1. Which of the SN2 reaction is fastest?

(a) CH3Br + HC C–  CH3C CH + Br–

(b) CH3Br + HCCH CH3C CH + HBr
(c) CH3CH2Br + HCC–  CH3CH2CCH + Br–
(d) CH3CH2Br + HC CH  CH3CH2C CH + HBr

2. Which statement is true about SN2 mechanism-

(a) The rate of reaction increases on increasing strength of the nucleophile
(b) The reaction is faster in polar aprotic solvents
(c) The rate of reaction increases as the leaving group ability increases
(d) All of the above

3. A correct statement about transition state of SN2 reaction is-

(a) The transition state proceeds and follow an unstable reaction intermediate
(b) The transition state will always have net negative charge
(c) Existence of this state implies an exothermic reaction
(d) The single transition state represents the point of maximum free energy of the reaction

4. What is the correct increasing order of reactivity of the followings in SN2 reaction?
(I) CH2 = CH – CH2 – Br (II) CH2 = CH – I
(III) CH3CH2CH2 – I (IV) CH3OCH2CH2 – I
(a) I < II < III < IV (b) III < II < I < IV (c) II < III < IV < I (d) II < I < III < IV

5. What is the correct increasing order of reactivity of the following in the SN2 reaction-
(I) (CH3)2CCH2Cl (II) CH3CH2CH(Cl)CH3
(III) C6H5Cl (IV) p-O2N – C6H4 – CH2Cl
(a) I < II < III < IV (b) III < II < I < IV (c) II < III < IV < I (d) III < I < II < IV

6. Consider the two lines shown in the diagram given below :

In a SN2 reaction, these two lines compare the effect of the-

(a) Substrate (b) Nucleophile (c) Leaving group (d) Substrate or nucleophile

7. The correct statement concerning a SN2 reaction is-

(a) The reaction mechanism involve atleast one reactive intermediate
(b) Transition state is pentavalent
(c) Product is formed after passing through several transition states
(d) Nucleophile attacks from front side on which leaving group is present
8. CH3CH2Cl + KOH(aq.) CH3CH2—OH + KCl The above reaction is
(1) Nucleophilic substitution (2) Electrophilic substitution
(3) Free - radical substitution (4) Nucleophilic addition
9. Heating together of sodium ethoxide and ethyl iodide will give
(1) Ether (2) Ethyl alcohol (3) Acetaldehyde (4) Acetic acid

3 2 1
10. aq. KOH
CH3 CH CH2Cl  CH3 CH CH2 OH
CH3 CH3

In the above reaction the attack of a nucleophile would be from which side
(1) On the front side of Cl of C1 carbon (2) On C2 carbon
(3) On the rear side of Cl of C1 carbon (4) On C3 carbon

11. In a SN2 substitution reaction of the type

R—Br + Cl  R –Cl +Br , which one of the following has the highest relative rate ?
DMF

CH3 CH3
(1) CH3 CH CH2Br (2) CH3 C CH2Br
CH3
(3) CH2—CH2Br (4) CH3—CH2—CH2Br
H H
CH3(CH2)5  (CH2)CH
5 3
OH
12. Following reaction is C Br  HO C
H3C CH3
(1) E 1
(2) SN 1
(3) E 2
(4) SN2
13. What would be the product when tert. butyl chloride reacts with sodium ethoxide
(1) t– butyl alcohol (2) t– butyl ethyl ether (3) iso butyl ethyl ether (4) isobutylene

14. Which of the following is the correct order of decreasing SN2 reactivity ? (X = a halogen)
(A) RCH2X > R3CX > R2CHX (B) RCH2X > R2CHX > R3CX
(C) R3CX > R2CHX > RCH2X (D) R2CHX > R3CX > RCH2X

15. The organic chloro compound, which shows complete/maximum stereochemical inversion during a SN2 reaction ,
(A) (CH3)3CCl (B) (CH3)2CHCl (C) CH3Cl (D) (C2H5)2CHCl

16. The products of reaction of alcoholic silver nitrite with ethyl bromide are -
(A) Ethane (B) methyl nitrite (C) Nitroethane (D) Ethyl alcohol

