Parth Ashram Ahmedabad 1

CHEMISTRY
C Co ou ur rs se e : : A AI IE EE EE E/ / I II IT T

SARMAS IIT
THRESHOLD

G Gr ra an nd d A As ss si ig gn nm me en nt t





BASIC PRINCIPLES AND REACTION MECHANISM




Level I
1. Which of the following contains three pairs of electrons in the valence shell ?
(a) Carbocations (b) Carbanions (c) Free radicals (d) None
2. Heterolysis of carbon-chlorine bond produces
(a) Two free radicals (b) Two carbanium ions
(c) Two carbanions (d) one cation and one anion.
3. Which of the following has all carbon atoms sp-hybridized ?
(a)
3 3
CH CH CH CH = (b)
3 3
CH C C CH
(c) CH C C HC (d) All the three
4. The Cl C Cl angle in 1, 1, 2, 2-tetrachloroethene and tetrachloromethane respectively will
be about
(a) 120
o
and 109 5 (b) 90
o
and 109 5
o
(c) 109 5
o
and 90
o
(d) 109 5
o
and 120
o
.
5. The typical reaction of olefinic bond is
(a) Electrophilic substitution reactions (b) Electrophilic addition reactions
(c) Nucleophilic substitution reactions (d) Nucleophilic addition reactions.
6. Which of the following possesses sp-carbon in its structure ?
(a)
2 2
CH CH CCl CH = = (b)
2 2
CCl CCl =
(c)
2 2
CH C CH = = (d) . CH CH CH CH
2 2
= =
7. Cyclic hydrocarbon A has all the carbon and hydrogen atoms in a single plane. All the
carbon-carbon bonds have the same length, less than 1 54 , but more than 134 . The CCC
bond angle will be
(a) 109
o
28' (b) 100
o
(c) 180
o
(d) 120
o
8. The shortest C C bond distance is found in
(a) Diamond (b) Ethane (c) Benzene (d) Acetylene.
9. An hybrid -
3
sp orbital contains
(a) 1/4 s-character (b) 1/2 s-character (c) 1/3 s-character (d) 2/3 s-character
10. What hybrid orbitals will from the following compound ?
3 2 3
CH CH CH CH CH =
(a) sp and
3
sp (b)
2
sp and
3
sp (c) sp and
2
sp (d) only
3
sp
11. Number of t-electrons in naphthalene is
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(a) 4 (b) 3 (c) 10 (d) 14
12. A straight chain hydrocarbon has the molecular formula C
8
H
10
. The hybridization of the
carbon atoms from one end of the chain to the other are respectively
sp sp sp sp sp sp sp , , , , , ,
2 2 3 2 2 3
and sp. The structural formula of the hydrocarbon would be :
(a)
2 2 3
CH CHCH CH CCH C CH = = (b) CH CHC CHC CH CH CH
2 3
= =
(c)
2 2 3
CH CCH C CHCH CH CH = = (d) CH. CHC CH CHCH CH CH
2 3
= =
13. Which of the following statements is not correct ?
(a) Double bond is shorter than a single bond
(b) Sigma bond is weaker than a t (pi) bond
(c) Double bond is stronger than a single bond
(d) Covalent bond is stronger than hydrogen bond.
14. The most stable free radical among the following is
(a)
2 2 5 6
CH CH H C (b)
3 5 6
CHCH H C (c)
2 3
CH CH (d)
3 3
CHCH CH
15. Which of the following is the most stable carbocation (carbonium ion) ?
(a)
+
2 3
CH CH (b) H C ) (CH
2 3
+
(c)
+
C ) (CH
3 3
(d)
2 5 6
H C H C
+

16. Which of the following is not a nucleophile ?
(a)

CN (b)

OH (c) NH
3
(d) BF
3
17. Which is the correct symbol relating the two Kekule structures of benzene ?
(a)

(b) (c) (d)

