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 EXERCISE # I (MAINS ORIENTED)
1. Major product of following reaction is :
Cl
Cl
CH3OH
[X]
O Cl
(Excess)
Cl OCH3 Cl OCH3
Cl Cl OCH3 Cl
(A) (B) (C) (D)
O OCH3 O OCH3 O Cl O Cl

2. Which compound undergoes hydrolysis by the SN1 mechanism at the fastest rate?
CH3 CH3 Br CH3 Br CH3

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

3. Arrange the following compounds in decreasing order of their reactivity for hydrolysis reaction
CH3 Br
(I) C6H5–CH2–Br (II) C6H5 – CH – C2H5 (III) (IV) CH
Br
Br
(A) I > II > III > IV (B) IV > II > I > III (C) III > IV > II > I (D) IV > III > II > I

4. Which of the following is most reactive toward SN1 reaction?

CH2–Cl CH2–Cl CH2–Cl CH2–Cl

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

H CH3 OCH3 NO2

5. Arrange the following compounds in order of decreasing rate of hydrolysis for SN1 reaction:

(I) CH2 – Br (II) H3C CH2 – Br

CH3
(III) CH3 – CH2 CH2 – Br (IV) CH CH2 – Br
CH3
(A) II > III > IV > I (B) IV > III > II > I
(C) III > IV > II > I (D) I > II > III > I

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 1
6. Which one of the following compounds will give enantiomeric pair on treatment with HOH?
C2H5 CH3 H C2H5
(A) C6H5 C I (B) CH3 C Br (C) C6H5 C Br (D) C2H5 C Br
C2H5 C2H5 D CH3

7. Consider the SN1 solvolysis of the following halides in aqueous formic acid, decide decreasing
order of reactivity of above alkyl halide ?
Br Br CH3
CH3
(I) CH – CH – CH3 (II)
CH3
Br

(III) C6H5 – CH – C6H5 (IV)

Br
(A) III > IV > II > I (B) II > IV > I > III (C) I > II > III > IV (D) III > I > II > IV
8. For the given reaction, which substrate will give maximum racemisation?
R1 R1
X   R
HOH
R C C OH
R2 R2
CH3 CH3
(A) C6H5 C Br (B) CH2 =CH C Br
C2H5 C2H5
Br Br
(C) C6H5 C OCH3 (D) C6H5 C NO2

CH3 NH3

9. Major product of following reaction is :

D D
OH
?
H H
D I
D D
I I D
(A) (B) (C) (D) None of these
D D
C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 2

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10. If 96% racemisation takes place in given reaction then find out the correct statement :
CH3
H I 
HOH

Et
(A) Among the products 48% S and 48% R configuration containing molecules are present
(B) Among the products 50% S and 50% R configuration containing molecules are present
(C) Among the products 48% S and 52% R configuration containing molecules are present
(D) Among the products 52% S and 48% R configuration containing molecules are present

11. In the given reaction the product [P] can be :

CH3–CH=CH–CH2–OH 
HBr

SN 1'
 [P]
Br
|
(A) CH3–CH=CH–CH2–Br (B) CH 3  CH  CH  CH 2
Br
|
(C) CH2=CH–CH=CH2 (D) CH 3  CH  CH 2  CH 2  OH

12. Which of the following can not give SN1 reaction easily?
Br
Br Br Br

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

13. Which one of the following compounds will be most reactive for SN1 reactions ?
I Cl Br Cl
O O O
(A) (B) (C) (D)
O
14. Which of the following compounds is most rapidly hydrolysed by SN1 mechanism ?
(A) C6H5Cl (B) Cl–CH2–CH=CH2
(C) (C6H5)3CCl (D) C6H5CH2Cl

15. Among the bromides I–III given below, the order of reactivity in SN1 reaction is:
O

(I) (II) (III)

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

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 3

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16. Which of the following is most reactive toward SN2.
CH2 – Cl CH2 – Cl CH2 – Cl CH2 – Cl

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

H CH3 OCH3 NO2

17. For given reaction, the rate of reaction is given by the expression :
– –
CH3Br + OH  CH3OH + Br
–
(A) Rate = k [CH3Br] (B) Rate = k [OH ]
– –
(C) Rate = k [CH3Br][OH ] (D) Rate = k [CH3Br]º [OH ]º

18. Select suitable reason for non-occurence of the following reaction.

– –
Br + CH3OH  BrCH3 + OH
(A) Attacking nucleophile is stronger one
(B) Leaving group is a stronger base than nucleophile
(C) Alcohols are not good substrate for SN reaction
(D) Hydroxide ions are weak bases

19. Major product of following reaction is :

Br CH3 –
+ OH   
SN 2
H H
HO CH3 H CH3
(A) H (B) H
H OH
(C) Both (D) None of these

20. The reactivity of given compounds towards SN2 displacement is :

2-bromo-2-methylbutane 1-bromopentane 2-bromopentane
(I) (II) (III)
(A) I > II > III (B) I > III > II (C) II > III > I (D) II > I > III

21. For the given reaction ,CORRECT option regarding mechanism involved is :
Me Me Me Me
OH– OH–
HO H II
H Cl I
H OH + HO H
Et Et Et Et
(A) I can't be SN1 (B) II can't be SN2
(C) I can be SN1 & II can be SN2 (D) I can be SN2 & II can be SN1

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 4

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 –
22. In which of the following replacement of Cl is most difficult?

