REACTION INTERMIDIATES & ELECTRONIC DISPLACEMENTS

Q 1. The stability of a carbonium ion depends upon:

(a) the bond angle of the attached group
(b) the substrate with which it reacts
(c) the inductive effect and hyper-conjugative effect of the attached group
(d) none of the above

Q 2. Which of the following statements is correct?

(a) Allyl carbonium ion (CH2 = CH - +CH2) is more stable than propyl carbonium ion
(b) Propyl carbonium ion is more stable than the allyl carbonium ion
(c) Both are equally stable
(d) None of the above

Q 3. Which one of the following orders is correct regarding the -I effect of the substituents
(a) – NR2 < – OR > – F (a) – NR2 > – OR > – F
(c) – NR2 < – OR > – F (d) – NR2 > – OR < – F

Q 4. Delocalised electrons are present in:

(a) 1, 3-butadiene (b) C6H6 (c) 1, 3, 5-hexatriene (d) All of these

Q 5. Resonance energy is more for :

LS
(a) C6H6 (b) cyclohexene (c) cyclohexadiene (d) cyclohexatriene

IA
Q 6. Cummulated diene among the following is:
(a) CH2 = CH — CH = CH2 (b) CH2 = C = CH2
R
(c) benzene (d) both (a) and (c)
TO

Q 7. What is the decreasing order of strength of the bases?

NH 2 , HX  C  and CH3CH 2
U

(a) CH3CH2  NH2  HC  C  (b) HC  C   CH3CH 2  NH 2

T

(c) NH 2  HC  C   CH3CH 2 (d) NH 2  CH3CH 2  HC  C 

JI

Q 8. The stability of the carbocation decreases in the order :

LA

(a) R2 CH+ > R3C+ > RCH 2 > CH 3 (b) R3 C+ > R2CH+ > RCH 2 > CH 3
(c) CH 3 > R2CH+ > RCH 2 > R3 C+ (d) CH 3 > RCH 2 > R2CH+ > R3 C+
A
B

Q 9. Correct order of nucleophilicity is :

(a) CH3  NH 2  OH   F  (b) F   OH   CH3  NH 2
(c) OH   NH 2  F   CH3 (d) F   OH   NH 2  CH3

Q 10. More stable carbocation is formed during the heating of which one of the following compound with
conc. H2SO4 :
(a) (CH3)3COH (b) C6H5CH2OH (c) (CH3)2 CHOH (d) CH3CH(OH)CH2CH3

Q 11. One of the resonating forms of methyl vinyl ketone is :

(a) (b)

(c) (d)

Q 12. The order of stability of the following carbanion is:

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 (i) (b) (c) (d)

(a) I > II > IV (b) I > III > H > IV (c) IV > III > II > I (d) III > IV > I > II

Q 13. The most stable carbocation is

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

Q 14. Arrange the following free radicals in order of stability :

benzyl allyl allyl methyl vinyl
I II III IV

LS
(a) IV > III > II > I (b) I > II > III > IV
(c) II > IV > III > I (d) III > II > I > IV

IA
R
Q 15. The order of stability of the alkenes :
R2C = CR2, R2C = CHR, R2C = CH2,
TO

I II III
RCH = CHR, RCH = CH2
U

IV V
(a) I > II > III > IV > V (b) I = II > III > IV > V
T

(b) II > I > IV > III > V (d) V > IV > III > I > II
JI

Q 16. The stability of the free radicals allyl, benzyl, 3, 2, 1 and CH3 is in the order :
LA

(a) benzyl > allyl >3 > 2° > 1° > CH3 (b) allyl > benzyl > 3° > 2° > 1 > CH3
(c) 3° > 2° > 1 > CH3 > allyl > benzyl (d) 3° > 2 > 1 > CH3 > allyl = benzyl
A

Q 17. The basic strength of CH  C, CH 2  CH , CH3CH 2 will be in order:

B

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

Q 18. Consider the following carbanions :

correct order of stability is :

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

Q 19. Stability of which intermediate is not govern by hyperconjugation?

