(Organic Chemistry) SUBSTITUTION ELIMINATION

EXERCISE - I (MAINS ORIENTED)

1. Major product of following reaction is:

(A) (B)

(C) (D)

2. Which compound undergoes hydrolysis by the SN 1 mechanism at the fastest rate?

(A) (B)

(C) (D)
3. Arrange the following compounds in decreasing order of their reactivity for hydrolysis reaction

(I) C6 H5 − CH2 − Br (II) (II) (II)

(A) I > II > III > IV (B) IV > II > I > III
(C) III > IV > II > I (D) IV > III > II > I
4. Arrange the following compounds in order of decreasing rate of hydrolysis for SN 1 reaction:

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

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5. Which of the following is most reactive toward SN 1 reaction?

(I) (II)

(III) (IV)

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

6. Arrange the following compounds in order of decreasing rate of hydrolysis for SN 1 reaction:

(A) (B)

(C) (D)

7. Consider the SN 1 solvolysis of the following halides in aqueous formic acid, decide decreasing
order of reactivity of above alkyl halide?

(I) (II)

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(III) (IV)

(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?

(A) (B)

(C) (D)

9. Major product of following reaction is:

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(C) (B) (C) (D) None of these

10. If 96% racemisation takes place in given reaction then find out the correct statement:

(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 :

(A) CH3 − CH = CH − CH2 − Br (B)

(C) CH2 = CH − CH = CH2 (D)

12. Which of the following can not give SN 1 reaction easily?

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

13. Which one of the following compounds will be most reactive for SN 1 reactions?

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14. Which of the following compounds is most rapidly hydrolysed by SN 1 mechanism?
(A) C6 H5 Cl (B) Cl − CH2 − CH = CH2
(C) (C6 H5 )3 CCl (D) C6 H5 CH2 Cl

15. Among the bromides I − III given below, the order of reactivity in SN 1 reaction is:

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

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

16. Which of the following is most reactive toward SN 2.

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

17. Which of the following is most reactive toward SN 2.

CH3 Br + OH − ⟶ CH3 OH + Br −
(A) Rate = k[CH3 Br] (B) Rate = k[OH − ]
(C) Rate = k[CH3 Br][OH − ] (D) Rate = k[CH3 Br]o [OH − ]o

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

Br − + CH3 OH ⟶ 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:

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

20. The reactivity of given compounds towards SN 2 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 :

(A) I can't be SN 1 (B) II can't be SN 2

(C) I can be SN 1& II can be SN 2 (D) I can be SN 2& &I can be SN 1

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

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

23. Arrange these compounds in order of increasing SN 2 reaction rate :

(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?

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(A) (B)

(C) (D)

25. The major product in the given reaction is:

(A) (B)

(C) (D) All of these

26. The compound CH3 − O − CH2 − Br gives faster rate of nucleophilic substitution reaction than :
(A) CH3 Br (B) CH3 CH2 Br
(C) PhCH2 Br (D) CH3 OCH2 Cl

27. Which will give white ppt. with AgNO3 ?

(A) (B)

(C) (D) Both (A) and (C)

28. When ethyl bromide is treated with moist Ag 2 O, the main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these

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29. When ethyl bromide is treated with dry Ag 2 O, the main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these

30. Major product of following reaction is:

(A) (B) (C) H2 C = CH2 (D)

31. Which reaction conditions (reagents) is suitable for the following reaction:

Br
(A) CCl2 (B) SOBr2 (C) PBr3 (D) HBr/ conc H2 SO4
4

32. Major product of following reaction is:

(A) (B)

(C) (D)

33. Assuming all the substrate convert into substitution products containing 0.05 mole of
Configuration, calculate the percentage of SN 2 mechanism.

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(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 occur via intermediate formation of an alkyl chloro sulphite

35. Major product of following reaction is:

(A) (B) (C) H2 C = CH2 (D)

35. In the given pairs, which pair represent correct order of rate dehydrohalogenation reaction.

(A) (B)

(C) (D) CH3 − CH2 − Cl < CD3 − CD2 − Cl

36. Major product of following reaction is:

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(A) (B)

(C) (D)

38. Major product of following reaction is:

(A) (B)

(C) (D)

39. CORRECT order of rate of reaction for following compounds with Conc. HBr is:
CH3 OH CH3 CH2 OH (CH3 )2 CHOH (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

40. If P&Q are the major products then P&Q are respectively:
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(A) (B)

(C) (D)

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:

(A)

(B)

(C) (D)

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EXERCISE # II-A
1. Rate of SN 2 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 SN 2
reaction.