Cl Cl
(A) Cl (B) (C) (D)
Cl
23. Arrange these compounds in order of increasing SN2 reaction rate :
O

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

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

24. Which reaction proceeds faster with NaI in DMSO ?

CH2Cl
Cl
(A) CH3 (B)

Cl CH2Cl

(C) (D)

25. The major product in the given reaction is :

CH2Br
+ NH3 
Br
CH2NH2 CH2NH2
(A) (B)
Br NH2
CH2Br
(C) (D) All of these
NH2

26. The compound CH3–O–CH2–Br gives faster rate of nucleophilic substitution reaction than :
(A) CH3Br (B) CH3CH2Br (C) PhCH2Br (D) CH3OCH2Cl

27. Which will give white ppt. with AgNO3?

(A) Cl (B) Cl (C) CH2Cl (D) Both (A) and (C)

28. When ethyl bromide is treated with moist Ag2O, the main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 5

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29. When ethyl bromide is treated with dry Ag2O, the main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these
30. Major product of following reaction is :
CH3
OH 
SOCl2
H Pyridine

D
CH3 CH3
H
(A) H Cl (B) Cl H (C) H2C = CH2 (D) H2C = C
D
D D
31. Which reaction conditions (reagents) is suitable for the following reaction:

H–C–OH ? Br–C–H
| |
D D
(A)Br2 / CCl4 (B) SOBr2 (C) PBr3 (D) HBr / conc H2SO4

32. Major product of following reaction is :


(i) SH (1 eq.)
CH3–CH–CH2–CH2–CH–CH3 
 (ii) KOH

OTs OTs
(A) CH3–CH–CH2–CH2–CH–CH3 (B) CH3–CH–CH2–CH2–CH–CH3
OTs SK SK SK
CH3 CH3
S
CH3 CH3
(C) (D) S

33. Assuming all the substrate convert into substitution products containing 0.05 mole of S-
configuration, calculate the percentage of SN2 mechanism.
CH3
H OH 
TsCl
(A) 
KSH

Et
(1 mole)
(A) 90% (B) 80% (C) 70% (D) 95%
34. 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
(C) Alcohol and SOCl2 are soluble in water
(D) The reaction does not occurs via intermediate formation of an alkyl chloro sulphite

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 6

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35. Major product of following reaction is :
CH3
OH  
SOCl2
H Et 2O

D
CH3 CH3
H
(A) H Cl (B) Cl H (C) H2C = CH2 (D) H2C = C
D
D D
36. In the given pairs, which pair represent correct order of rate dehydrohalogenation reaction.
(A) Cl < (B) Cl <
Cl Cl
(C) (D) CH3 – CH2 – Cl < CD3 – CD2 – Cl
<
I Br

37. Major product of following reaction is :

O– CH2CH2 Br 
KOH
200C
 P;

(A) OH (B) O–CH2–CH2OH

(C) (D) O–CH = CH2

38. Major product of following reaction is :

CH3
H D C 2 H5 O –
H Br 
C2 H5OH

CH3
H3 C H H3C CH3
(A) C C (B) CC
H CH3 H H
H3C CH3 H3 C H
(C) CC (D) C C
H D D CH3

39. CORRECT order of rate of reaction for following compounds with Conc. HBr is :
CH3OH CH3CH2OH (CH3)2CHOH (CH3)3COH
(P) (Q) (R) (S)
(A) S>R>Q>P (B) P>Q>R>S (C) S>R>P>Q (D) P>S>Q>R

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 7

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40. If P & Q are the major products then P & Q are respectively :
HBr
P
(i) CH3I
Q
N (ii) HBr

Br Br
(A) I– (B)
& & I–
N N N Br N Br

Br Br
(C) & I– (D) & I–
N Br N N N Br

41. On heating glycerol with excess amount to HI, the product formed is
(A) Allyl iodide (B) Isopropyl iodide
(C) Propylene (D)1,2,3–tri-iodopropane

42. Major product of following reaction is :

Br
CH3 CCNa

Et 2O/ 


CC–CH3
(A) &
20% 80%
CC–CH3
(B) &
20% 80%
CC–CH3
(C)
100%

(D)
100%

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 8

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 EXERCISE # II-A
1. Rate of SN2 depends on :
(A) Conc of Nucleophile (B) Conc of substrate
(C) Nature of leaving group (D) Nature of solvent

2. In the given pair in which pair the first compound is more reactive than second towards S N2
reaction.
Cl
(A) Cl CH2Cl (B)
Cl
Cl Cl

(C) Cl Cl (D)

3. Which of following statements is(are) correct for the given reaction.

CH3
OTs  
NaCN
H (DMF)

C2H5
(A) Product formation takes place due to the breaking of C–O bond
(B) Hydrolysis of major product gives optically active carboxylic acid
(C) Reaction involves bimolecular nucleophilic substitution reaction
(D) Absolute configuration of major product is ―R‖
4. Which of the following statements is / are true?
(A) CH3–CH2–CH2–I will react more readily than (CH3)2 CHI for SN2 reactions.
(B) CH3–CH2–CH2–Cl will react more readily than CH3–CH2–CH2–Br for SN2 reaction.
(C) CH3–CH2–CH2–CH2–Br will react more readily than (CH3)3C–CH2–Br for SN2 reactions
(D) CH3–O–C6H4– CH2Br will react more readily than NO2–C6H5–CH2Br for SN2 reaction