17. The order of reactivity of the following alkyl halides for a SN2 reaction is –
(A) R F > RCl > R–Br > R–I (B) R–F > R–Br > R–Cl > R–I
(C) R–Cl > R–Br > RF > RI (D) R–I > R Br > R–Cl > R–F

18. Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of –
(A) instability (B) insolubility (C) steric hindrance (D) inductive effect

19. In the following reaction Br + HC  C N a  the substrate is transformed into

(A) C  CH (B) = CH2 (C) (D) C  C — CH3

20. Which of the following reactions is expected to take place by S N2 mechanism ?

CH3
| H2O
(A) CH3 — CH2 — C — Br  AgOH  H 2O
(B) (CH3 )3 C — Br  KOH  
|
CH3
CH3CO 2H dim ethyl sulphoxide
(C) CH3 CH2CHBrCH 3  CH3 CO 2Na    (D) (CH3 )2 CHBr  AgCN   

21. Neopentyl bromide is allowed to react with sodium ethoxide in ethanol The major product formed in the
reaction is

CH3 CH3
| |
(A) CH3 — C — CH2 — OC 2H5 (B) CH3 — CH2 — C — OC 2H5
| |
CH3 CH3

(C) (D)

22. Neopentyl bromide is allowed to react with sodium ethoxide in ethanol. The major substitution product
formed in the reaction is -
CH3 CH3
(A) CH3 – C – CH2 – OC2H5 (B) CH3 – CH2 – C – OC2H5
CH3 CH3

CH3

(C) CH3 – CH – CHCH3 (D) (CH3)2CHCH2CH2 – OC2H5

OC2H5

23. (R)-2-Bromobutane is allowed to react with aqueous KOH. Identify the product formed in the reaction.

(A) (B)

(C) Equimolar amounts of (A) and (B) (D) Slight excess of (B)

24. The order of reactivity of the following halides towards hydrolysis by aqueous KOH is
(A) CH2 = CHCl < CH3CH2CH2Cl < CH2 = CH — CH2Cl
(B) CH2 = CHCl < CH2 = CHCH2Cl < CH3CH2CH2Cl
(C) CH2 = CHCH2Cl < CH2 = CHCl < CH3CH2CH2Cl
(D) CH3CH2CH2Cl < CH2 = CHCl < CH2 = CHCH2Cl

25. Ethylthioalcohol can be obtained when C 2H5Br reacts with -

(A) KSH (B) NaOH (C) K2S (D) Na2S
26. For CH3Br + OH– –––– CH3OH + Br –
the rate of reaction is given by the expression-
(A) rate = k [CH3Br] (B) rate = k [OH–]
(C) rate = k [CH3Br] [OH–] (D) rate = k [CH3Br]0 [OH–]0

27. (CH3)3CBr + OH– ––––– (CH3)3COH + Br –

Which of the following statements is true for the above reaction -
(A) If we double [RBr] the rate become four times
(B) If we reduce [OH]– to half, there is no change in the rate.
(C) If we double [RBr] the rate does not change.
(D) If we double [OH]– the rate double

28. Reactants of Strecker reaction are -

(A) ROH, PCl5 (B) RBr, Zn (C) RCl, Na2SO3 (D) ROH, HBr

29. The reaction of ethyl bromide with a lead-sodium alloy gives -

(A) Tetraethyl bromide (B) Tetraethyl lead (C) Sodium ethoxide (D) None of these

30. Treatment of ammonia with excess ethyl chloride will give -

(A) Diethylamine (B) Ethane (C) Methylamine (D) Tetraethyl ammonium chloride

31. In the reaction CH3CH2CHBrCH3 + (CH3)3COK – the main product is-

(A) (B)

(C) CH3CH2CH=CH2 (D) CH3CH=CHCH3

32. An alkyl halide reacted with a metal cyanide to give an alkanenitrile. The metal cyanide is
(A) AgCN (B) KCN (C) Cu2(CN)2 (D) Ba(CN)2

