VELAMMAL KNOWLEDGE PARK, PONNERI

BODHI CAMPUS – IIT/NEET ACADEMY

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IIT - WORK SHEET
Class: XII Subject: Chemistry
Topic: GENERAL ORGANIC CHEMISTRY (G.O.C)
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 Multiple Choice Questions:
Electronic Effects :
1. Arrange the following alkenes in increasing order of enthalpy of hydrogenation
(take numerical value only)

(P) (Q) (R) (S)

A) R  S  Q  P B) R  S  P  Q C) P  Q  R  S D) P  Q  S  R
2. –CCl3 group attached to benzene ring act as meta directing and deactivating due to
A) Resonance effect B) Hyperconjugation
C) Reverse hyperconjugation D) Electromeric effect
3. Which of the following group show +M effect?
 C  OR
A) –BH2 B)  C H 2 C) NH 2 D) ||
O
4. Which of the following exhibit d-orbital resonance?
  ()
A) Ph  N H 3 B) Ph  P H 3 C) ph  OH D) C F3
5. Which group will show highest –I effect?

A) NO 2 B) SO 3H C) CN D)  N H 3
6. In which of the following linear conjugation is absent?

A) B) C) D)

7. Delocazation of positive charge is possible in 

H NH3
|
N
A)  B) C) D)
N N 
H N
|
H H H
8. Most stable resonating structure of dizomethane (CH2N2) is
   
A) CH 2  N  N B) CH 2  N  N  C) C H 2  N  N D) All are equally stable
9. Which of the following can act as a nucleophile and an electrophile?
A) CH 3  NH 2 B) CH 3Cl C) CH 3OH D) CH 3CN
10. Which of the following has inductive and mesomeric effect?
A) CH 3  Cl B) CH 3  CH  CH 2
C) CH 3  CH  CH  CH  0 D) CH 2  CH  CH  CH 2

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11. Which of the following resonance structures is the major contributor to the
resonance hybrid?
  
CH 3  CH 2  C H  O Me  CH 3  CH 2  CH  O Me
 
A) I B) II
C) Both have equal contribution D) They are not resonance structures
12. Arrange the following in increasing order of stability :

A) I < II < III B) II < I < III C) I < III < II D) II < III < I
13. Increasing order of the stability of the following is :

A) I > II > III > IV B) I > III > II > IV C) I > IV > III > II D) IV > III > II > I
14. The length of the carbon-carbon single bond of the compounds
(I) CH 2  CH  C  CH (II) CH  C  C  CH
(III) CH 3  CH  CH 2 (IV) CH 2  CH  CH  CH 2
is expected to decrease in the order :
A) III > II > I > IV B) I > III > II > IV C) III > IV > I > II D) II > IV > I > III
15. Which of the following molecules has longest C = C length?

16. Consider the following three amines,

Arrange C––N bond length of these compounds in decreasing order :

A) 1 > 2 > 3 B) 1 > 3 > 2 C) 3 > 2 > 1 D) 2 > 3 > 1

17. Which group will show highest + I effect?

A) COO B) D C) O D) (CH 3 )3 C 
18. Which of the following is incorrect about inductive effect?
A) It is a permanent effect
B) It involves complete transfer of sigma electrons
C) It is distance dependent effect
D) C-H sigma bond is taken as reference for this effect

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19. Which of the following is an ambident nucleophile?

 
A) NO2 B) N H 4 C) CN D) Both A and C
20. The groups which exert –I effect only
A)  NH3 B) CCl3 C) CF3 D) All of these
21. Which of the following is strong +I group
A) C6 H 5 B) CH 3 C)  CH3 2 CH  D)  CH3 3 C 
22. Which of the following orders is correct regarding the -I effect of the substituents?
A)  NF3   NO2  CN  Cl B)  NO2  CN   NF3  Cl
C) CN   NO2  Cl   NF3 D)  NF3  Cl   NO2  CN
23. Which of the following is an incorrect statement about inductive effect?
A) The electron-withdrawing inductive effect (-I) of a group weakens the O-H bond
in -COOH and favours ionisation of a carboxylic acid
B) It operates through space.
C) Aniline is a weaker base than ammonia due to negative inductive effect shown
by the phenyl group.
D) Alkyl groups are good examples of positive inductive effect.
24. The molecule which has the shortest carbon-oxygen bond length is –
A) CH3–CH2–CHO B) CH2 = CH-CHO
C) CH3–O–CH = CH2 D) CH3 – CH2OH
25. Which is the least stable resonance structure among the following?