5. Incorrect statement about alkyl halides is / are:

(A) Tertiary alkyl halides undergo SN2 substitutions
(B) Alkyl iodides on exposure to sunlight gradually darken
(C) Photo iodination is irreversible in presence of HIO3
(D) A nucleophilic substitution is most difficult in alkyl iodides

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 9

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6. Which of following reaction(s) produce Saytzeff product as a major product :
Cl


(A) 
NH 2

 (B) 
alc.KOH/

F

   OR
(C) 
Me3CO K

(D)
NMe3 
 
OR

Cl

7. SN1 & SN2 is not favourable in

(A) H2C = CH–Cl (B) Ph–CH2–Cl (C) Ph–Cl (D) H2C=CH–CH2–Cl

8. Among the following, which statement is correct ?

(A) Alkyl-aryl product can be obtained in wurtz reaction.
(B) Dipole moment of cyclohexyl chloride is more than that of chlorobenzene.
(C) Alchohols are insoluble in lucas reagent while their halides are soluble.
(D) Preparation of ether by acid dehydration of secondary alcohol is not suitable.

9. In which of the following reaction(s), configuration about chiral carbon is retained in the major
product
Me Me
OH    OH    
Na CH3Br SOCl2 CH3ONa
(A) H (B) H

D D

Me Me
H /MeOH
OH     OH 

PCl3 CH3ONa
(C) H (D) H

D Et

10. A gem dichloride is formed in the reaction :

(A) CH3CHO and PCl5 (B) CH3COCH3 and PCl5
(C) CH2 = CH2 and Cl2 (D) CH2 = CHCl and HCl

11. Assuming that all products are major & R is hydrocarbon while T is also organic product then
choose the correct option(s) ?
(i) Br2/h (i) Na (i) CH3-I
P Q R+S+T
(ii) H2O (ii) CS2 (ii)
(A) T is more acidic than P
(B) R has more heat of combustion than propene
(C) Both P & Q can show stereoisomerism
(D) S is not an organic product

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12. Which of following are correct for given reaction


OH–  
N

(A) Major product of reaction is

N

(B) Major product is

N

(C) Major product formation involve substitution

(D) The reaction is E2 reaction

13. Which of the following reactions is (are) incorrectly matched with their major product :
(A) Me3C–O–CH3 
HI
 Me3C–OH + CH3I
(B) H3C–O–CH2–CH3 
HI
 CH3OH + ICH2CH3

(C) O–CH3 
HI
 I + CH3OH
18
 18
(D) CH3–O–CH2CH3 
H3 O
 CH3OH + CH3CH2 O H

14. Correct statement among the following is/are :

(A) The rate of hydrolysis of tertiary butyl bromide increases by addition of Ag2O
–
(B) Aqueous Ag2O produces nucleophilic OH
(C) The addition of a small amount of oxygen slows down the photochemical chlorination of
methane.
(D) CH3CH2Cl is more reactive than PhCH2Cl for bimolecular nucleophilic substitution reaction

15. Incorrect statement among the following is/are:

(A) ROH with NaI in the presence of phosphoric acid gives RI, but not in the presence of H2SO4
(B) 2-methyl propane on chlorination (Cl2, hv) gives 1-chloro-2-methyl propane while
bromination (Br2, hv) gives 2-bromo-2-methyl propane
(C) Usually higher temperature prefers substitution over elimination
(D) Triphenyl chloromethane cannot be hydrolysed

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 11

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16. From left to right, correct statements are :
CH3 CH3 CH3
CH3 – C – Cl CH3 – C – Br CH3 – C – I
H H H
(A) Rate of SN1 mechanism increases in polar protic solvent
(B) Rate of SN2 mechanism increases in DMSO
(C) Rate of E2 mechanism increases
(D) Rate of E1 mechanism increases

17. How many monobromo derivatives are possible for Hydrocarbon (R) ?
O
aq.NaOH SOBr2 Na
CH2–O–S CH3 P Q R
Pyridine Et2O
O
(A) 2 (B) 3 (C) 5 (D) 1

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 12

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 EXERCISE # II-B
COMPREHENSION TYPE
Paragraph for Q.No. 01 to 02

Groups like CN & [–O– N = O]: possess two nucleophilic centre and are called ambident
nucleophiles. Actually cyanide group is hybride of two contributing structures and therefore can
act as nucleophile in two different ways . Similarly nitrite ion also
represents an ambident nucleophile with two different points of linkage [O – = O].
1. Correct option among the following :
(A) R  X  KCN
 RNC (B) R  X  AgCN
 R  CN
Haloalkane Major Pr oduct Major

(C) R  X 
KNO2
R  O  N  O (D) R  X 
AgNO2
R  O  N  O
Major Major product

2. Incorrect statement
KCN
R–X AgCN
(A) KCN is predominentely ionic in nature (B) AgCN is mainly covalent in nature
(C) In AgCN, carbon is the donor atom (D) In AgCN nitrogen is the donor atom