(A)

(B)

(C)

(D)

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

(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 "

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4. Which of the following statements is / are true?
(A) CH3 − CH2 − CH2 − I will react more readily than (CH3 )2 CHI for SN 2 reactions.
(B) CH3 − CH2 − CH2 − Cl will react more readily than CH3 − CH2 − CH2 − Br for SN 2 reaction.
(C) CH3 − CH2 − CH2 − CH2 − Br will react more readily than (CH3 )3 C − CH2 − Br for SN 2
reactions
(D) CH3 − O − C6 H4 − CH2 Br will react more readily than NO2 − C6 H5 − CH2 Br for SN 2
reaction

5. Incorrect statement about alkyl halides is / are:

(A) Tertiary alkyl halides undergo SN 2 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

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

(A) (B)

(C) (D)

7. SN 1& SN 2 is not favourable in

(A) H2 C = CH − Cl (B) Ph − CH2 − Cl
(C) Ph − Cl (D) H2 C = 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.

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9. In which of the following reaction(s), configuration about chiral carbon is retained in the major
product

(A) (B)

(C) (D)

10. A gem dichloride is formed in the reaction:

(A) CH3 CHO and PCl5 (B) CH3 COCH3 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)?

(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

12. Which of following are correct for given reaction

(A) Major product of reaction is

(B) Major product is
(C) Major product formation involve substitution
(D) The reaction is E2 reaction

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13. Which of the following reactions is (are) incorrectly matched with their major product:
HI
(A) Me3 C − O − CH3 ⟶ Me3 C − OH + CH3 I
HI
(B) H3 C − O − CH2 − CH3 ⟶ CH3 OH + ICH2 CH3

(C)

H3 O + 18
(D) CH3 − O − CH2 CH3 ⟶ CH3 OH + CH3 CH2 O H

14. Correct statement among the following is/are:

(A) The rate of hydrolysis of tertiary butyl bromide increases by addition of Ag 2 O
(B) Aqueous Ag 2 O produces nucleophilic OH −
(C) The addition of a small amount of oxygen slows down the photochemical chlorination of
methane.
(D) CH3 CH2 Cl is more reactive than PhCH2 Cl 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 H2 SO4
(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

16. From left to right, correct statements are:

(A) Rate of SN 1 mechanism increases in polar protic solvent

(B) Rate of SN 2 mechanism increases in DMSO
(C) Rate of E2 mechanism increases
(D) Rate of E1 mechanism increases

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17. How many monobromo derivatives are possible for Hydrocarbon (R)?

(A) 2 (B) 3 (C) 5 (D) 1

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EXERCISE # II-B
COMPREHENSION TYPE
Paragraph for Q. No. 01 to 02
Groups like CN&[−O − N̈ = 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 [C ≡ N ⟷: C = N ⊖ ] . Similarly nitrite ion also

represents an ambident nucleophile with two different points of linkage [O−= O].
1. Correct option among the following:

(A) (B)

(C) (D)

2. Incorrect statement

(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) (P) Elimination Reaction

(B) (Q) Carbocation

(C) (R) Carbanion

(D) (S) Free radical

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4. Match the List I with List II
List-I List-II
(Reactions) (Products)
⊖
(A) CH3 − O − SO2 CH3 + C2 H5 O (P) CH3 − CH2 − PH2
(B) CH3 − CH2 − I + PH3 (Q) CH3 − O − C2 H5
⊖⊕
(C) HC ≡ C Na + CH3 − CH2 − Br (R) CH3 − O − CH3
Θ
(D) CH3 − Cl + CH3 − O (S) CH ≡ C − CH2 − CH3

5. Match the List I with List II

⊖
Z − CH2 Br + CH3 O ⟶ Z − CH2 − OCH3 + Br Θ
List-I (Z-) List-II (Relative reactivity)
(A) H − (P) 0.1
(B) CH3 − (Q) 3
(C) C2 H5 − (R) 1

(D) (S) 100

6. Match the List I with List II

List-I List-II

(A) E1CB (P)

(B) Saytzeff alkene as major product (Q)

(C) E2 (R)

(D) Ei (S)

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7. Column-I Column-II
(Reactions) (Characteristics)
HBr
(A) CH3 CH2 CH = CH2 ⟶ (P) Bimolecular
HBr, Peroxide
(B) CH3 CH2 CH = CH2 ⟶ (Q) Carbocation intermediate
SOCl2
(C) PhCH(CH3 )OH ⟶ (R) Regioselective
HBr
(D) PhCH(CH3 )OH ⟶ (S) Racemic modification
(T) Stereospecific reaction

8. Column-I Column-II
(Statements) (Consistent path of reaction)
(A) Reactions are concerted (P) SN 1
(B) CH3 X cannot react (Q) SN 2
(C) 3∘ R − X > 2∘ R − X > 1∘ R − X (R) E1
(D) R − I reacts faster than R − Cl (S) E2

9.