18. When the hybridization state of carbon atom changes from
3
sp to
2
sp and finally to sp, the
angle between the hybridized orbitals
(a) decreases gradually (b) decreases considerably
(c) is not affected (d) increases progressively
19. The maximum number of carbon atoms arranged linearly in the molecules,
2 3
CH CH C C CH = is
(a) 5 (b) 4 (c) 3 (d) 2
20. Aromatic character of benzene is proved by
(a) Resonance theory (b) Aromatic sextet theory
(c) Orbital theory (d) All the above
21. Which of the following statement is false about resonance contribution structures ?
(a) Contributing structures contribute to the resonance hybrid in proportion of their relative
energies
(b) Equivalent contributing structures make the resonance very important
(c) Contributing structures represent molecules having no real existence
(d) Contributing structures are less stable than the resonance hybrid.
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22. In which of the compounds given below is there more than one kind of hybridization
) , , (
3 2
sp sp sp for carbon ?
(i)
3 2 2 3
CH CH CH CH (ii)
3 3
CHCH CH CH = (iii)
2 2
CH CH CH CH = =
(iv) H C C H
(a) (ii) (b) (iii) and (iv) (c) (i) and (iv) (d) (ii) and (iii)
23. The change in the state of hybridization of the asterisked carbon in the following reaction
2
*
3
2
*
3
ONH C CH
O H
N C CH is
(a)
3
sp to
2
sp (b)
3
sp to sp (c) sp to
2
sp (d)
2
sp to
3
sp
24. Which of the following will show aromatic behaviour ?
(a) (b) (c) (d)
+

25. The bond length between
3
sp -hybridized carbon and other carbon atom is minimum in
(a) Propane (b) Propyne (c) Propene (d) Butane
26. The order of decreasing stability of the carbanions
; (II) CH ) (CH ; (I) C ) (CH
2 3 3 3

(IV) CH H C ; (III) CH CH
2 5 6 2 3

is
(a) I > II > III > IV (b) IV > III > II > I (c) IV > I > II > III (d) I > II > IV > III
27. The most stable carbonium ion among the following is
(a)
5 6 5 6
H HC C H C
+
(b)
2 5 6
H C H C
+
(c)
2 3
H C CH
+
(d)
2 2 5 6
H C CH H C
+

28. The reaction,
3 3 3 2
CH CHBr CH BHr CH CH CH + = is
(a) Nucleophilic addition (b) Electrophilic substitution
(c) Electrophilic addition (d) Free radical addition
29. Electrophile in the case of chlorination of benzene in presence of FeCl
3
is
(a)
+
Cl (b)

Cl (c) Cl (d) FeCl

3
30. In which of the following, resonance will be possible ?
(a) CH
2
= CH CH
2
CHO (b) CH
2
= CH CH = O
(c) CH
3
COCH
3
(d) CH
2
= CH CH
2
CH = CH
2
31. The percentage of s-character of the hybrid orbitals in etane, ethane and ethyne are
respectively.
(a) 50, 75, 100 (b) 10, 20, 40 (c) 25, 33, 50 (d) 25, 50, 75
32. In which of the following, the bond length between carbon and carbon is equal.
(a) 2-Butene (b) Benzene (c) 1-Butene (d) Propyne
33. The number of t-and o-bonds in benzene is
(a) 3t + 12 o (b) 12t + 12o (c) 6t + 11o (d) 6t + 6o
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34. Which of the following is not aromatic ?
(a) Benzene (b) Cyclooctatetraenyl dianion
(c) Tropylium ion (d) Cyclopentadienyl cation.
35. The cylindrical shape of alkyne is due to
(a) three sigma C-C bonds (b) three t C-C bonds
(c) two o C-C and one t C-C bonds (d) one sigma C-C and two t C-C bonds
36. Select the molecule which has only one t-bond.
(a) HC CH (b) CH
2
= CCHO (c) CH
3
CH = CH
2
(d) CH
3
C = CHCOOH
37. The hybridization involved in six carbon atoms of benzene is
(a) Three
3
sp and three
2
sp (b) Three
2
sp and three sp
(c) All six sp (d) All six
2
sp
38. Which of the following species would be expected to exhibit aromatic character ? Select the
correct answer from the following :
+
..
..
_
_
+

I. II. III. IV.
(a) I and IV (b) II and IV (c) I and III (d) II and III
39. Which of the following is correct regarding the I-effect of the substitutents ?
(a) F OR NR
2
< < (b) F OR NR
2
< >
(c) F OR NR
2
> < (d) F OR NR
2
> >
40. Which of the following is an electrophile ?
(a) H
2
O (b) NH
3
(c) AlCl
3
(d) C
2
H
5
NH
2