3. Match the List I with List II

List-I List-II
(A) CF3–CHCl2  CF2 = CCl2
alc. KOH/
(P) Elimination Reaction
CH3
(B) CH3 – C – OH H CH3 – C = CH2 (Q) Carbocation
CH3 CH3
(C) CH3–CH2–Br 
alc. KOH

 CH2 = CH2 (R) Carbanion
Br
EtOH
(D) CH3 – C – CH3  CH3 – C = CH2 (S) Free radical
CH3 CH3

4. Match List I with List II

List-I List-II
(Reactions) (Products)

(A) CH3–O–SO2CH3 + C2H5 O (P) CH3 – CH2 – PH2
(B) CH3–CH2–I + PH3 (Q) CH3 – O – C2H5
(C) HC  CNa + CH3 –CH2 – Br (R) CH3 – O – CH3

(D) CH3–Cl + CH3– O (S) CHC – CH2 – CH3

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5. Match List-I with List-II

Z – CH2Br + CH 3 O  Z –CH2 –OCH3 + Br 
List-I (Z–) List-II (Relative reactivity)
(A) H– (P) 0.1
(B) CH3– (Q) 3
(C) C2H5– (R) 1
CH3
(D) CH– (S) 100
CH3

6. Match the List I with List II

List-I List-II
CH3
(A) E1CB (P) CH3CH2CH2N–O
CH3
(B) Saytzeff alkene as major product (Q) CH3CH2CH2 – O – C – S – CH3
S
Cl
(C) E2 (R) CH3– CH2 – CH – CH3
(D) Ei (S) C6H5 – CH2 – CH – CH3
F

7. Column-I Column-II
(Reactions) (Characteristics)
(A) CH3CH2CH = CH2  
HBr
 (P) Bimolecular
(B) CH3CH2CH = CH2 
 HBr, Peroxide
(Q) Carbocation intermediate
PhCH(CH3)OH   SOCl
(C) 2
(R) Regioselective
(D) PhCH(CH3)OH 
 HBr
(S) Racemic modification
(T) Stereospecific reaction
8. Column-I Column-II

(Statements) (Consistent path of reaction)

(A) Reactions are concerted (P) SN1

(B) CH3X cannot react (Q) SN2

(C) 3º R–X > 2º R–X > 1º R–X (R) E1

(D) R–I reacts faster than R–Cl (S) E2

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 HBr, peroxide HBr Zn, Heat
9. C A B D (C6H12)
(Resolvable) (C6H11Br) (Non-resolvable) Symmetrical
Decolourise Br2water Alkene
and cannot be resolved
Alc. KOH

E
a single possible pruduct
Identify A, C & E in the sequence of reaction.

10. CH3–CH2I reacts more rapidly with strong base in comparison to CD3CH2I.

11. Predict the product(s) and write the mechanism of the given reaction :
excess HI

O

12. What are the products of the following reactions?

CH3 CH3

(a) CH3 – C – Cl + OCH3 (b) CH3 – C – O + CH3 – X

CH3 CH3
13. A primary alkyl bromide (A), C4H9Br, reacted with alcoholic KOH to give compound (B).
Compound (B) reacted with HBr to give an isomer of (A). When (A) was reacted with sodium
metal it gave compound (D), C8H18, which was different from the compound produced when n-
butyl bromide was reacted with sodium. Draw the structure of (A) and write equations for all the
reactions.

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 EXERCISE # III (JEE MAIN)
1. Following reaction is an example of : [AIEEE 2002]
(CH3)3C–Br + H2O  (CH3)3C–OH + HBr
(1) Elimination reaction (2) Free radical substitution
(3) Nucleophilic substitution (4) Electrophilic substitution

2. SN1 reaction is feasible in [AIEEE 2002]

Cl
(1) Cl + KOH (2) + KOH
(3) Cl + KOH  (4) CH2CH2 – Cl + KOH 

3. Bottles containing C6H5I and C6H5–CH2I lost their original labels. They were labelled A and B
for testing. A and B were separately taken in a test tube and boiled with NaOH solution. The end
solution in each tube was made acidic with dilute HNO3 and then some AgNO3 solution was
added. Substance B gave a yellow precipitate. Which one of the following statements is true for
this experiment. [AIEEE 2003]
(1) A was C6H5I (2) A was C6H5CH2I
(3) B was C6H5I (4) Addition of HNO3 was unnecessary

4. The compound formed on heating chlorobenzene with chloral in the presence of concentrated
sulphuric acid is [AIEEE 2003]
(1) Gammaxe (2) DDT (3) Freon (4) Hexa chloro ethane

5. The structure of the major product formed in the following reaction is : [AIEEE 2003]
Cl NaCN
DMF
I
CN CN Cl CN
(1) (2) (3) (4)
NC
CN CN I

6. Which of the following on heating with aqueous KOH, produces acetaldehyde? [AIEEE 2003]
(1) CH2ClCH2Cl (2) CH3CHCl2 (3) CH3COCl (4) CH3CH2Cl
7. Consider the following bromides : [AIEEE 2010]
Me Me
Me Br Me
Br Br
A B C
The correct order of SN1 reactivity is
(1) A > B > C (2) B > C > A (3) B > A > C (4) C > B > A
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8. 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields:[JEE MAIN 2016]
CH3
(a) C2H5CH2C OCH3 (b) C2H5CH2C CH2 (c) C2H5CH2 C – CH3
CH3 CH3 CH3
(1) (a) and (b) (2) All of these (3) (a) and (c) (4) (c) only