Identify A, C&E in the sequence of reaction.

10. CH3 − CH2 I reacts more rapidly with strong base in comparison to CD3 CH2 I.

11. Predict the product(s) and write the mechanism of the given reaction:

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12. What are the products of the following reactions?

(A) (B)

13. A primary alkyl bromide (A), C4 H9 Br, 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), C8 H18 , 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 )3 C − Br + H2 O ⟶ (CH3 )3 C − OH + HBr

(A) Elimination reaction

(B) Free radical substitution
(C) Nucleophilic substitution
(D) Electrophilic substitution

2. SN 1 reaction is feasible in [AIEEE 2002]

(A)

(B)

(C)

(D)

3. Bottles containing C6 H5 I and C6 H5 − CH2 I 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]
(A) A was C6 H5 I (B) A was C6 H5 CH2 I
(C) B was C6 H5 I (D) Addition of HNO3 was unnecessary

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

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5. The structure of the major product formed in the following reaction is: [AIEEE 2003]

(A) (B)

(C) (D)

6. Which of the following on heating with aqueous KOH, produces acetaldehyde? [AIEEE 2003]
(A) CH2 ClCH2 Cl (B) CH3 CHCl2 (C) CH3 COCl (D) CH3 CH2 Cl

7. Consider the following bromides: [AIEEE 2010]

The correct order of SN 1 reactivity is

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

8. 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields:

[JEE MAIN 2016]

(A) (a) and (b) (B) All of these

(C) (a) and (c) (D) (c) only

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

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

10. The reaction of propene with HOCl(Cl2 + H2 O) proceeds through the intermediate:
[JEE MAIN 2016]
(A) CH3 − CHCl − CH2+ (B) CH3 − CH + − CH2 − OH
(C) CH3 − CH + − CH2 − Cl (D) CH3 − CH(OH) − CH2+

11. The increasing order of the reactivity of the following halides for the SN 1 reaction is:
[JEE MAIN 2017]

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

(A) (B)

(C) (D)

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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]
(A) Six (B) Zero (C) Two (D) Four

14. The major product obtained in the following reaction is :- [JEE MAIN 2017]

(A) (±)C6 H5 CH(Ot Bu)CH2 C6 H5 (B) C6 H5 CH = CHC6 H5

(C) (+)C6 H5 CH(Ot Bu)CH2 C6 H5 (D) (−)C6 H5 CH(O𝑡 Bu)CH2 C6 H5

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

(A) (B)

(C) (D)

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

(A) (B)

(C) (D)

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

(A) (B)

(C) (D)

18. The increasing order of nucleophilicity of the following nucleophiles is : [JEE MAIN-2019]
⊖
(a) CH3 COΘ2 (b) H2 O (c) CH3 SOΘ
3 (d) O H
(A) (b) < (c) < (d) < (a) (B) (b) < (c) < (a) < (d)
(C) (a) < (d) < (c) < (b) (D) (d) < (a) < (c) < (b)

19. Increasing rate of 𝑆𝑁 𝑙 reaction in the following compounds is: [JEE MAIN-2019]

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

20. The major product 'Y' in the following reaction is: [JEE MAIN-2019]

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

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21. The major product of the following addition reaction is: [JEE MAIN-2019]
Cl2 /H2 O
H3 C − CH = CH2 ⟶
(A) (B)

(C) (D)

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 𝜋-electrons,
the cleavage is difficult because of strong bonding.
(A) (A) is a correct statement but (R) is a wrong statement.
(B) Both (A) and (R) are correct statements but (R) is not the correct explanations of (A).
(C) Both (A) and (R) are wrong statements
(D) Both (A) and (r) are correct statements and (R) is the correct explanation of (A).

