SRI VIJAY VIDYALAYA COLLEGE OF ARTS & SCIENCE,

NALLAMPALLI
Accredited with ‘A’ grade by NAAC
M.Sc. ORGANIC CHEMISTRY –I
UNIT III
ALIPHATIC NUCLEOPHILIC SUBTITUTION REACTION
1. Nucleophiles are

a) lewis acids b) lewis bases c) catalyst d)proton donor

2. Which of the following is not a nucleophile?

a) OH- b)NH3 c) BF3 d) HSO3-

3. Neutral nucleophile forms the following?

a) DMSO b) NH2- c) NH3 d) all of these

4. Which is strong nucleopille among the following?

a) OR- b) NH2 c)CH3COO- d)OH-

5. The reaction of C2H5Br+NaOH→C2H5OH+NaBr is -

a) Nucleophilic b) Electophilic c) redox d) free radical rxn

6. In SN1 reaction mechanism the rateof reaction depends on concentration of

a) Substrate only b) nuclophile only c) both substrate and nucleophile d) solvent

7. Nucleopilic strengthis not important in

a)SN1 b) SN2 c) SNi d) all

8. Which of the following is an ambident nucleophile ?

a) ethoxide ion b) cyanide ion c) acetate ion d) ammonia

9. Which of the following is an ambident nucleophile ?

a) CH≡C- b) CH2=CH- c) CH3CH2 d)none of these

10. The neutral nuclphiles ( non – bonding lone pairs ) from following is

a) H2O b) NH3 c) (CH3)2S d) all of these

11. Which one of the following is more reactive alkyl halide towards nuclephilic
reactions?

a) CH3F b) CH3I c) CH3Br d) CH3Cl

12. Which of the following alkyl halide is undergoing solvolysis by SN1 reaction?

a) CH3-Cl b) CH3- CH2- Cl c) CH3-CH2 –CH2-Cl d) (CH3)3 C-Cl

13. In theSN2 reaction the more reactive among the following?

a) C6H6 b) CH3CH2-Br c) CH3 –Br d)( CH3)3C-Br

14. The rate limiting step for the hydrolysis t- butyl butanol involves the formation of

a) Carbanion b) a Carbocation c) Free radical d) Single transition state

15. Which one of the following is most effective in SN2 reaction?

a) C2H5O- b) OH - c) C6H5O- d) CH3COO-

16. The carbonium ion obtained in SN1 reaction is

a) Square planar b) linear c) Tetrahedrl d) Planar

17. The intermediate obtained during the SN2 reaction

a) Trigonal bipyramidal b) Trigonal planar c) linear d) Tetrahedran

18. In SN2 reaction mechanism the coordination number of carbon in transition state is

a) 3 b) 4 c) 5 d) 6

19. Retention of configurationis observed in

a) SN1 b) SN2 c) SNi d) all of these

20. Arrange the following in the order of increasing basicity H2O,OH-.,C2H5OH,CH3O-

a) OCH3>OH−>C2H5OH>H2O b) -OH>-OCH3> 𝐻2O> C2H5OH

c) H2O>C2H5OH >OH- >O-CH3 d) - OCH3>H2O>C2H5OH>OH

21. Which is more reactive chlorides for SN2 reaction

(a) C2H5Cl (b) CH2=CH-Cl (c) C6H5-Cl (d) (CH3)2CH-CH2-Cl
22. In SN1 reaction which of the following is more reactive halide
(a) Cholorobenzene (b) Isopropylchloride (c) T-butyl chloride (d) Ethyl chloride

23. Choose the correct order of basic strength of the following

(a) CH3-CH2>CH2=CH >CH==C (c) CH2=CH2>CH=C >CH3CH2
(b) CH=C>CH2=CH >CH3CH2 (d) CH3CH2>CH=C >CH2==CH

24. In SN2 reaction nucleophilic cannot attack front side of carbon because
(a) Substrate is SP3 carbon and TD (b) Steric hindrance (c) Both a & b (d) None of these

25. Which of the following is not an ambident nucleophile

(a) CN (b) S-CN (c) No2 (d) NH3

26. DMSO is example for

(a) Ambident nucleophile (b) Neutral nucleophile (c) Negative Nucleophile (d) Electrophile

27. The nucleophiles which have more than one suitable atom through which they can attack the
substrate is called
(a) Neutral nucleophile (b) ambident nucleophile (c) Negative Nucleophile (d) None of these

28. Which one of the following cannot undergo nucleophile substitution under ordinary
condition?
(a) Ethyl chloride (b) Benzyl chloride (c) N-propyl chloride (d) Vinyl chloride