9. The product of the reaction given below is : [JEE MAIN 2016]

1. NBS/hv
X
2. H2O/K2CO3

CO2H OH O
(1) (2) (3) (4)

10. The reaction of propene with HOCl (Cl2 + H2O) proceeds through the intermediate :
(1) CH3–CHCl–CH2+ (2) CH3–CH+–CH2–OH [JEE MAIN 2016]
+ +
(3) CH3–CH – CH2–Cl (4) CH3–CH(OH)–CH2

11. The increasing order of the reactivity of the following halides for the SN1 reaction is:
[JEE MAIN 2017]
CH3CHCH2CH3 CH3CH2CH2Cl p-H3CO–C6H4–CH2Cl
Cl
(I) (II) (III)
(1) (III) < (II) < (I) (2) (II) < (I) < (III) (3) (I) < (III) < (II) (4) (II) < (III) < (I)

12. Which of the following, upon treatment with tert-BuONa followed by addition of bromine water,
fails to decolourize the colour of bromine ? [JEE MAIN 2017]
O
O C6H5 O
(1) (2) (3) (4)
Br Br Br Br

13. 3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an addition product.The
number of possible stereoisomers for the product is :- [JEE MAIN 2017]
(1) Six (2) Zero (3) Two (4) Four

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14. The major product obtained in the following reaction is :- [JEE MAIN 2017]
Br
H t
C6H5 BuOK
C6H5 
(+)

(1) (±) C6H5CH(OtBu)CH2C6H5 (2) C6H5CH=CHC6H5

(3) (+) C6H5CH(OtBu)CH2C6H5 (4) (–) C6H5CH(OtBu)CH2C6H5

15. The major product formed in the following reaction is [JEE MAIN 2018]

O HI
Heat
O

I OH I OH
(1) (2) (3) (4)
OH OH I I

16. The major product of the following reaction is : [JEE MAINS 2018]
Br
NaOMe
MeOH

OMe OMe
(1) (2) (3) (4)

17. The major product of the following reaction is: [JEE MAIN-2019]
CH3
CH3OH
CH3 – C – CHCH3
H Br
CH3 CH3
(1) CH3 – C – CHCH3 (2) CH3 – C – CH2CH3
H OCH3 OCH3
CH3 CH3
(3) CH3 – C – CH = CH2 (4) CH3 – C = CHCH3
H

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18. The increasing order of nucleophilicity of the following nucleophiles is : [JEE MAIN-2019]

(a) CH3 CO
2 (b) H2O (c) CH3 SO3 (d) O H
(1) (b) < (c) < (d) < (a) (2) (b) < (c) < (a) < (d)
(3) (a) < (d) < (c) < (b) (4) (d) < (a) < (c) < (b)

19. Increasing rate of SNl reaction in the following compounds is : [JEE MAIN-2019]
I I I I
MeO

H3C H3CO
(A) (B) (C) (D)

(1) (B) < (A) < (C) < (D) (2) (A) < (B) < (C) < (D)
(3) (B) < (A) < (D) < (C) (4) (A) < (B) < (D) < (C)

20. The major product ‗Y‘ in the following reaction is : [JEE MAIN-2019]
Cl EtONa HBr
Heat X Y
Br
HO Br
(1) (2) (3) (4)
Br

21. The major product of the following addition reaction is: [JEE MAIN-2019]
H3C – CH = CH2 
 Cl2 /H2O

O
O
(1) CH3–CH–CH2 (2) H3C–CH–CH2 (3) CH3 (4) H3C–
H3C
Cl OH OH Cl

22. An ‗Assertion‘ and a ‗Reason‘ are given below. Choose the correct answer form the following
options: [JEE MAIN-2019]
Assertion (A): Vinyl halides do not undergo nucleophilic substitution easily.
Reason (R): Even though the intermediate carbocation is stabilized by loosely held -electrons,
the cleavage is difficult because of strong bonding.
(1) (A) is a correct statement but (R) is a wrong statement.
(2) Both (A) and (R) are correct statements but (R) is not the correct explanations of (A).
(3) Both (A) and (R) are wrong statements
(4) Both (A) and (r) are correct statements and (R) is the correct explanation of (A).

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23. Which one of the following is likely to give a precipitate with AgNO3 solution?
[JEE MAIN-2019]
(1) (CH3)3CCl (2) CCl4 (3) CHCl3 (4) CH2=CH – Cl

24. What will be the major product when m-cresol is reacted with propargyl bromide
(HC C–CH2Br) in presence of K2CO3 in acetone? [JEE MAIN-2019]
OH OH
OH O
(1) (2) (3) (4)
H3C H3C
CH3 CH3

25. Heating of 2-chloro-1-phenylbutane with EtOK/EtOH gives X as the major product. Reaction of X
with Hg(OAc)2/H2O followed by NaBH4 gives Y as the major product. Y is:
[JEE MAIN-2019]

(1) (2)

(3) (4)

26. The major product of the following reaction is: [JEE MAIN-2019]

(1) (2)

(3) (4)