23. Which one of the following is likely to give a precipitate with AgNO3 solution?
[JEE MAIN-2019]
(A) (CH3 )3 CCl (B) CCl4 (C) CHCl3 (D) CH2 = CH − Cl

24. What will be the major product when m-cresol is reacted with propargyl bromide
(HC ≡ C − CH2 Br) in presence of K 2 CO3 in acetone? [JEE MAIN-2019]

(A) (B)

(C) (D)

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25. Heating of 2-chloro-1-phenylbutane with EtOK/EtOH gives X as the major product. Reaction of
X with Hg(OAc)2 /H2 O followed by NaBH4 gives Y as the major product. Y is:[JEE MAIN-2019]

(A) (B)

(C) (D)

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

(A) (B)

(C) (D)

27. Which one of the following alkenes when treated with HCl yields majorly an anti Markovnikov
product? [JEE MAIN-2019]
(A) F3 C − CH = CH2 (B) H2 N − CH = CH2
(C) CH3 O − CH = CH2 (D) Cl − CH = CH2

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

(A) CH3 CD(I)CHD(Cl) (B) CH3 CD(Cl)CHD(I)

(C) CH3 CD2 CH(Cl)(I) (D) CH3 C(I)(Cl)CHD2

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

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

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

(A)

(B)

(C)

(D)

31. Increasing order of reactivity of the following compounds for SN 1 substitution is:
[JEE MAIN-2019]

(A) B < A < D < C (B) B < C < A < D (C) B < C < D < A (D) A < B < D < C
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32. The major product the following reaction is: [JEE MAIN-2019]

(A) (B)

(C) (D)

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

(A) (B)

(C) (D)

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

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

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

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

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

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

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

(A) (B)

(C) (D)

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

(A) (B)

(C) (D)

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

(A) CH3 CH = CHCH2 NH2 (B) CH3 CH = C = CH2

(C) (D) CH3 CH2 C ≡ CH

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

(A) (B)

(C) (D)

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

(A)

(B)

(C)

(D)

42. [JEE MAIN-2020]

Compound X will be:

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

43. The correct order of reactivity of the given chlorides with acetate in acetic acid is:

[JEE MAIN-2021]

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(A)

(B)

(C)

(D)

44. [JEE MAIN-2021]

The product " A " and "B" formed in above reactions are

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45. The product formed in the first step of the reaction of [JEE MAIN-2021]

with excess Mg/Et 2 O(Et = C2 H5 ) is:

(A)

(B)

(C)

(D)

46. The major product (P) in the reaction [JEE MAIN-2022]

[Ph is −C6 H5 ] is

(A) (B)

(C) (D)

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47. [JEE MAIN-2022]

In the above reaction ‘A’ is

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

48.

The stable carbocation formed in the above reaction is: [JEE MAIN-2022]

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

49. Decreasing order towards 𝑆𝑁 1 reaction for the following compounds is:

[JEE MAIN-2023]

(A) a > c > d > b (B) a > b > c > d

(C) b > d > c > a (D) d > b > c > a

APNI KAKSHA 35
(Organic Chemistry) SUBSTITUTION ELIMINATION
50. The correct order of melting point of dichlorobenzenes is [JEE MAIN-2023]

(A) (B)

(C) (D)

APNI KAKSHA 36
(Organic Chemistry) SUBSTITUTION ELIMINATION
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 [IIT 1990]
(A) The formation of less stable carbonium ion
(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 )3 CMgCl reaction with D2 O produces: [IIT 1997]

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

7. Benzyl chloride (C6 H5 CH2 Cl) can be prepared from toluene by chlorination with:[IIT 1998]
(A) SO2 Cl2 (B) SOCl2 (C) Cl2 , (hv) (D) NaOCl

8. The order of reactivity of the following alkyl halides for a SN 2 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

APNI KAKSHA 37
(Organic Chemistry) SUBSTITUTION ELIMINATION
9. Which of the following has the highest nucleophilicity? [IIT 2000]
(A) F − (B) OH − (C) CH3− (D) NH2−

10. AnSN 2 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 )4 N+ I− (B) CH3 OCH3 (C) (CH3 )3 S+ I− (D) (CH3 )3 Cl

12. Identify the set of reagents / reaction conditions ' X ' and ' Y ' in the following set of
transformation: [IIT 2002]

(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. CH3 MgBr + Ethyl ester → which can be formed as product. [IIT 2003]
excess

(A) (B)

(C) (D)

APNI KAKSHA 38
(Organic Chemistry) SUBSTITUTION ELIMINATION
14. The product of following reaction is [IIT 2003]