33. Which one of the following reaction is known as strecker;s reaction -

(A) R - X + NaI  R - I + NaX (B) R - X + Na2SO3  R - SO3Na + NaX
(C) RCOOAg + Br2  R - Br + AgBr + CO2 (D) None of the above

34. The reaction C2H5ONa + BrC2H5  C2H5–O–C2H5 + NaBr is called -

(A) Frankland reaction (B) Wurtz reaction
(C) Williamson’s synthesis (D) Cannizzaro reaction

35. Which chloride is the most reactive towards aqueous NaOH in -

(A) Methyl chloride (B) Chlorobenzene (C) Vinyl chloride (D) Benzyl chloride

36. Which of the following would be the strongest nucleophile in methanol-

(a) O H (b) S H (c) S eH (d) T eH
37. Predict the product in nucleophilic substitution reaction-

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

38. What is the major product of the given reaction-

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

39. Which of the following are the examples of strong nucleophiles but weak base in protic solvents?
(I) CH3S– (II) CH3O– (III) I– (IV) H2O (V) F–
(a) Both I and IV (b) Both IV and V (c) Both I and III (d) Both III and IV

40. The specific rotation of optically pure (R)-2butanol is –13.52º at 25ºC. An optically pure sample of (R)-2-
bromobutane was treated with aqueous NaOH in order to form 2-butanol via S N2 reaction. What would be the
specific rotation of the product assuming 100% yield-
(a) 0º (b) –13.52% (c) +13.52º (d) None of these

41. Which of the following correctly describe the relative nucleophilicities of methoxide and tertiary butoxide ion-
(a) These alkoxides have essentially the same nucleophilicities since, the negative charge in both is localised on an
oxygen atom
(b) Tertiary butoxide is more nucleophilic because it is more basic
(c) Methoxide is more nucleophilic because the nucleophilicity of tertiary butoxide is diminished by steric effect
(d) Tertiary butoxide is more nucleophilic because it contains three methyl groups which increases the charge on
oxygen by donating electron density

42. Arrange the following in increasing order of reactivity in an SN2 reaction with KI in acetone solvent.

(a) I < IV < III < II (b) IV < I < III < II (c) II < III < I < IV (d) III < II < I < IV

43. In the following set of nucleophiles, the strongest and the weakest nucleophile respectively are
(I) CH3S– (II) CH3COO– (III) HO– (IV) C6H5O–
(a) Both I and II (b) Both I and IV (c) Both III and II (d) Both IV and II
44. The major product of the following reaction is-
(a) (b) (c) (d)

45. Cyanide anion has two atoms that have lone pair of electrons. Either could act as nucleophile in the reaction. Yet in
the vast majority of the cases, carbon acts as nucleophile and forms a bond to the substrate , why?
(a) Nitrogen is strongely solvated in hydroxylic solvents, it will be less reactive
(b) Carbon is more reactive in polar aprotic solvents, normally used for these SN2 reactions
(c) Carbon atoms are more basic than nitrogen
(d) The lone pair of electrons on C is in sp hybrid orbital

46. In the following two phase reaction, catalyst works by

(a) Transforming CN– from the aqueous phase to organic containing C6H5CH2Br
(b) Transforming C6H5CH2Br from organic phase to the aqueous phase containing CN–
(c) Removing Br– from the organic base to aqueous phase
(d) Removing K+ from the organic phase to make CN– more nucleophilic

47. Which of the following would react most rapidly with sodium ethoxide to produce an ether?
(a) Chlorobenzene (b) 2-nitrotoluene
(c) p-nitrochlorobenzene (d) m-(chloromethyl)-toluene

48. In the given reaction, X will be-

(a) (b)
(c) 1 : 1 mixture of (a) and (b) (d) 2 : 1 mixture of (a) and (b)

49. In the given reaction, X will be-

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

50. Consider the following reaction,

What can be correctly predictied regarding this reaction-

(a) SN1 reaction is occuring
(b) SN2 reaction is occurring
(c) Neighbouring group participation and SN2 reaction are occurring
(d) Neighbouring group participation and SN1 reaction are occurring
51. For the following reaction, pick out the best term which describe its mechanism-