27. Which one of the following alkenes when treated with HCl yields majorly an anti Markovnikov
product ? [JEE MAIN-2019]
(1) F3C – CH = CH2 (2) H2N – CH = CH2
(3) CH3O – CH = CH2 (4) Cl – CH = CH2

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28. The major product of the following reaction is: [JEE MAIN-2019]
CH3CCH (i)DCl(1equic.)
(ii)DI

(1) CH3CD(I)CHD(Cl) (2) CH3CD(Cl)CHD(I)
(3) CH3CD2CH(Cl)(I) (4) CH3C(I)(Cl)CHD2

29. The major product of the following reaction is: [JEE MAIN-2019]
1. PBr3
OH 2. KOH (alc.)

OH
(1) (2) (3) (4)
HO O O O

30. The major products A and B for the following reactions are, respectively: [JEE MAIN-2019]

(1)

(2)

(3)

(4)

31. Increasing order of reactivity of the following compounds for SN1 substitution is:
[JEE MAIN-2019]

CH2–Cl Cl Cl
H3C Cl
H3CO
(A) (B) (C) (D)
(1) B < A < D < C (2) B < C < A < D (3) B < C < D < A (4) A < B < D < C

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32. The major product the following reaction is : [JEE MAIN-2019]

(1) (2)

(3) (4) 

33. The major product of the following reaction is : [JEE MAIN-2019]

(1) (2) (3) (4)

34. The major product of the following reaction is: [JEE MAIN-2019]
CH3
OH
(i) aq. NaOH
(ii) CH3I

CH3 CH3 CH3

CH3
OH OH OH
OCH3
(1) (2) (3) (4)
CH3 CH3
CH3

35. The major product of the following reaction is : [JEE MAIN-2019]

(1) (2) (3) (4)

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36. Which of the following compounds will produce a precipitate with AgNO3?[JEE MAIN-2019]

(1) (2) (3) (4)

37. The major product obtained in the following conversion is :- [JEE MAIN-2019]

(1) (2)

(3) (4)

38. The major product of the following reaction is: [JEE MAIN-2019]

(1) (2)

(3) (4)

39. The major product of the following reaction is:

(1) (2)
(3) (4)

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40. The major product of the following reaction is: [JEE MAIN-2019]

(1) (2)

(3) (4)

41. The major product in the following conversion is : [JEE MAIN-2019]

(1) (2)

(3) (4)

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 EXERCISE # IV (JEE ADVANCE-OBJECTIVE)
1. Chlorination of toluene in the presence of light and heat followed by treatment with aqueous
NaOH gives : [IIT 1990]
(A) o-cresol (B) p-cresol
(C) 2,4-dihydroxytoluene (D) Benzoic acid

2. Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl
halides due to
(A) The formation of less stable carbonium ion [IIT 1990]
(B) Resonance stabilization
(C) The inductive effect
(D) sp2 hybridised carbonattached to the halogen

3. 1-Chlorobutane on reaction with alcoholic potash gives : [IIT 1990]

(A) 1-butene (B) 1-butanol (C) 2-butene (D) 2-butanol

4. The products of reaction of alcoholic AgNO2 with ethyl bromide are [IIT 1991]
(A) Ethane (B) Ethyl nitrite (C) Nitroethane (D) Ethyl alcohol

5. Arrange the following compounds in order of increasing dipole moment [IIT 1996]
Toluene m-dichlorobenzene o-dichlorobenzene p-dichlorobenzene
I II III IV
(A) I < IV < II < III (B) IV < I < II < III (C) IV < I < III < II (D) IV < II < I < III

6. (CH3)3CMgCl reaction with D2O produces: [IIT 1997]

(A) (CH3)3CD (B) (CH3)3OD (C) (CD3)3CD (D) (CH3)3OD

7. Benzyl chloride (C6H5CH2Cl) can be prepared from toluene by chlorination with: [IIT 1998]
(A) SO2Cl2 (B) SOCl2 (C) Cl2,(hv) (D) NaOCl

8. The order of reactivity of the following alkyl halides for a SN2 reaction is: [IIT 2000]
(A) R–F > R–C > R–Br > R–I (B) R–F > R–Br > R–Cl > R–I
(C) R–Cl > R–Br > RF > RI (D) R–I > RBr > R–Cl > R–F

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9. Which of the following has the highest nucleophilicity? [IIT 2000]
(A) F– (B) OH– (C) CH3 (D) NH 2

10. An SN2 reaction at an asymmetric carbon of a compound always gives. [IIT 2001]
(A) an enantiomer of the substance (B) a product with opposite optical rotation
(C) a mixture of diasteremoers (D) a single stereoisomer

11. The compound that will react most readily with NaOH to form methanol is [IIT 2001]
(A) (CH3)4N+I– (B) CH3OCH3 (C) (CH3)3S+I– (D) (CH3)3Cl

12. Identify the set of reagents / reaction conditions 'X' and 'Y' in the following set of transformation:
CH3 – CH2 –CH2Br 
X
 Product 
Y
 CH3 – CH – CH3 [IIT 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 = concentrated alcoholic NaOH, 80°C; Y = Br2/CHCl3, 0°C