(A) C6 H5 OC2 H5 (B) C2 H5 OC2 H5 (C) C6 H5 OC6 H5 (D) C6 H5 I

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

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 CH2 = CH − (A) E1 reaction
CD3 as a major product.
(B) Ph − CHBr − CH3 reacts faster than Ph − CHBr − CD3 . (B) E2 reaction
(C) Ph − CD2 − CH2 Br on treatment with C2 H5 OD/C2 H5 O− gives Ph − (C) E1cb reaction
CD = CH2 as the major product.
(D) PhCH2 CH2 Br and PhCD2 CH2 Br react with same rate. (D) First order
reaction

APNI KAKSHA 39
(Organic Chemistry) SUBSTITUTION ELIMINATION
17. The major product of the following reaction is [IIT 2008]

(A) (B)

(C) (D)

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

(A) (B)

(C) (D)

19. KI in acetone, undergoes SN 2 reaction with each of P, Q, R and S. The rates of the reaction vary
as [IIT 2013]

(A) P > Q > R > S (B) S > P > R > Q (C) P > R > Q > S (D) R > P > S > Q
APNI KAKSHA 40
(Organic Chemistry) SUBSTITUTION ELIMINATION
20. The reactivity of compound Z with different halogens under appropriate conditions is given
below [IIT 2014]

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]

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

22. The correct statement(s) for the following addition reactions is (are) [IIT 2017]

(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

APNI KAKSHA 41
(Organic Chemistry) SUBSTITUTION ELIMINATION
23. For the following compounds, the correct statement(s) with respect to nucleophilic
substitution reactions is (are) [IIT 2017]

(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 SN 1 mechanism
(D) I and II follow SN 2 mechanism

24. The major product formed in the following reaction of [IIT 2021]

(A)

(B)

(C)

(D)

APNI KAKSHA 42
(Organic Chemistry) SUBSTITUTION ELIMINATION
25. In the following reactions, P, Q, R, and S are the major products. [IIT 2023]

The correct statement about P, Q, R, and S is:

(A) P is a primary alcohol with four carbons.
(B) Q undergoes Kolbe's electrolysis to give an eight-carbon product.
(C) R has six carbons and it undergoes Cannizzaro reaction.
(D) S is a primary amine with six carbons.

APNI KAKSHA 43
(Organic Chemistry) SUBSTITUTION ELIMINATION
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

H2 O, OH − , CH3 OH, CH3 O−

(ii) Increasing reactivity in nucleophilic substitution reactions

CH3 F, CH3 I, CH3 Br, CH3 Cl [IIT 1992]

3. Write the structures of the major organic product expected from each of the following
reactions: [IIT 1992]

(i) (ii)

4. Identify the major product in the following reaction. [IIT 1993]

5. Identify the major product in the following reactions: [IIT 1993]

(i) (ii) C6 H5 COOH + CH3 Mgl →? +?

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

APNI KAKSHA 44
(Organic Chemistry) SUBSTITUTION ELIMINATION
7. Draw the stereochemical structure of product in the following reaction. [IIT 1994]

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

9. An alkyl halide X of formula C6 H13 Cl on treatment with potassium tertiary butoxide gives two
isomeric alkenes Y and Z(C6 H12 ). 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]

11. Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(CH3 )3 CBr + NaOMe ⟶ or CH3 Br + NaO − t − Bu ⟶ [IIT 1997]

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

C6 H5 CH2 CHClC6 H5

13. (a)

(b) [IIT 1998]

APNI KAKSHA 45
(Organic Chemistry) SUBSTITUTION ELIMINATION
14. Complete the following reaction with appropriate structures of products/reagents. [IIT 1998]

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

16. Identify X, Y and Z in the following synthetic scheme and write their structures [IIT 2002]

17. Give major products A, B, C and D in following reaction sequence. [IIT 2004]

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
monochlorination of the following compounds, is [IIT 2011]

APNI KAKSHA 46
(Organic Chemistry) SUBSTITUTION ELIMINATION
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.

APNI KAKSHA 47
(Organic Chemistry) SUBSTITUTION ELIMINATION
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 − CH2 I.

11.
12. Not available.
13.

EXERCISE # III (JEE MAIN)

1. C 2. A 3. A 4. B 5. D 6. B 7. B
8. B 9. C 10. C 11. B 12. A 13. D 14. B
15. A 16. C 17. B 18. D 19. A 20. D 21. B
22. A 23. A 24. D 25. D 26. B 27. A 28. D
29. B 30. A 31. A 32. D 33. C 34. A 35. B
36. D 37. D 38. B 39. D 40. D 41. D 42. D
43. A 44. C 45. C 46. C 47. C 48. C 49. C
50. D
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) 24. B 25. B

APNI KAKSHA 48