Cl Cl
NO2 NO2
(C) (D)

NO2 NO2

3. Which of the following compound gives fastest SN2 Ar reaction?

Br Cl
NO2
(A) (B)

NO2 NO2
Br Cl
NO2
(C) (D)

NO2 NO2
 2

CN

(CH3)2NH
4. Cu2O, 
The product is

F
NMe2 CN

(A) (B)

NMe2 NMe2
CN NMe2

(C) (D)
NMe2
F F

5. Which of the following species is expected to have maximum enthalpy in an electrophilic aromatic
substitution reaction?
H E+ H E H+ E E
+ +
+ E+ +
EEE
(I) (II) (III) (IV) (V)
(A) Species (II) (B) Species (III)
(C) Species ((IV) (D) Species (V)

6. The reagent used for Friedel-Craft’s reaction is:

(A) Dry ether (B) AlCl3
(C) Anhydrous AlCl3 (D) P2O5

7. The compound with molecular formula C8H10 which give two isomers on electrophilic substitution
with Cl2/FeCl3 or with HNO3/H2SO4 is:
(A) p-Dimethyl benzene (B) m-Dimethyl benzene
(C) o-Dimethyl benzene (D) Ethyl benzene

8. Which of the following will undergo sulphonation at fastest rate?

(A) (B)

(C) (D)
 3

9. Which among the following is deactivating group?

(A) –Cl (B) –OR
(C) –NH2 (d) –NHR

10. The compound X in the reaction is:

Anhydrous AlCl3
+ ICl X:

Cl I
(A) (B)

Cl I

(C) (D)
Cl
I
 4

Answer Key
1. (C)
2. (C)
3. (B)
4. (B)
5. (A)
6. (C)
7. (C)
8. (B)
9. (A)
10. (B)

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 1

LAKSHAY (JEE)
Alkyl and Aryl halides DPP-10

1. The relative reactivity of acyl compounds towards nucleophilic substitution are in the order of
(A) Acid anhydride > Amide > Ester > Acyl chloride
(B) Acyl chloride > Ester > Acid anhydride > Amine
(C) Acyl chloride > Acid anhydride > Ester > Amide
(D) Ester > Acyl chloride > Amide > Acid anhydride

CH3
C–OCH3
PhMgBr
2. (P). Product (P) is:
O (1 equivalent)
CH2–COCH3
O
CH3 O CH3 O
C–Ph C–Ph
(A) (B)
CH2–COCH3 CH2–COCH3
O O
CH3 CH3
C–Ph C–OCH3
(C) (D)
O O
CH2–COCH3 CH2–C–Ph
CH3
O O

3. In which of the following reaction 2° alcohol is obtained as a product?

(1) CH3MgBr (1) MgCl

(A) (2) H2O (B) CH3 O (2) H2O
O
O
(C) (1) CH3MgBr (D) Both (A) and (B)
(2) H2O

4. End product of the given reaction is:

Cl
Mg 1. CH2O
(A) (B)
Et2O 2. H2O
 2

OH
OH
(A) (B)

OH
(C) (D)

5. Consider the following compounds:

(i) COCl (ii) O2N COCl

(iii) H3C COCl (iv) OHC COCl

The correct order of reactivity towards hydrolysis is:

(A) (i) > (ii) > (iii) > (iv) (B) (iv) > (ii) > (i) > (iii)
(C) (ii) > (iv) > (i) > (iii) (D) (ii) > (iv) > (iii) > (i)

O CH3
(1) PhMgBr
6. C Products; product obtained in this reaction are:
(2) H+
||
O
(A) disastereomers (B) racemic
(C) pure enantiomer (D) meso

O
CH3NH2
7. C–OCH3 Heat
X,X is:

O
(A) NH–C–CH3 (B) NH–CH2–CHO

O O
(C) C–NH–CH3 (D) C–CH3–NH2

8. Which of the following will undergo acid-base reaction with Gingnard reagent?
(A) HC  CH (B) R – OH
(C) R – CO2H (d) All of these
 3