29. The increasing order of leaving groups from the following is

(a) l>Br>Cl>F (b) F>Br>Cl>l (c) F>Cl>Br>l (d) Br>Cl>F>l

30. Which is the neutral nuclcophile among the following?

(a) OR (b) OH (c) (CH3)2S (d) RS

31. Order of hydrolysis of the following in increasing order is

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

32. The most reactive alkyl halide for the SN2 reaction is
(a) CH3-Cl (b) CH3CH2-Cl (c) (CH3)2CH-Cl (d) (CH3)3C-Cl

33. Which of the following will not act as neighboring group participation?
(a) OR (b) NH2 (c) NO2 (d) None of these

34. The incorrect statement that vinyl chloride does not react with a base in a SN2 reaction is
 (a) OH-is a weak nucleophile (b) The SP2-C-Cl bond is stronger than SP3-C-Cl bond
(c) Steric hindreance at carbon bearing Cl (d) none of the correct

35. In the formation of (CH3)3C-O-CH3 by SN2 reaction, the substrate would be

(a) (CH3)3C-Br (b) (CH3)3C_OCH2Cl (c) CH3Br (d) CH3OH

36. Aryl and vinyl halides are less reactive towards SN reactions as compard to alkyl halides due
to
(a) Formation of more stable carbocation (b) Resonance stabilization
(c) Long- carbon halogen bond (d) Cannot be predict

37. Order of the following molecule with respect to their reactivity

(a) 2>3>1 (b) 1>3>2 (c) 3>2>1 (d) None of above

38. Which is the suitable solvent for SN1 reaction?

(a) NH3 (b) CH3OH (c) H2o (d) All of these

39. In this reaction, the product is

(a) Possible by SN1 (b) not possible by SN1 and SN2
(b) (c) Possible by SN1 (d) Both SN1 and SN2 is possible

40. Optically active alkyl halides undergo solvolysis gives

(a) Inversion product (b) Recemie mixture (c) both inversion and retention (d) No product

41. Cyclohexyl bromide undergo solvolysis will give the most stable product which in a

42. Benzyl chloride undergo nucleophilic substitution will give the product benzyl alcohol by
(a) SN1 (b) SN2 (c) Both SN1 and SN2 (d) None of these

43. SN2 reaction takes place with

(a) Inversion of configuration (b) Retention (c) Racemisation (d) None of these

44. Which of the following substratr will be least reaction to SN1 reaction?

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

45. Which one of following primary alkyl bromides gives nucleophilic substitution by SN1
mechanism?
(a) (CH3)3C-CH2-Br (b) CH3-CH2-Br (c) CH3-Br (d)CH3-CH2-CH2-Br

46. Which of the following alkyl halides would be the most reactive in a SN2 reaction?
(a) C6H5CH2CH2CH2Br (b) C6H5CH(CH3)CH2Br
(c) C6H5C(CH3)2Br (d) C6H5CH2CH(Br)CH3

47. What is the best reagent to convert isopropyl alcohol to isopropyl bromide?
(a) HBr (b) SOBr2 (c)Br2 (d) CH3MgBr

48. Which of the following compounds would undergo solvolysis most rapidly in aqueous
ethanol?

49. In the reaction if the concentration of both the reactants is

doubled then the rate of reaction will be.
(a) Remain unchanged (b) Double (c) Reduced to one fourth (d) Quadruple

50. Increasing the concentration of nucleophile in SN2 reaction the rate of the reaction is-
(a) Increased (b) Decreased (c) No change (d) Not determined

51. Walden inversion is takes place in

(a) SN1 (b) SN2 (c) SNi (d) In all

52. Which is the most effective is increasing the rate of reaction of aliphatic nucleophilic
substitution
(a) Nucleophile (b) Substrate (c) Solvent (d) Neighbouring group participation

53. Which is not act as a neighbouring group nucleophile from the following
(a) NH2 (b) OH (c) OCH3 (d) None of these

54.

(a) H2O (b) NH3 (c) NaNH2 (d) NH2-NH2

55. Which of the following pairs of compound has a faster rate of SN1 reaction?

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

56. Which of the following alkyl halides is most reaction towards SN1 and SN2 displacement?
(a) R-Br (b) R-Cl (c) R-F (d) R-l

57. Conversion of C2H5Cl into C2H5OH is

(a) SN2 mechanism (b) E2-mechanism (c) El-mechanism (d) SNL mechanism

58. SNi mechanism leads to

(a) Inversion (b) Retention (c) Recemisation (d) meso

59. The rate of hydrolysis of the following compounds by SN1 follows

(a) 1>2>3>4 (b) 2>3>4>1 (c) 4>3>2>1 (d) 3>2>4>1

60.The Intermediate obtained during the SN2 reaction is

(a) Trigonal planner (b ) Trigonal bipyramidal

(a) Linear (d) Tetrahedral

61.The Claisen Condensation is used in the preparation of

(𝑎)𝛿-Keto ester (b) γ- keto ester (c) β-keto ester (d) β-Hydroxyl ester

62.In which of the following reaction same (or) different ester to β- keto ester which is used as
a base catalyst?