(a) SN1 (b) SN2

(c) SN2 with neighbouring group participation (d) Addition followed by substitution

52. The most reactive in the following in reaction with NaCN is-

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

53. Which SN2 reaction would take place most rapidly-

(a) (b)

(c) (d)

54. The reactivity of 2-bromo-2-methyl butane (I), 1-bromo pentane (II) and 2-bromo pentane (III) towards SN2
reaction is-
(a) I > II > III (b) I > III > II (c) II > III > I (d) II > I > III

55. Which of the following is correct increasing rate of SN2 reaction?

(a) II < III < I < IV (b) IV < III < II < I (c) III < II < IV < I (d) I < IV < II < III

56. Chloroethane is treated separately with aqueous NaSCN and NaOCN. Which of the following is true statement
regarding the substitution product-
(a) In both case, C – N bond is mainly formed
(b) In no case, the major product involves formation of C – N bond
(c) With NaSCN, mainly C – S bond is formed while with NaOCN, mainly C – N bond is formed
(d) With NaSCN, mainly C – N bond is formed while with, mainly C – O bond is formed

57. The major product in the following reaction is-

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

58. Chlorine is the most reactive towards aqueous NaOH in :

(a) methyl chloride (b) chlorobenzene (c) vinyl chloride (d) benzyl chloride
59. What will be the major monobromination product in the following reaction-

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

60. Predict substitution product in the following reaction-

(a) (b) (c) Both (a) and (b) (d) None of these

61. Propose product with appropriate stereochemistry in the following SN2 reaction-

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

62. The major product in the reaction is :

(a) (CH3)2C = C (CH3)CH2CH3 (b)

(c) (d)

63. Choose the incorrect statement:

(a) an S N 1 reaction proceeds with inversion of configuration
(b) an S N 2 reaction proceeds with stereochemical inversion
(c) an S N 2 reaction follows second-order kinetics
(d) the reaction of tert. butyl bromide with OH follows first-order kinetics.

64. Arrange H2O, O-H, CH3O- and CH3COO- in descending order of nucleophilicity (rate of reactivity).
(a) H2O > O-H > O-CH3 > CH3COO- (b) O-CH3 > O-H > CH3COO- > H2O
(c) O-H > O-CH3 > H2O > CH3COO- (d) CH3COO- > O-CH3 > O-H > H2O
65. Which of the following is an S N 2 reaction ?
(a) (CH3)3CBr + KOH  (CH3)3COH + KBr
(b) CH3CH2Br + CH3CH2ONa  CH3CH2OCH2CH3 + NaBr

(c)

(d) All of the above

66. In S N 2 reactions, the order of reactivity of the halides CH3X, C2H5X, n-C3H7X, n-C4H9X is :
(a) CH3X > C2H5X > n-C3H7X > n-C4H9X (b) C2H5X > n-C3H7X > n-C4H9X > CH3X
(c) C2H5X > n-C3H7X n-C4H9X > CH3X (d) n-C4H9X n-C3H7X > C2H5X > CH3X

 
OH
67.  OH
 Steps I and II are
II I

B A
(A) I can't be SN1 (B) II can't be SN1 (C) I SN1 & II SN2 (D) I SN2 & II SN1

68. NaOH
 A. A is:
excess

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

69. The major product in the given reaction: + NH3 

(A) (B) (C) (D) All of these

CH  C CNa
70. In the given reaction: 3  the products are:
Et 2O / 

(A) and (B) +

(C) (D)

71. Which of the following nucleophile will show minimum reactivity towards SN2 reaction:
  
(A) Me 3 C O  (B) MeO  (C) (D) Me 2CHO 
72. In the given reaction  [X]
NaOH
25 C

(A) (B) (C) Mixture of (A) and (B) (D)

(i ) NaN
73. In the given reaction:  3  [X] [X] will be:
(ii ) HOH

(A) (B) (C) Mixture of (A) and (B) (D)

S 2
74. + OH– 
 A
N A is:

(A) (B)