Answer Key
1. (C)
2. (D)
3. (D)
4. (B)
5. (C)
6. (B)
7. (C)
8. (D)

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 1

LAKSHAY (JEE)
Alkyl and Aryl halides DPP-11

RMgBr
1. Product; The product
S
O O
(A) HSO2 – CH2 – CH2 – CH2 – CH2 – R (B) H – SO2(CH2)3 – R

(C) (D) H – SO2(CH)3 – R

MgBr
SO2

2.
(i) THF
+ MgBrCH2CH2CH2CH2MgBr (ii) H3O+
O O
product; Product of the reaction is:
O
||
(A) HO – (CH2)3 – C – CH2 – CH2 – CH3 (B)

HO (CH2)3—OH

(C) (D)
HO CH – CH2 – CH3
|
OH HO CH2 – CH2 – CH3

3. Which of the following compound is not a suitable solvent for Grignard reaction?
O

O
(A) (B) (1, 4-dioxane)

O
(THF)

(C) CH3 – O – CH2 – CH2 – O – CH3 (D)

 2

MeO OMe
n-Bu2CuLi
4. Product of the reaction will be:
(n-Bu=n-butyl group)

Br
MeO OMe MeO OMe
(A) (B)

n-Bu n-Bu
OMe Bu OH OH
(C) (D)

Br Br

5. In the given reaction:

CH3MgBr
Product
H/H2O
O
Find the product of reaction.

(A) OH (B)

OH

(C) OH (D)

r1
6. (i) + PhMgBr
O
PhCH2CH2OH
r2
(ii) + PhMgBr
O
PhCH2CH2CH2 OH
(A) r2 > r1 (B) r1 > r2
(C) r1 = r2 (D) r1 = 2r2

7. Reaction – 1:
SH O SH OH
|| | CH3
HO C-Cl C
1. xCH3MgBr CH3
2. H3O CH3
OH C
C-Cl
|| | CH3
O OH
 3

Reaction – 2:
O OH
|| ||
C–O–Et CH3–C– CH3

1. yCH3MgBr
2. H3O

CH2–Cl
CH2Cl
What is the ratio of (x/y) in above problem?
(A) 1.5 (B) 2
(C) 2.5 (D) 3
8. What product would you expect to obtain from Grignard reaction when an excess of phenylmagnesium
bromide reacts with dimethyl carbonate CH3OCOOCH3?
OH
| OH
(A) CH3 — C — Ph (B) |
| CH3 — CH — Ph
Ph
OH
| O
(C) Ph — C — Ph (D) ||
| CH3 — C — Ph
Ph

9. In which of the following reactions product formed is same?

O

MeMgX
(i) P

MgX
(ii) P

MgBr P
(iii) +

(A) (i) and (ii) (B) (ii) and (iii)

(C) (i) and (iii) (D) (i), (ii) and (iii)

10. Which of the following reaction sequences would be the best for synthesis of 2-pentanone?
OH
(A) ||
H3O
CH 3 — CH 2 — CH 2 — C — H ⎯⎯⎯⎯ CH3 MgI
Et 2 O
→ ⎯⎯⎯ →
 4

CH 2 — CH 2
(B) | |
H 3 O
CH3 — CH — O ⎯⎯⎯⎯
CH3 MgI
Et 2 O
→ ⎯⎯⎯ →

(C) CH3 — CH2 — CH2 — C  H 2 ⎯⎯⎯
CH3 MgI
Et 2 O
⎯
→ ⎯⎯⎯
H3 O
→
OH
||
(D) H3 O
CH3 — CH 2 — C — H ⎯⎯⎯⎯
CH3 MgI
Et 2 O
→ ⎯⎯⎯ →
(propanal)
 5

Answer Key
1. (C)
2. (B)
3. (D)
4. (A)
5. (C)
6. (B)
7. (B)
8. (C)
9. (D)
10. (C)

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