41. Pont out the incorrect statement about resonance ?
(a) Resonance structures should have equal energy
(b) In resonance structures, the constituent atoms must be in the same position
(c) In resonance structures, there should not be same number of electron pairs
(d) Resonance structures should differ only in the location of electrons around the constituent
atoms.
42. Intermediate involved in Reimer-Tieman reaction is
(a) Carbocation (b) Carbanion (c) Carbene (d) Free radical
43. Which of the following is not aromatic ?
(a) Benzene (b) Pyridine (c) Pyrimidine (d) 1, 4-Dioxane
44. Bond length of ethane (I), ethane (II), acetylene (III) and benzene (IV) follows the order :
(a) I > IV > II > III (b) I > II > IV > III (c) I > II > III > IV (d) III > IV > II > I

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45. The type of hybridizations exhibited by carbons in
CH = CH CH
2
COOH are

(a)
3
sp and sp (b)
2
sp only (c)
3
sp and
2
sp (d)
3
sp ,
2
sp and sp.
46. The structural formula of a compound is . CH C CH CH
2 3
= = The types of hybridization at
the four carbons from left to right are
(a)
3 2 2 2
, , , sp sp sp sp (b)
2 2 3 2
, , , sp sp sp sp (c)
2 2 3
, , , sp sp sp sp (d)
2 2 2 3
, , , sp sp sp sp .
47. The chemical system that is non aromatic is
(a) (b) (c)
+
(d)
+
_

48. Which of the following is planar in shape ?
(a) Methane (b) Acetylene (c) Benzene (d) Isobutane
49. The number of sigma and pi-bonds in 1-butene 3-yne are
(a) 5 sigma and 5 pi (b) 7 sigma and 3 pi (c) 8 sigma and 2 pi (d) 6 sigma and 4 pi
50. The ratio of t- to o-bonds in benzene is
(a) 1 : 4 (b) 1 : 2 (c) 3 : 1 (d) 1 : 6
51. The structure of H
2
C = C = CH
2
is
(a) linear (b) planar
(c) non-planar (d) has several resonance structures
52. How many primary carbon atoms are there in
3 2 2 2 3 3 2 3
CH CH CH ) )C(CH CH(CH CH CH ?
(a) 3 (b) 4 (c) 5 (d) 6
53. 2-Pentene contains
(a) 15 o-and one t-bond (b) 14 o- and one t-bond
(c) 15 o- and two t-bond (d) 14 o- and two t-bond
(e) 14 o- and no t-bond
54. Which among the following is aromatic ?
2-
_

I II III IV V
(a) I (b) II (c) III (d) IV (e) V
55. Toluene has
(a) 6 o- and 3 t-bond (b) 9 o- and 3 t-bond
(c) 9 o- and 6 t-bond (d) 15 o- and 3 t-bond
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56. The number of pi-bonds in CH C CH CH CH CH
2
= = is
(a) 2 (b) 5 (c) 4 (d) 3
57. The compound which contains all the four 1
o
, 2
o
, 3
o
and 4
o
carbon atoms is
(a) 2, 3-Dimethylpentane (b) 3-Chloror-2, 3-dimethylpentane
(c) 2, 3, 4-Trimethylpentane (d) 3, 3-Dimethylpentane.
58. In which of the following species, all types of hybrid carbons are present ?
(a)
2 2
CH C CH = = (b)
+
=
2 3
CH CH CH CH
(c)
+

2 3
CH C C CH (d)

=
2 3
CH CH CH CH
59. Among the following alkenes ;
1-butene; cis-2-butene; trans-2-butene
I II III
the decreasing order of stability is
(a) III > II > I (b) III > I > II (c) I > II > III (d) II > I > III
60. The addition of HCN to a carbonyl compound is an example of
(a) nucleophilic substitution (b) electrophilic addition
(c) nucleophilic addition (d) electrophilic substitution.
61. For the relation of phenol with CHCl
3
in presence of KOH, the electrophile is
(a)
2
CHCl
+
(b)
2
CCl : (c)
2
HCl C
-
(d) CCl
4

62. In which of the following hymolytic bond fission takes place
(a) Alkaline hydrolysis of ethyl chloride (b) Addition of HBr to double bond
(c) Potochlorination of methane (d) Nitration of benzene.
63. Among the following, the true property about
3
3
3
CH C
CH
CH