(C) Both (D) None

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

76. Non-occurence of the following reaction Br– + CH3OH  BrCH3 + OH–, is due to
(A) Attacking nucleophile is stronger one (B) Leaving group is a strong base
(C) Alcohols are not good substrate (D) Hydroxide ions are weak bases

77. The reactivity of 2-bromo-2-methylbutane (I), 1-bromopentane (II) and 2bromopentane (III) towards S N2
displacement is such that:
(A) I > II > III (B) I > III > II (C) II > III > I (D) II > I > III

78. Which reaction proceeds faster with NaI in DMSO.

CH2Cl Cl CH2Cl
Cl
(A) CH3 (B) (C) (D)

H
79. The product P of the following reaction is KCN
 Product (P) Major
CH2OTs Ethanol H 2O

CN

(A) (B) (C) CH2CN (D)

 ?
80. Which reaction conditions is suitable for the following reaction: 


(A) Br2 / CCl4 (B) SOBr2 (C) HBr /conc H2SO4 (D) PBr3

81. Arrange these compounds in order of increasing SN2 reaction rate:

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

82. Benzoyl chloride is less reactive than acetyl chloride for nucleophilic acyl substitution reaction because
O
||
(A)  C  group of benzoyl chloride is in conjugation with benzene ring. This makes benzoyl chloride more
stable than acetylchloride.
(B) CH3– group of acetyl chloride make C–Cl bond stronger due to the +I effect.
(C) C6H5– group of benzoyl chloride make C–Cl bond weaker due to +R effect.
(D) Carbonyl carbon in benzoyl chloride is less electron deficient than acetyl chloride

83. From each of the following pairs select the compound that will react faster with sodium iodide in acetone.
(a) 2-Chloropropane or 2-bromopropane
I II
(b) 1-Bromobutane or 2-bromobutane
I II
(A) (a)-I, (b)-I (B) (a)-I, (b)-II (C) (a)-II, (b)-I (D) (a)-II, (b)-II

PhCO H  PI , 
H 3O
84. CH2 = CH2  
3
 A   B 3 C Structure of C is
( 2 eq )

(A) CH 2  CH 2 (B) CH2=CH2 (C) (D) CH 2  CH 2

| | | |
OH I I I

85. (I) aq

.KOH

 X (II) aq
.KOH

 Y

Select true statement for above reaction:

(A) Reaction I & II follow same mechanism. (B) Reaction I & II follow different mechanism.
(C) X & Y are same compound (D) X & Y are different compounds,

Multiple Correct
86. In a SN2 reaction rate of reaction depends on-
(a) Concentration of substrate (b) Concentration of nucleophile
(c) Nature of leaving group (d) Number of lone pairs on donor atom
87. Consider the reaction given below :

The correct statement(s) applicable to the above reaction is/are-

(a) Cl– is substituted predominantly
(b) Cl– is a better leaving group
(c) Substitution of I– in the above reaction required greater activation energy than for Cl–
(d) Addition of some NaI catalyst the substitution reaction

88. A SN2 reaction involves back side attack of nucleophile at the a-carbon of substrate because-
(a) Both nucleophile and leaving group are electron rich, nucleophilic attack occur from most distant position
(b) There is greater electron density on the back side of substrate
(c) There is not enough physical space in the front side from where leaving group leaves the substrate
(d) Substrate possesses a hole in the backside

89. 1-chlorobutane is more reactive than 2-chloro-2-methyl propane in a SN2 reaction because-
(a) -carbon is less crowded in 1-chlorobutane
(b) -carbon is less electropositive in 1-chlorobutane
(c) Electron donating inductive effect of three methyl group is greater in 2-chloro 2-methyl propane
(d) -carbon is more electropositive in 1-chlorobutane

90. In which of the following pair(s), the first one is stronger nucleophile than the second one-
(a) CH3O–, (CH3)3CO– (b) (CH3)2N–, NH2–
(c) C6H5O–, (CH3)2CHO– (d) HS–, HO–

91. In which of the following pair(s), the first one is better leaving group than the second one-
(a) Br–, I– (b) I–, CF3SO3–
(c) CF3SO3–, CH3SO3– (d) p-O2N-C6H4-SO3–, C6H5SO3–