(a) Carbon cation (b) Carbon anion
(c) Carbon free radical (d) None of these

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Q 20. Hyperconjugation is :
(a) - delocalisation (b) no bond resonance
(c) - conjugation (d) all of these

Q 21. Correct order of nucleophilicity is :

(a) I- > Br- > Cl- > F- (b) F- > Cl- > Br- > I- (c) Cl- > F- > Br- > I- (d) I- > Cl- > Br- > F-

Q 22. Correct gradation of basic character :

(a) NH3 > CH3NH2 > NF3 (b) CH3NH2 > NH3 > NF3
(c) NF3 > CH3NH2 > NH3 (d) CH3NH2 > NF3 > NH3

a b b c d e f
Q 23. Different hydrogens in C H 3 C H  C H  C H 2  C H 2  C H (C H 3 )2 are represented by alphabests.
Arrange them in decreasing order of reactivity towards radical substitution :
(a) C > A > e > d > f > b (b) f > b > a > c > d > e
(c) b > c > a > f > d > e (d) a > b > c > d > e > f

Q 24. Heterolysis of CH3CH2CH3 results in formation of :

LS
(a) (b) C H 3 and C 2 H 5 (c) (d) CH 3 and C2 H 5

Q 25. Correct order of basisity of P S and I ethyl amine is:

IA
R
(a) P > S > T (b) T > S > P (c) S > P > T (d) S > T > P
TO

Q 26. The inductive effect :

(a) implies the atom’s ability to cause bond polarization
U

(b) increases with increase of distance

(c) implies the transfer of lone pair of electrons from more electronegative atom to the lesser
T

electonegative atom in a molecule

JI

(d) implies the transfer of lone pair of electrons from lesser electronegative atom to the more
electronegative atom in a molecule
LA

Q 27. Which of the following belongs to + I group?

(a) —OH (b) — OCH3 (c) —COOH (d) —CH3
A
B

Q 28. The oxygen atom in phenol:

(a) exhibits only inductive effect
(b) exhibits only resonance effect
(c) has more dominating resonance effect than inductive effect
(d) has more dominating inductive effect than the resonance effect

Q 34. In which of the following molecules, the resonance effect is not present ?

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

Q 35. Which of the following is not a nucleophile?

(a) BF3 (b) CO2 (c) H2O (d) NH3

Q 36. Which of the following is an electrophile ?

(a) : CCl2 (b) CO2 (c) H2O (d) NH3

Q 37. The pKa values of four acids are given below. Which one will correspond to the weakest acid ?
(a) -1.3 (b) 4.72 (c) 9.2 (d) 16.0

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Q 38. Which of the following orders of relative strength of acids is correct ?
(a) CH3COOH > HCN > H2O > C2H5OH (b) CH3COOH < HCN < H2O < C2H5OH
(c) CH3COOH > HCN > H2O > C2H5OH (d) CH3COOH < HCN < H2O > C2H5OH

Q 39. Which of the following orders of relative strength of bases is correct ?

(a) CH3COO- > CN- > OH- > C2H5O- (b) CH3COO- < CN- > OH- < C2H5O-
- - - -
(c) CH3COO > CN < OH > C2H5O (d) CH3COO- < CN- < OH- > C2H5O-

Q 40. Which of the following is the most stable carbocation ?

   
(a) C H 3 (b) R C H 2 (c) R 2 C H (d) R 3 C

Q 41. Which of the following orders is true regarding the acidic nature of COOH ?
(a) Formic acid > acetic acid > propanoic acid
(b) Formic acid > acetic acid < propanoic acid
(c) Formic acid < acetic acid > propanoic acid
(d) Formic acid < acetic acid c propanoic acid

Q 42. An electrophilic reagent must have:

LS
(a) a vacant orbital
(b) an orbital containing one electron

IA
(c) an orbital containing two electrons
(d) all completely filled atomic orbitals
R
Q 43. Which of the following is an electrophile?
TO

(a) Na+ (b) Li+ (c) H+ (d) Ca2+

U

Q 44. Which of the following orders is correct regarding the basicity of NH2 group?
(a) CH3NH2 > (CH3)2 NH > (CH3)3N (b) CH3NH2 > (CH3)2 NH < (CH3)3N
T

(c) CH3NH2 > (CH3)2 NH < (CH3)3N (d) CH3NH2 < (CH3)2 NH > (CH3)3N
JI

Q 45. Which of the following orders is correct regarding the acidity of carboxylic group?
LA

(a) CH3CH2CH (Cl)COOH > CH3CH(Cl)CH2COOH > ClCH2CH2CH2COOH

(b) CH3CH2CH (Cl)COOH < CH3CH(Cl)CH2COOH < ClCH2CH2CH2COOH
A

(c) CH3CH2CH (Cl)COOH > CH3CH(Cl)CH2COOH < ClCH2CH2CH2COOH

(d) CH3CH2CH (Cl)COOH < CH3CH(Cl)CH2COOH > ClCH2CH2CH2COOH
B

Q 46. Which of the following is the most stable radical?