26. Which of the following has the least stable resonating structure?

27. Which of the following molecules, does not have the mesomeric effect with the
benzene nucleus?

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28. Which of the following exhibit +R effect?
A) –NO2 B) –CHO C) –OH D) –COOH
29. Which of the following is the incorrect statement about resonance
A) It decreases the energy of the system.
B) The position of atoms change due to resonance.
C) Resonance hybrid is more stable than any resonating structure.
D) Resonating structures cannot be isolated at any temperature.
30. Incorrect order of +I effect is

31. Electromeric effect can be observed in

A) (CH3)2O B) C2H5OH C) C2H6 D) C2H4
32. Which is not correct in hyper conjugation effect?
A) This effect is also known as no-bond resonance
B) Stability of (CH3)3C+, (CH3)2CH+ and CH3CH2+carbocations can be explained by
this effect
C) This effect is not possible in alkenes
D) This effect is also possible in alkyl arenes
33. Out of the given substituent groups, which one shows +R effect?
A) –COOH B) –NH2C) >C=O D) –CN
34. Most stable carbocation among the following is

35. Which of the following compounds will exhibit d-orbital resonance?

36. Which of the following pairs of structures does not represent resonating
structures?

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37. The C- Cl bond length is shortest in:

38. Match the following :

Column – I Column - II
(I)  - empty orbital (P)
conjugation
(II)  -lone pair conjugation (Q)
B
(III) Linear conjugation (R) H

(IV) Cross conjugation (S)

O
O
(I) (II) (III) (IV) (I) (II) (III) (IV)
A) P Q R S B) S R Q P
C) Q S P R D) Q S R P
39. In which of the following benzene is most activated by hyperconjugation?

40. In which of the following molecules all the effects namely inductive, mesomeric
and hyperconjugation operate?

41. Find out anti aromatic compound among the following :

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42. Which of the following is incorrect statement?
A) Equal breaking of a covalent bond is known as homolysis
B) Homolysis occurs in presence of light
C) Heterolysis favoured in polar solvents
D) Homolysis of a covalent bond requires more energy than heterolysis
43. Which of the following acts as an ambident nucleophile?

A) CN  B) Cl  C) H 2 O D) SO3
44. Which of the following statements are correct?
I) Inductive effect is a permanent effect
II) Inductive effect involves sigma electrons.
III) Inductive effect is distance dependent
IV) Alkyl groups generally act as +I groups
A) I, III & IV only B) II, III& IV only C) I, II, IV only D) I, II, III & IV
45. Match the following:
COLUMN – I COLUMN - II
(I) Ambident Nucleophile P) CH3CN
(II) Electrophile Q) CH3OH
(III) Ambiphile R) NO 2
(IV) Neutral nucleophile S) CH3

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

A) P Q R S B) R S P Q
C) R P Q S D) P R S Q
46. Hyperconjugation involves overlap of :
A)    B)    C) p  p D)   
47. Out of the following four compounds

aromatic compounds are :

A) 1, 4 B) 1, 2, 4 C) 2, 4 D) 2, 3, 4
48. Which of the following is temporary electronic effect :
A) Inductive effect B) Mesomeric effect
C) Hyper conjugation D) Electromeric effect
49. Give the number of ligands which are monodentate as well as ambidentate

A) 4 B) 3 C) 2 D) 6
50. In which of the following delocalisation of positive charge is possible ?

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Reaction Intermediates :
51. Which of the following carbocation does not undergo rearrangement?
+
+ CH2 +
+
A) CH2 B) C) CH3 D) CH 2

CH3
52. Which of the following is most stable carbanion ?
A) CH 3  CH 2 B) CH 2  CH C) HC  C D) CH3  CH  CH 3
53. Which of the following is anti aromatic?