+
is
(a) non-planar (b) C
+
is
2
sp -hybridized
(c) electrophile can attack C
+
(d) does not undergo hydrolysis
64. Consider the following carbocations
I.
2 5 6
H C H C
+
II.
2 2 5 6
H C CH H C
+
III.
3 5 6
HCH C H C
+
IV.
2 3 5 6
) (CH C H C
+

The correct sequence for the stability of these is
(a) II < I < III < IV (b) II < III < I < IV (c) III < I < II < IV (d) IV < III < I < II
65. Intermediates formed during reaction of
2
NH
O
||
C R with
2
Br and KOH are
(a) RCONHBr and RNCO (b) RNHCOBr and RNCO
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(c) RNH-Br and RCONHBr (d) RCONBr
2
66. Acetaldehyde is the rearrangement product of
(a) Methyl alcohol (b) Allyl alcohol (c) Vinyl alcohol (d) All are correct
67. In the mechanism of Hoffmann reaction which intermediate rearranges to alkyl isocyanate?
(a) Bromamide (b) Nitrene (c) Nitroso (d) Amide
68. Which of the following is most stable ?
(a)
+
C Ph
3
(b)
+
CH Ph
2
(c)
+
2
PhCH (d) Tropylium cation
69. Select the most stable carbocation from among the following :
(a)
+
(b)
+

(c)
+
(d)
+

70. Which of the following carbon atoms is most electronegative ?
III II I
C CH CH
2 3
CH
(a) I (b) II (c) III (d) all are equally electronegative
71. The heat of hydrogenation of 1-hexene is 126 kJ . mol
1
When a second double bond is
introduced in the molecule, the heat of hydrogenation of the resulting compound is 230 kJ
1
mol

. The resulting compound (diene) is

(a) 1, 3-Hexadiene (b) 1, 4-Hexadiene (c) 1, 5-Hexadiene
(d) cannot predict from the given information
72. In benzene, all the six C-C bonds have the same length because of
(a) Tautomerism (b)
2
sp -Hybridization (c) Isomerism (d) Inductive effect
73. Three fused benzene rings are found in
(a) Naphthalene (b) Anthracene (c) Phenanthroline (d) Triphenylmethane
(d) none of the above
74. In which of the following compounds, the underlined carbon has
3
sp -hybridization ?
(a) OOH C CH
3
(b) OH H C CH
2 3
(c)
2 3
ONH C CH (d)
2 3
CH H C CH =
75. Resonance in most of the organic molecules
(a) increase stability (b) decreases stability (c) increases reactivity (d) none
76.
3 2
CH
..
: O
||
C CH :

and
3 2
..
: :
|
CH
O
C CH

= are
(a) Resonating structures (b) Tautomers
(c) Geometrical isomers (d) Optical isomers
77. The arrangement of , CH ) (CH , C ) (CH
2 2 3 3

2 3
CH CH when attached to benzene or an
unsaturated group in increasing order of inductive effect is
(a) < <
2 3 2 3 3 3
CH CH C ) (CH C ) (CH (b) < < C ) (CH CH ) (CH CH CH
3 3 2 3 2 3

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(c) < <
2 3 3 3 2 3
CH CH C ) (CH CH ) (CH (d) < < CH ) (CH CH CH C ) (CH
2 3 2 3 3 3

78. Which of the following statements regarding the resonance energy of benzene is correct ?
(a) The energy required to break the C-H bond in benzene
(b) The energy required to break the C-C bond in benzene
(c)The energy is a measure of stability of benzene
(d) The energy required to convert

79. The reaction, OH C ) (CH
O H
Br C ) (CH
3 3
2
3 3
is
(a) elimination reaction (b) substitution reaction
(c) free radical reaction (d) addition reaction
80. Most stable carbanion is
(a)

2 3
CH CH (b)

CH ) (CH
2 3
(c)

C ) (CH
3 3
(d)