(a) CH 3 (b) R CH 2 (c) R2 CH  (d) R3C 

Q 47. Which of the following statements is correct ?

(a) +I group stabilises a carbocation (b) + I group stabilises a carbanion
(c) – I group stabilises a carbocation (d) – I group destabiises a carbanion

Q 48. Which of the following orders is correct regarding the –I effect of the substituents?
(a) – NR2 > – OR > – F (b) – NR2 < – OR < – F
(c) – NR2 > – OR < – F (d) – NH2 < – OR > – F

Q 49. Which of the following orders is not correct regarding the - I effect of the substituents?
 
(a) –I < –Cl < –Br < – F (b)  N R3   O R2
 
(c)  N R2  OR   F (d)  SR  OR   O R2

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Q 50. Which of the following orders is correct regarding the acidity of carboxylic acid ?
(a) Cl3CCOOH > Cl2CHCOOH > ClCH2COOH
(b) Cl3CCOOH > Cl2CHCOOH < ClCH2COOH
(c) Cl3CCOOH < Cl2CHCOOH > ClCH2COOH
(d) Cl3CCOOH < Cl2CHCOOH < ClCH2COOH

Q 51. The reaction  CH 3 3 C  Br H 2O

  CH 3 3 COH is :
(a) elimination (b) substitution (c) free radical (d) addition

Q 52. The reaction C2 H5 I  KOH  C2 H5OH  KI is called :

(a) hydroxylation substitution (b) electrophilic substitution
(c) nucleophilic substitution (d) dehydroiodination

Q 53. Which of the following is protic solvent ?

(a) HCOOH (b) CH3CN (c) C2H5O-Na+ (d)

Q 54. Consider the following reaction :

> C = O + H2NOH  >C = NOH + H2O is an example of :

LS
(a) substitution (b) elimination (c) addition (d) addition elimination

Q 55. The chlorination of methane to give CCl4 is an example of:

(a) addition (b) elimination (c) substitution IA (d) chain reaction
R
TO

Q 57. Examine the following statements regarding S N 2 reaction :

(1) The rate of reaction is independent of concentration of nucleophile
U

(2) The nucleophile attacks the carbon atom on the side of molecule opposite to the group being
displaced
T

(3) The reaction proceeds with simultaneous bond formation and rupture
JI

Which of the above written statements is correct:

(a) 1, 2 (b) 1, 3 (c) 1, 2, 3 (d) 2, 3
LA

Q 58. Which of the following is an example of S N 2 reaction :

A
B

(a) CH3Br + O-H  CH3OH + Br- (b)

(c) (d) none of the above

Q 59. Order of reactivity of R-X having same alkyl group but different halogens in S N 2 machanism is:
(a) RF > RCl > RBr >RI (b) RF > RBr > RCl > RI
(c) RI > RBr > RCl >RF (d) RI > RCl > RBr > RF

Q 60. Which is wrong about S N1 mechanism ?

(a) Partial inversion and partial retention takes place
(b) Polar solvent favours S N1
(c) Stronger nucleophile favours the rate of reaction
(d) More stable carbonium ion favours

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Q 61. Which is wrong about S N 2 :
(a) Bulkier alkyl group hinders S N 2
(b) Non-polar solvent favours S N 2
(c) Inversion takes place
(d) Stronger nucleophile retards S N 2 reaction

Q 67. Which of the following reaction proceeds through S N 2 mechanism :

(a) CH 3CH 2CH 2 Br  CH 3O  
50 C
CH 3OH
(b) CH 3CH 2CH 2 Br   CH 3 3 CO  
 CH3  COH
50 C

3

(c)  CH 3CH 2 3 CBr  OH 

 50 C
CH 3OH
(d) all of the above

Q 68. The reaction: is described as :

(a) SE2 (b) S N 2 (c) S N1 (d) S N0

LS
Q 69. Which of the following can show S N 2 reaction:

(a) (b) IA
R
TO

(c) (d) None of the above

T U

Q 75. Which of the following types of reaction occurs when a substituent has got a double bond with
JI

evenly distributed  electron cloud ?

LA

(a) Electrophilic addition (b) Nucleophilic addition

(c) Any of the 2 written above (d) None of the above
A

Q 76. Which one of the following explain, why propene undergo electrophilic addition with HBr, but not
B

with HCN ?
(a) Br- is better nucleophile than CN-
(b) HBr being better source of proton as it is stronger acid than HCN
(c) HCN attacks preferentially via lone pair of nitrogen
(d) The C—Br bond being stronger is formed easily as compared to C—CN bond.