A) B) C) D) All of these
- of the following order is correct for +the stability of these carbocation?
54. Which
  
C H2  F C H 2  Cl C H 2  Br
I II III
A) I II III B) III  II  I C) I  III  II D) II  III  I
55. The most stable free radical among the following is
   
A) C H 3 B) CH 3  C H 2 C) CH 3 2 C H D) CH 3 3 C
56. Which of the following is incorrect statement?
A) The hybridization of carbon in singlet carbine is sp2.
B) Triplet carbine is paramagnetic.
C) Singlet carbene has one lone pair of electrons.
D) Singlet carbine is morestable than triplet carbine
57. The carbanion which is most stable is
CH2 CH2 CH2 CH2
NO2
A) B) C) D)
NO2
58. Which of the following is incorrect statement?
A) Benzyne is aromatic NO2
B) In benzyne all the carbon atoms are sp2 hybridised
C) In benzyne two carbon atoms are sp hybridised
D) Benzyne has six delocalized pi electrons.
59. Which ring is electron rich in azulene

A) Five membered ring B) Six membered ring

C) Both rings are equally rich D) Both rings are electron deficient
60. Least stable carbanion among the following :
A) HC  C B) C6H 5 3 C C) CH 3 3 C D) CH 3
61. The most stable carbocation is
CH3  CH3 CH3
CH2
 
A) B) C) D)

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62. The correct order of stability of the following carbocations is
  
CH 3  O  C H 2 CH 3  NH  C H 2 CH 3  S  C H 2
x y z
A) x > y > z B) y > x > z C) z > x > y D) y > z > x
63. Which of the following group show +M effect?
 C  OR
A) –BH2 B)  C H 2 C) NH 2 D) ||
O
64. The most stable free radical among the following is

  Ph  C  CH 3 .
A) Ph  C H 2 B) Ph  C H  CH 3 C) | D) CH2
CH 3

65. The order of decreasing stability of the following cations is

  
CH 3  C H  CH 3 CH 3  C H  OCH 3 CH 3  C H  COCH 3
I II III
A) II > I > III B) I > II > III C)II > III > I D) III > I > II
66. Consider the following carbanions :

Correct decreasing order of stability is :

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

67. Correct order of stability for the following radicals is :

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

68. The most stable resonating structure is

 
A) H 2 N  C H  CH  CH  OCH 3 B) H 2 N  CH  CH  CH  OCH 3
   
C) H 2 N  CH  CH  CH  O CH 3 D) H 2 N  CH  C H  O CH 3
69. Which one of the following is most stable carbocation?
   
A) CH 2  CH  C H 2 B) C H 3 C) CH 3  CH  C H D) CH 3  C H 2
70. Which of the following compounds does not exhibit resonance?
CH2OH
A) CH3CH2OCH = CH2 B)

C) CH3CH2CH2CONH2 D) CH3CH2CH = CHCH2NH2

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71. Match the following :
Column-I (Properties) Column-II (Reaction intermediate)
A) Stability order : 3  2  1
o o o (p) Methyl carbocation
B) Stability order : 1  2  3
o o o (q) Alkyl carbocation
C) No hyperconjugation (r) Carbanion
D) Two unshared pair of electrons (s) Nitrene
A) A-r, B-q, C-p, D-s B) A-q, B-r, C-p, D-s
C) A-p, B-s, C-q, D-r D) A-s, B-p, C-q, D-r
72. Arrange the following cations in decreasing order of stability:

A) P > R > Q > S B) R > P > S > Q C) Q > R > P > S D) P > Q > S > R
73. Correct order of stability of following carbocations:

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

74. Arrange the following carbanions in decreasing order of stability:

A) P > Q > R > S B) S > Q > P > R C) S > Q > R > P D) Q > S > R > P
75. Arrange the following carbanions in the decreasing order of their stability.

A) Q > R > S > P B) R > Q > P > S C) S > P > R > Q D) P > Q > R > S
76. Find out correct representation of triplet carbene:

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77. In which of the following 2nd anion is more stable than first?