2 5 6
CH H C

Level II
81. The bonds between carbon atom (1) and carbon atom (2) in compound
2
H
3
C H
2
C
1
C N = involves the hybrid as
(a)
2
sp and
2
sp (b)
3
sp and sp (c) sp and
2
sp (d) sp and sp
82. The formation of cyanohydrin from a ketone is an example of
(a) Electrophilic addition (b) Nucleophilic addition
(c) Nucleophilic substitution (d) Electrophilic substitution.
83. The compound in which C uses only is
3
sp -hybrid orbitals for bond formation is
(a) HCOOH (b) CO N) (H
2 2
(c) COH ) (CH
3 3
(d) CHO CH
3

84. The enolic form of acetone contains
(a) Nine o-bonds, one t-bond and two lone pairs
(b) Eight o-bonds, two t-bonds and two lone pairs
(c) Nine o-bonds, one t-bond and one lone pair
(d) Nine o-bonds, two t-bonds and one lone pair
85. The C-C bond length of the following molecules is in the order :
(a)
2 2 6 6 4 2 6 2
H C H C H C H C > > > (b)
6 2 6 6 4 2 2 2
H C H C H C H C < < <
(c)
4 2 6 6 2 2 6 2
H C H C H C H C > > > (d) . H C H C H C H C
6 6 2 2 6 2 4 2
> > >
86. The hybridization of carbon atoms in C-C single bond of HC C CH = CH
2
is
(a)
3 3
sp sp (b)
3 2
sp sp (c)
2
sp sp (d) sp sp
3

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87. Number of t-electrons in cyclobutadienyl anion
2
4 4
) H (C is
(a) 2 (b) 4 (c) 6 (d) 8
88. Homolytic fission of C-C bond in ethane gives an intermediate in which carbon is
(a)
3
sp -hybridised (b)
2
sp -hybridised (c) sp-hybridised (d)
2
sp d-hybridised
89. Which one of the following has the smallest heat of hydrogenation per mole ?
(a) 1-Butene (b) trans-2-Butene (c) cis-2-Butene (d) 1, 3-Butadiene.
90. The kind of delocalization involving sigma bond orbitals is called
(a) Inductive effect (b) Hyperconjugation effect
(c) Electromeric effect (d) Mesomeric effect.
91. The most unlikely representation of resonance structures of p-nitrophenoxide ion is
(a)
N
+
O
O
O
_
_
(b)
N
+
O
O
O
_
_
(c)
N
+
O
O
O
_
(d)
N
+
O
O
O
_

92. In compound, H, C CH CH CH CH
2 2 2
= the
3 2
C C bond is of the type
(a)
2
sp sp (b)
3 3
sp sp (c)
3
sp sp (d)
3 2
sp sp
93. Polarization of electrons in acrolin may be written as
(a) O

CH CH

CH
2
=
+
=

(b)
+
= =

CH
2
CH CH
(c) O CH

CH

CH
2
=

(d)

= =
+

O

CH
2
CH CH
94. Which of the following has the highest nucleophilicity?
(a)

F (b)

OH (c)

3
CH (d)

2
NH
95. Which of the following represents the given mode of hybridization sp sp sp sp
2 2
from
left to right ?
(a) N C CH C H
2
= (b) CH C C HC
(c)
2 2
CH C C C H = = = (d)
H C
2
CH
2

96. An aromatic molecule will
(a) have 4 n t-electrons (b) have (4n + 2) t-electrons
(c) be planar (d) be cyclic.


Parth Ashram Ahmedabad 10

97. Examine the following two structures for the anilinium ion and choose the correct statement
from the ones given below :
NH
3
NH
3
+
+
I
II

(a) II is not an acceptable cannocal structure because carbonium ions are less stable than
ammonium ions
(b) II is not an acceptable canonical structure because it is non-aromatic
(c) II is not an acceptable canonical structure because nitrogen has 10 valence electrons
(d) II is an acceptable canonical structure.
98. The most stable carbonium ion is
(a)
+
2 3
CH CH (b)
+
CH ) (CH
2 3
(c)
+
C ) (CH
3 3
(d)
+

2 3 3
CH C ) (CH
99. Which of the following compounds possesses the CH bond with the lowest bond dissociation
energy ?
(a) Toluene (b) Benzene (c) n-Pentane (d) 2, 2-Dimethylpropane
100. Which of the following intermediate has the complete octet around the carbon atom ?
(a) carbonium ion (b) carbanion (c) free radical (d) carbene















Parth Ashram Ahmedabad 11



Grand Assignment

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