Q 77. The reaction is an example of :

(a) nucleophilic substitution (b) electrophilic addition
(c) elimination reaction (d) nucleophilic addition

Q 78. The substitution raction among the following is :

(a) (b)

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A
 (c) (d)

Q 79. The addition reaction among the following is :

(a) (b)

(c) (d) all of the above

Q 80. Which of the following is elimination reaction ?

LS
(a) CH3CH2Cl + aq. KOH  CH3CH2OH (b) IA
R
TO
T U
JI

(c) (d) None of the above

LA

Q 81. Acetaldehyde is the rearrangement product of:

(a) methyl alcohol (b) allyl alcohol (c) vinyl alcohol (d) all of the above
A

Q 82. Which one of the following reaction is possible ?

B

(a) CH3CH2CH3 + OH-  CH3CH2OH + CH 3

(b)

(c)

(d)

Q 83. Consider the above written reaction. The product is:

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 (a) (b)

(c) (d)

Q 84. Which of the following is most reactive towards elimination reaction?

(a) RCOO- (b) CN- (c) NO 3 (d) RO-

Q 85. Which of the following show fastest reaction with AgNO3 ?

(a) CH3CH = CHCl (b) CH2 = CHCH2Cl (c) CH3CH2CH2Cl (d)

Q 86. Which of the following belongs to –I group?

(a) –C6H5 (b) –CH3 (c) –CH2CH3 (d) – C(CH3)3

LS
Q 87. Which of the following acids has the smallest dissociation constant ?
(a) CH3CHFCOOH (b) FCH2CH2COOH (c) BrCH2CH2COOH (d) CH3CHBrCOOH

IA
Q 88. t-Butyl chloride reacts with OH- by S N 1 mechanism and rate  [t butyl chloride]. One of the reasons
R
for this is that :
TO

(a) stereochemical inversion takes place

(b) t-butyl carbocation is first formed which is more stable
(c) the product t-butyl alcohol is more stable
U

(d) the intermediate t-butyl carbocation is stabilized by salvation

T

Q 89. Identify the set of reagents/reaction conditions ‘X’ and ‘Y’ in the following set of transformations:
JI
LA
A

(a) X = dil. aq. NaOH, 20°C, Y = HBr

(b) X = cone. alcoholic NaOH, 80° C, Y = HBr, CH3COOH, 20°C
B

(c) X = dil. aq. NaOH, 20°C, Y = Br2, CHCl3, 0°C

(d) X = conc. alc. NaOH, 80°C, Y = Br2, CHCl3 0°C

Q 90. The nodal plane in the -bond of ethene is located in:

(a) the molecular plane
(b) a plane parallel to the molecular plane
(c) a plane perpendicular to the molecular plane which bisects the carbon-carbon sigma bond at right
angle.
(d) a plane perpendicular to the molecular plane which contains the carbon-carbon sigma bond.

Q 91. Which of the following represents the given mode of hybridization sp2 – sp2 –sp-sp from left to
right ?
(a) CH2 = CH – C  CH (b) HC  C – C  N

(c) CH2 = C – C = CH2 (d)

Q 92. Which of the following is elimination reaction ?

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 (a)
(b) CH3CH2Cl + aq. KOH  CH3CH2OH

(c)

(d)

Answers
1. c 2. a 3. c 4. d 5. a 6. b 7. d
8. b 9. d 10. b 11. b 12. d 13. d 14. b
15. c 16. a 17. a 18. a 19. a 20. a 21 c

LS
22. a 23. b 24. d 25. a 26. a 27. b 28 a
29. c 30. d 31. a 32. d 33. c 34. b 35. a
36.
43.
a
c
37.
44.
d
b
38.
45.
a
a
39.
46.
b
d IA
40.
47.
d
a
41.
48.
a
b
42.
49.
a
a
R
50. a 51. b 52. c 53. a 54. d 55. d 56. a
TO

57. d 58. a 59. c 60. c 61. d 62. a 63. c

64. d 65. d 66. d 67. a 68. c 69. b 70. d
U

71. c 72. d 73. c 74. c 75. a 76. b 77. b

78. c 79. b 80. c 81. c 82. c 83. b 84. d
T

85. b 86. a 87. c 88. b 89. b 90. c 91. a

JI

92. a 93. c 94. b 95. c

LA
A
B

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