Acidic and Basic Strengths :

78. The correct basic strength of the following is in the order
I. p-fluro aniline II.p-chloro aniline III. P-bromo aniline
A) I > II > III B) III > II > I C) II > I > III D) II > III > I
79. The correct order of basic strength of the following is
I. Aniline II. o-nitro aniline
III. m-nitro aniline IV. P-nitro aniline
A) I>III>IV>II B) II>III>IV>I C) II>I>III>IV D) III>I>IV>II
80. Identify the strongest base among the following :

81. The strongest base among the following is

82. Which amino group in guanidine is a stronger base?

A) x B) y C) z D) All are equally base

83. The correct decreasing order of basic nature of amines is

CH 2  CH  CH 2  NH 2 CH 3  CH 2  CH 2  NH 2 HC  C  CH 2  NH 2
I II III
A) I > II > III B) II > III > I C) II > I > III D) III > I > II
COOH

84. pKa value of the compound decreases if X is :

X
A) –NO2 B) –NH2 C) –OH D) –OCH3
85. Under suitable conditions C6H5CH2OH (A) C6H5OH (B), and C6H5COOH (C) can
act as acids. The increasing order of their acidic strength is :
A) A < B < C B) A < C < B C) B < A < C D) C < B < A

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86. In which of the following pairs the first one is the weaker base than second.
 ⊝  
A) CH3COO , HCOO B) HO , NH2
⊝ ⊝
C) CH2 = CH:, H – C  C D) CH3NH2, CH3OH
87. Correct order of decreasing basic strength of the given compound is :

(I)  H3C 3 N (II)  H3C 2 NH (III) (IV)

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

88. Conjugate acid of a weak base is always stronger. What will be the decreasing
order of basic strength of the following conjugate bases?
OH , RO , CH3COO , Cl 
A) RO  OH   CH3COO  Cl  B) OH   RO  Cl   CH3COO
C) RO  CH3COO  Cl   OH  D) CH3COO  Cl   OH   RO
89. Which of the following will have the lowest pK a value?

90. The decreasing order of basic characters of the following is:

A) III > I > IV > II B) II > I > IV > II C) IV > III > II > I D) I > II > III > IV
91.

In the above structure correct order of basic strength of three nitrogen atoms
A) a > b > c B) b > a > c C) c > a > b D) c > b > a
92. Arrange the following acids in the decreasing order of their acidity :

A) Q > S > P > R B) P > R > S > Q C) R > Q > P > S D) S > Q > P > R
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93. Arrange the following carboxylic acids in increasing order of Ka value.

A) I < III < II B) III < I < II C) III < II < I D) I < II < III
94. The decreasing acidity order of following benzoic acid derivatives is

A) P > Q > R > S B) Q > P > S > R C) S > R > Q > P D) R > S > P > Q
95. Which of the phenol derivative is most acidic?

96. The correct order of decreasing order of basic strength?

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

97. Basic strength order of N–atoms ( a and b) is

A) a>b B) b>a C) a=b D) b>>a

98.

Arrange the following phenol in increasing order of pKa value.

A) I < II < III B) III < I < II C) III < II < I D) I < III < II
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99. Arrange the following in decreasing order of basic strength.
Cl  RCOO OH  RO NH 2
I II III IV V
A) I>II>IV>III>V B) V>IV>II>III>I C) I>II>III>IV>V D) V>IV>III>II>I
100. Which comparison is not correct as indicated?

Answer Key for Multiple Choice Questions

Q.No Key Q.No Key Q.No Key Q.No Key Q.No Key
1 A 11 B 21 D 31 D 41 B
2 C 12 C 22 A 32 C 42 D
3 C 13 A 23 B 33 B 43 A
4 B 14 C 24 A 34 D 44 D
5 D 15 D 25 B 35 B 45 B
6 A 16 A 26 D 36 A 46 B
7 A 17 C 27 D 37 A 47 B
8 B 18 B 28 C 38 C 48 D
9 D 19 D 29 B 39 A 49 A
10 C 20 D 30 B 40 C 50 C
Q.No Key Q.No Key Q.No Key Q.No Key Q.No Key

51 A 61 D 71 B 81 B 91 C

52 C 62 B 72 A 82 A 92 C

53 D 63 C 73 B 83 C 93 A

54 A 64 C 74 C 84 A 94 A

55 D 65 A 75 A 85 A 95 B

56 D 66 A 76 B 86 B 96 A

57 B 67 D 77 B 87 D 97 A

58 C 68 B 78 A 88 A 98 C

59 A 69 A 79 A 89 A 99 D

60 C 70 D 80 D 90 A 100 B

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 Numerical Questions:
1. In triplet carbene what is the maximum number of valence electrons that may
have same spin direction ?
2. The total number of Hyperconjugative structures possible for the following
cabocation is
CH3
+
C
CH3