13. CH 3 MgBr + Ethyl ester  which can be formed as product. [IIT 2003]
excess

CH2CH3 CH3CH3
(A) HO CH2CH3 (B) HO CH2CH2CH3
CH2CH3 CH2CH3

CH2CH3 CH3
(C) HO CH2CH3 (D) HO CH3
CH3 CH3

14. The product of following reaction is [IIT 2003]

OH

C2H5O–(excess)
+ C2H5I C2H5OH

(A) C6H5OC2H5 (B) C2H5OC2H5 (C) C6H5OC6H5 (D) C6H5I

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15. The following compound on hydrolysis in aqueous acetone will give: [IIT 2005]
CH3 H CH3

MeO NO2

H Cl CH3
CH3 H CH3

(K) MeO NO2

H OH CH3
CH3 H CH3

(L) MeO NO2

OH H CH3
CH3 H CH3

(M) MeO NO2

H CH3 OH
It mainly gives
(A) K and L (B) Only K (C) L and M (D) Only M

16. Match the following: [IIT 2006]

Column-I Column-II
(A) CH3–CHBr–CD3 on treatment with alc. KOH gives (P) E1 reaction
CH2=CH–CD3 as a major product.
(B) Ph – CHBr - CH3 reacts faster than Ph-CHBr-CD3. (Q) E2 reaction
(C) Ph-CD2-CH2Br on treatment with C2H5OD/C2H5O– (R) E1cb reaction
gives Ph-CD=CH2 as the major product.
(D) PhCH2CH2Br and PhCD2CH2Br react with same rate. (S) First order reaction

17. The major product of the following reaction is [IIT 2008]

H3C Br
F
PhSNa
dim ethyl formamide

NO2
HC
3
SPh H3C SPh H3C Br H3C SPh
F F SPh SPh
(A) (B) (C) (D)

NO2 NO2 NO2 NO2

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18. In the reaction OCH2 HBr the products are [IIT 2010]

(A) Br OCH3 and H2 (B) Br and CH3Br

(C) Br and CH3OH (D) OH and CH3Br

19. KI in acetone, undergoes SN2 reaction with each of P, Q, R and S. The rates of the reaction vary as
[IIT 2013]
O
Cl
H3C–Cl Cl Cl

P Q R S
(A) P > Q > R > S (B) S > P > R > Q (C) P > R > Q > S (D) R > P > S > Q

20. The reactivity of compound Z with different halogens under appropriate conditions is given below
OH Mono halo substituted derivative when X2=12
X2
di halo substituted derivative when X2=Br2
C(CH3)3
tri halo substituted derivative when X2=Cl2
The observed pattern of electrophilic substitution can be explained by [IIT 2014]
(A) The steric effect of the halogen
(B) The steric effect of the tert-butyl group
(C) The elctronic effect of the phenolic group
(D) The electronic effect of the turt-butyl group

21. In the following reaction, the major product is [IIT 2015]

CH3
1 equivalent HBr
CH2
H2C
CH3 CH3 CH3 CH3
CH3 CH2
(A) CH2 (B) H3C (C) H2C Br (D) H3C Br
Br Br

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22. The correct statement(s) for the following addition reactions is (are) [IIT 2017]
H3C H Br2 /CHCl3
(i) M and N
H CH3
H3C CH3 Br2 /CHCl3
(ii) O and P
H H
(A) (M and O) and (N and P) are two pairs of diastereomers
(B) Bromination proceeds through trans-addition in both the reactions
(C) O and P are identical molecules
(D) (M and O) and (N and P) are two pairs of enantiomers

23. For the following compounds, the correct statement(s) with respect to nucleophilic substitution
reactions is (are) [IIT 2017]
CH3 CH3
Br Br
CH3–C–Br Br
CH3
I II III IV
(A) Compound IV undergoes inversion of configuration
(B) The order of reactivity for I, III and IV is : IV > I > III
(C) I and III follow SN1 mechanism
(D) I and II follow SN2 mechanism

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 EXERCISE # V (JEE ADVANCE-SUBJECTIVE)
1. Fill in the blanks :
(a) Butane nitrile can be prepared by heating _____with alcoholic KCN. [IIT 1992]
(b) Amongst three isomers of nitrophenol, the one that is least soluble in water is____

2. Arrange the following in order of their

(i) Increasing basicity
– –
H2O, OH , CH3OH, CH3O
(ii) Increasing reactivity in nucleophilic substitution reactions
CH3F, CH3I, CH3Br, CH3Cl [IIT 1992]

3. Write the structures of the major organic product expected from each of the following reactions:
[IIT 1992]
CH3
(i) H3C CH2CH3 Alc. KOH (ii) CH3CH2CHCl2 
aq.alkali
boil

Cl
4. Identify the major product in the following reaction. [IIT 1993]
H
C6H5—CH2 CH3 
Alc.KOH

 ?  
HBr
?
Br
5. Identify the major product in the following reactions : [IIT 1993]
Cl
(i) C6H5 – CH2 – CH – CH3  
alcoholic
KOH 
 ?  
HBr
? (ii) C6H5COOH + CH3Mgl  ? + ?