92. In which of the following reaction, inversion of configuration at chiral carbon takes place-

(a) (b)

(c) (d)

93. Consider the following SN2 reaction, 1-bromobutane + NaCN(aq)  pentanenitrile + NaBr
Which of the following solvent(s) when replaces water in the above reaction, increases the rate-
(a) Acetone (b) Dimethyl sulphoxide
(c) N,N-dimethyl formamide (d) Tetrahydrofurane

94. Which of the following is/are ambident nucleophile-

(a) CN– (b) OCN– (c) SCN– (d) NO2–
95. Pick out the alkyl bromides which proceeds with retention of configuration in an SN2 reaction with CH3ONa(aq)

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

96. Consider the following substitution reaction,

The correct statement(s) is/are-

(a) Reaction occur at much faster rate than when substrate is 2-bromo-3,3-dimethyl pentane
(b) Reaction occur with inversion of configuration
(c) Reaction occur with retention of configuration
(d) E2 product is preferred over SN2

97. Select the correct statement -

(a) 1-iodopropane reacts more rapidly than 2-iodo propane in SN2 reaction
(b) 1-chloropropane has greater reactivity than 1-bromopropane in SN2 reaction
(c) 1-bromopropane reacts faster than (CH3)3CCH2Br under SN2 condition
(d) p-CH3O – C6H4 – Br has greater reactivity than p-O2N – C6H4 – CH2Br in SN2 reaction

98. Consider the following SN2 reaction,

The correct statement is(are)-

(a) Addition of (C4H9)4NCl catalyst reaction
(b) Reaction occur smoothly even in the absence of any catalyst
(c) Labeling a-14C will increase the rate of reaction
(d) Substitution KCN by AgCN (saturated) will yield isocyanide as the major product

99. 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

100. In which of the following case configuration about chiral C* is retained:

CH Br SOCl CH ONa
(A) Na
 3 (B) 2  3


(C) 
PCl
3  3
CH ONa
(D) H/
MeOH



101. Which of the following will react with AcOAg

(A) R–NH2 (B) R–OTs (C) R–N3 (D) R–Br
 CH 3
|
H  C  OTs NaCN
 CH 3CH 2 CH  CN
102. Consider the given reaction` |
C 2 H 5 (S) |
CH 3
which of following statements are correct for above reaction.
(A) Product formation takes place due to the breaking of O–Ts
(B) The reaction is S 2
N
(C) The reaction is S
N1
(D) Configuration of product is (R)

103. SN2 reaction will be negligible in

Br

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

104. Rate of SN2 depends on

(A) Conc of Nucleophile (B) Conc of substrate
(C) Nature of leaving group (D) Nature of solvent

105. In the given pair in which pair the first compound is more reactive than second to SN2 reaction.

Cl
(A) Cl CH2Cl (B)
Cl

Cl Cl

(C) (D)
Cl Cl
 ANSWER KEY
1. A 2. D 3. D 4. C 5. D 6. D 7. B 8. A
9. A 10. C 11. C 12. D 13. D 14. B 15. C 16. C
17. D 18. C 19. B 20. C 21. C 22. A 23. A 24. A
25. A 26. C 27. B 28. C 29. B 30. D 31. C 32. B
33. B 34. C 35. D 36. D 37. D 38. B 39. C 40. C
41. C 42. B 43. B 44. C 45. C 46. A 47. D 48. C
49. C 50. C 51. C 52. D 53. A 54. C 55. C 56. C
57. C 58. D 59. C 60. B 61. D 62. A 63. A 64. B
65. B 66. A 67. C 68. B 69. A 70. B 71. A 72. D
73. C 74. B 75. C 76. B 77. C 78. B 79. C 80. D
81. A 82. D 83. C 84. B 85. B
86. ABC 87. ACD 88. AC 89. ACD 90. AD 91. CD
92. AD 93. ABCD 94. ABCD 95. ABC 96. AC 97. AC
98. AD 99. AC 100. AC 101. BCD 102. BD 103. ABC
104. ABCD 105. BD