(a)Lossen Rearrangement (b) Claisen Condensation

(c)Claisen Rearrangement (d) Dieclemann Condensation

63.The reagent used in Claisen Condensation is

(a) NaNH2/NaH (b) Hcl, sncl2 (c) Zn/ Hcl (d) Koc(CH3)3

64.The product of the following Claisen Condensation reaction is Ethyl acetate + Methyl
acetateNaNH2?

(a) Ethyl aceto acetate (b) β-Keto ester (c) Methyl acetate (d) Methyl aceto acetate

65. CH3-C-OC2H5 C2H5ONa A is formal by Claisen Condensation the correct statement

about A is

I. A Formas Oxime II. A shows tautomerism III. A shows Iodoform test

(a) I, III (b) I, II, III (c) I, II (d) Only III

66.Consider the following statements

 I. Claisen rearrangement is a (2,2) sigmatropic rearrangement

II. Claisen rearrangement proceeds via cyclic transition state

III. Claisen rearrangement is concerted Inteamolecula rearrangement

(a) I,II (b) I,III (c) II,III (d) Only I

67.In an ester involves Claisen Condensation it contains

(a) 𝛾-Hydrogen (b) α-Hydrogen (c) β-Hydrogen (d) 𝛿-Hydrogen

68.Product of the following reaction is

69.The base is used in the Claisen Condensation _________

(a) Sodium alkoxide (b) Metallic Na (c) NaNH2 (d) All of these

.70.Find out the following reaction.

71.Dieckmann condensation is used in the preparation of

(a) β-Keto ester (b) Cycllic Ketones (c) Ketones (d) Aldehydes

72.In which of the following reaction dieters into Cyclic Ketones are?

(a) Claisen Condensation (b) Dieckmann rearrangement

(b) Dieckmann Condensation (d) Claisen rearrangement

73.The reagent is used in the Dieckmann Condensation is

(a) NaNH2 / NaH (b) Hcl,sncl2 (c) Zn / Hcl (d) Na/NaoEt

74.

This transformation is an example of

(a) Stobbe Condensation (b) Darzen Condensation

(c) Dieckmann Condensation (d) Claisen Condensation

75.

76.The diester of dibasic acids is a reactant for Dieckmann Condensation it yields.

(a) β –Keto ester (b) Cyclic Ketones (c) α-Keto ester (d) δ-Keto ester

77.Dieckmann Condensation is called as

(b) Intramolecular Claisen Condensation (c) Intermolecular Claisen Condensation

(c) Intramolecular Dieckmann Condensation (d) Intermolecular Dieckmann

Condensation

78.The Intermediate of following reaction is

(b) 2-Carboethoxy Cyclopentanone (b ) Cyclopentanone

(d) Cyclopentanone (d) Ethyl ester of adipic acid

79.The name of the following reaction is

(a) Claisen Condensation (b) Darzen Condensation

(c) Stobbe Condensation (d) Dieckmann Condensation

80. Benzyl chloride undergo nucleophilic substation will give the product benzyl alcohol by

(a) SN1 (b) SN2 (C) Both SN1 & SN2 (d) None of these
UNIT – III ANWER KEY ( I- PG ORGANIC –I)

1 B 21 A 41 C 61 C
2 C 22 C 42 B 62 B
3 C 23 A 43 A 63 A
4 B 24 A 44 A 64 A
5 A 25 D 45 A 65 B
6 A 26 B 46 A 66 C
7 A 27 B 47 B 67 B
8 B 28 D 48 A 68 B
9 C 29 A 49 A &B 69 D
10 D 30 C 50 A 70 C
11 D 31 D 51 B 71 B
12 D 32 A 52 D 72 C
13 C 33 C 53 C 73 D
14 B 34 A 54 A 74 C
15 A 35 C 55 B 75 C
16 D 36 B 56 A 76 A
17 A 37 C 57 D 77 A
18 C 38 D 58 A 78 A
19 C 39 B 59 B 79 D
20 A 40 B 60 B 80 A