6. Aryl halides are less reactive than alkyl halides towards nucleophilic reagents. Give reason.
[IIT 1994]

7. Draw the stereochemical structure of product in the following reaction. [IIT 1994]
CH3
Br H NaOH
SN2

C2H5

8. Optically active 2-iodobutane on treatment with NaI in acetone gives a product which does not
show optical activity. Explain briefly. [IIT 1995]

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9. An alkyl halide X of formula C6H13Cl on treatment with potassium tertiary butoxide gives two
isomeric alkenes Y and Z (C6H12). Both alkenes on hydrogenation give 2,3–dimethylbutane.
Predict the structures of X, Y and Z. [IIT 1996]

10. Predict the structure of the intermediates/products in the following reaction sequence-
[IIT 1996]
Br
H Ph NaI
MeO H Acetone C
Ph
11. Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(CH3)3 CBr + NaOMe  or CH3Br + NaO-t-Bu   [IIT 1997]

12. Write the structures of the products: [IIT 1998]

C6H5CH2CHClC6H5

C6H5
13. (a) C6H5CH2CHCl 
alc. KOH
Heat
 A + B Write structures of (A) and (B).
(b) (CH3)2CHOCH3 
HI(excess)
Heat
 A + B Write structures of A and B. [IIT 1998]

14. Complete the following reaction with appropriate structures of products/reagents. [IIT 1998]
CH=CH2
Br2 (i) NaNH2 (3 equi.)
(A) (B)
(ii) CH3I

15. What would be major product? [IIT 2000]

CH3
C2H5OH
CH3 – C – CH2Br ?

CH3

16. Identify X, Y and Z in the following synthetic scheme and write their structures [IIT 2002]
 X   Y 
H2 /Pd–BaSO4
CH3CH2CCH  (i) NaNH2
(ii)CH CH Br
alkaline
KMnO
Z
3 2 4

17. Give major products A, B, C and D in following reaction sequence. [IIT 2004]
CH2–Cl
KCN (i) NaOEt / EtOH H3O
(A) (B) (C)
DMF (ii) PhCHO / 
(i) SOCl3
(D)
(ii) CH3NH2

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18. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane
using alcoholic KOH is [IIT 2011]

19. The maximum number of isomers (including stereoisomers) that are possible on mono-
chlorination of the following compounds, is [IIT 2011]
CH3
C
CH3CH2 CH2CH3
H

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 ANSWER KEY
EXERCISE # I (MAINS ORIENTED)
1. A 2. B 3. B 4. C 5. A 6. C 7. A
8. C 9. B 10. C 11. B 12. C 13. A 14. C
15. A 16. D 17. C 18. B 19. B 20. C 21. C
22. D 23. A 24. B 25. A 26. ABCD 27. D 28. B
29. C 30. B 31. C 32. C 33. A 34. B 35. A
36. A 37. D 38. C 39. C 40. C 41. B 42. B

EXERCISE # II-A
1. ABCD 2. BD 3. ABCD 4. AC 5. AD 6. B 7. AC
8. D 9. AC 10. ABD 11. ABCD 12. AD 13. ABCD 14. ABC
15. CD 16. ABCD 17. C

EXERCISE # II-B
1. C 2. C 3. (A)  P,R ; (B)P,Q ; (C)P; (D)P,Q
4. (A)Q ; (B)P ; (C)S ; (D)R 5. (A)S; (B)Q; (C)R; (D) P
6. (A)S; (B)R,S; (C)R; (D)P, Q
7. (A) P,Q,R,S; (B)P,R; (C)T; (D)Q,S;
8. (A)Q,S; (B)P,R,S; (C)P,R,S; (D)P,Q,R,S
9. Molecule A, C6H11Br has 1 unsaturation

Alc. KOH

A single possible product , it suggests a symmetrical arrangement

So, E =
CH2Br
There are only two possibilities of Br structure I can be resolved
(I) (II)
while structure II cannot be resolved so 'A' :

Br HBr, Peroxide
Br
(A) Br
resolvable product
(C)

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 33

33 33
10. The elimination of HI (or DI) in presence of strong base shows E2 elimination. The rate
determining step involves breaking up of C–H (or C–D) bond. The C–D bond being stronger than
C–H and thus elimination is faster in case of CH3 – CH2I.

HI (excess)
11. 
O I I
12. Not available.
CH3 CH3
alc KOH
13. CH3 C CH3 Br CH3 C CH2
HBr
H
CH3
CH3 C – CH3
Br
Na / Diethylether

CH3 CH3
HC
3 C C CH3
CH3 CH3

EXERCISE # III (JEE MAIN)

1. 3 2. 1 3. 1 4. 2 5. 4 6. 2 7. 2
8. 2 9. 3 10. 3 11. 2 12. 1 13. 4 14. 2
15. 1 16. 3 17 2 18. 4 19. 1 20. 4 21. 2
22. 1 23. 1 24. 4 25. 4 26. 2 27. 1 28. 4
29. 2 30. 1 31. 1 32. 4 33. 3 34. 1 35. 2
36. 4 37. 4 38. 2 39. 4 40. 4 41. 4

EXERCISE # IV (JEE-ADVANCE-OBJECTIVE)
1. D 2. BD 3. A 4. C 5. B 6. A 7. AC
8. D 9. C 10. D 11. A 12. B 13. D 14. B
15. A 16. (A)Q; (B)Q; (C)R,S; (D)P,S 17. A 18. D 19. B
20. ABC 21. D 22. AB 23. (ACD) or (ABCD)

C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Mob. 0744-2799900 www.nucleuseducation.in 34

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