3. How many of the following are stronger bases than Aniline?

p-methoxyaniline, m-methoxy aniline, o-toluidine, p-chloroaniline, p-toluidine
and o-nitroaniline, Benzylamine
4. Find out number of aromatic compounds (or) ions form the following:




H


5. Find out the number of compounds which are more stable in ionic structure.

6. The C – O bond order in CO32 is

7. How many of the following are nucleophiles.
H  , H  , CN  , NH 4 , PH3 , H 2O,

CH3 , Cl , OH  , N O2 , C2 H5OH, CH3  O  CH3 , AlCl3
8. How many of the following are electrophiles?
 
BCl3, NH3, CH4, AlCl3, CO2, SO3, NO2 , H+, CN  , BeCl2, H2O, NH 4
9. How many of the following are +I groups.
-NO2, -CH3, - CCl3, -CN, -CH2-CH3, O  , COO , OH , C  CH , CH  CH3 2 ,

C CH3 3

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10. Among the given sets, how many of the following does not represent the
resonating structure

11. How many groups (attached with benzene ring) can show +M effect ?

12. Among the following how many of them is/are more acidic than phenol?

HO NO2, HO CO2H, HCO2H, CH3COOH ,

OH COOH OH

, ,

NO2

13. There are ‘X’ + M groups and ‘Y’-M groups among the following. The value of X-Y
is
O

OCH 3 ,  NH 2 , OH ,  NHC  CH 3 ,  NO2 ,  N  CH 3 2 , CHO,  SH , CN ,  P H 3 ,  SCH 3

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14. Identify number of compound from following. Which lilberate CO2 on reaction
with NaHCO3.

15. How many of the following are more acidic than phenol?

16. How many of the following show    conjugation?

CH3CH=CH2, CH2=CH-CH=CH2, CH2=CH-OCH3, CH3CH+-OCH3 ,

..
, , .. , , , O
N ..
H

17. How many of the following are +R and also –I groups


–OH, –OCH3, –NO2, –COOH, –F, O , –CH3, –CHO, –COCH3,
–CN, –NH2, –NHCH3

18.

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19. How many of the following are more stable than Benzyl carbocation?

CH 3 CH 3

CH 3 C H 2 , CH 3  C H , CH 3  C  , , , , ,


CH 3
⊕ ⊕ ⊕
CH2 CH2 CH2

 
, , , CH 3 C HOCH 3 , CH 3  C H  NH 2

OH Cl CHO

20. Number of alpha hydrogens in the following structures I, II, III are x, y and z
respectively, then x + y – z = _____
.
CH-CH2-CH3
+
I II III

21. How many of the following species have only sp2 hybridised carbon(s)?
 - .  . -
CH3-CH2, CH3CH2, CH3CH2, CH2=CH-CH2, CH2, CH2,

- - 
CH2=CH-CH2, CH2=CH, , CH2,
22. How many of the following do not show ortho effect ?
COOH COOH COOH OH
CH3 OCH3 Cl CH3
, , , ,

OH COOH COOH COOH OH

Cl C2H5
, , , ,
OCH3 CH3
CH3
23. How many of the following are nucleophiles?
Cl - , CN - , NO2- , CH2=CH2 ,C6 H6 CH3CH3 , CO2 , SO3 ,BCl3
24. How many of the following are electrophiles but not lewis acids?
• • •
BF3 ,C H 3 , AlCl3 , CH 3 C H 2 , SO3 ,ZnCl2 , H + , Na+ , Al 3+ , CH 3CH 2 C H 2

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Topic : General Organic Chemistry Chemistry - IIT Work Sheet
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25. How many among the following has correct relation between a and b?(a & b are
bond lengths)

26. Number of species having six or more hyperconjugative structures are :

27. Find out number of compounds which are more stabilize in ionic structure, from
following :

Answer Key for Numericals

Q.No Key Q.No Key Q.No Key
1 4 11 5 21 7
2 6 12 6 22 5
3 3 13 3 23 5
4 7 14 5 24 3
5 3 15 4 25 1
6 1.33 16 3 26 3
7 9 17 4.75 27 3
8 7 18 5
9 6 19 7
10 4 20 10

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