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274 CHEMISTRY Organic Chemistry : Some Basic Principles and Techniques 275

17. The correct name for the following hydrocarbon is 29. The chirality of the compound
(a) Tricyclo [4.1.0] heptane Br
(b) Bicyclo [5.2.1] heptane
(c) Bicyclo [4.1.0] heptane C
(d) Bicyclo [4.1.0] hextane H is
1. The number of en antiomers of th e compound 8. The IUPAC name of the compound shown below is : 18. The Beilstein test for organic compounds is used to detect H3C Cl
(a) 3-bromo-1-chlorocyclohexene Cl (a) nitrogen(b) sulphur (c) carbon (d) halogens (a) R (b) S (c) E (d) Z
CH 3 CHBr CHBr COOH is : 19. Which of the following is an optically active compound ?
(b) 1-bromo-3-chlorocyclohexene 30. Among the following four structures I to IV,
(a) 2 (b) 3 (a) 1-Butanol (b) 1-Propanol
(c) 2-bromo-6-chlorocyclohex-1-ene CH3 CH3
(c) 4 (d) 6 (c) 2-Chlorobutane (d) 4-Hydroxyheptane O
(d) 6-bromo-2-chlorocyclohexene Br | || |
2. The IUPAC name of CH 3 - C º C - CH(CH 3 ) 2 is: 9. In Lassaigne test a violet colour obtained indicates the 20. An important chemical method to resolve a racemic mixture C 2 H 5 - CH - C3 H 7 , CH 3 - C - CH - C 2 H 5,
(a) 4-methyl-2-pentyne presence of makes use of the formation of ( II )
(a) a meso compound (b) enantiomers ( I)
(b) 4, 4-dimethyl-2-butyne (a) sulphur (b) halogen
(c) methyl isopropyl acetylene (c) nitrogen (d) None of these (c) diasteromers (d) racemates
H CH3
(d) 2-methyl-4-pentyne 10. IUPAC name of the compound is : 21. Lassaigne’s test is used in qualitative analysis to detect | Å |
3. Which pairs have same percentage of carbon? (a) nitrogen (b) sulphur H- C , C2H 5 - CH- C 2H5
O |
|| (c) chlorine (d) All of these
(a) CH 3COOH and C 6 H12O 6 22. The process of separation of a racemic modification into d H ( IV)
H - C - CH 2 - CH 2 - OCH 3
( III)
(b) CH 3COOH and C12 H 22O11 (a) 2 – methoxypropanal (b) methoxypropanal and l -enantiomers is called
(a) Resolution (b) Dehydration it is true that
(c) CH 3COOH and C 2 H 5OH (c) 3 – methoxypropanal (d) 2 – formyl methoxyethane
(c) Revolution (d) Dehydrohalogenation (a) only I and II are chiral compounds
11. The number of secondary hydrogens in 2, 2-dimethylbutane
(d) C 6 H12O 6 and C12 H 22O11 23. Tautomerism will be exhibited by (b) only III is a chiral compound
is :
(a) (CH3)2NH (b) (CH3)3CNO (c) only II and IV are chiral compounds
4. The IUPAC name of the compound : (a) 8 (b) 6 (c) 4 (d) 2
(c) R3CNO2 (d) RCH2NO2 (d) all four are chiral compounds
CH 2 - CH - CH 2 is 12. The geometrical isomerism is shown by
24. Lassaigne’s test for the detection of nitrogen fails in 31. Which of the following is optically inactive?
| | | CH2
CN CN CN CH2 H H
(a) NH 2 CONHNH 2 .HCl (b) NH 2 NH 2 .HCl
(a) 1, 2, 3-trinitropropane (a) (b) H 3C Cl Cl CH3
(c) NH 2CONH 2 (d) C 6 H 5 NHNH 2 .HCl (a) Cl CH3 (b) H C Cl
(b) 1, 2, 3-tricyanopropane 3
(c) 3-cyanopentane-1, 5-dinitrile 25. A compound of molecular formula of C7H16 shows optical H H
CHCl
(d) 1, 2, 3-pentanetrinitrile CCl2 isomerism, compound will be H
5. The IUPAC name of the compound (c) (d) (a) 2, 3-Dimethylpentane (b) 2,2-Dimethylpentane H 3C Cl
(c) 2, 4 - Dimethylpentane (d) None of these (c) H C Cl (d) none of these.
CH 3OCH 2 CH 2 CH 2 OCH 2 CH 3 is : ..
3
13. The IUPAC name for .. H
(a) 3-ethoxy-1-methoxypropane 26. CH2 – C – CH3 and CH2 = C – CH3 are 32. C8H16 that can form cis-trans geometrical isomers and also
|| |
(b) 1-ethoxy-3-methoxypropane :O has a chiral centre, is
C1 O . .:
(c) 2, 5-dioxyhexane |
CH3 - C - CH 2 - CH = CH - CH3 is (a) resonating structures (b) tautomers
(d) ethoxypropane oxymethane
| (c) geometrical isomers (d) optical isomers (a) H (b) H
6. The absolute configuration of the following :
H 27. Which of the following pairs of compounds are enantiomers?
CH3 (a) 5–chlorohex–2–ene CH3 CH3 (c) Both of these (d) None of these
H Cl (b) 2–chlorohex–5–ene HO H HO H 33. Which of the following will have a mesoisomer also?
is (c) 1–chloro–1–methylpent–3–ene (a) and
Cl H H OH HO H (a) 2, 3- Dichloropentane (b) 2, 3-Dichlorobutane
(d) 5–chloro–5–methylpent–2–ene CH3 CH3 (c) 2-Chlorobutane (d) 2-Hydroxypropanoic acid
C2H5 14. Among the following the most stable compound is :
CH3 CH3 34. Amongst the following compounds, the optically active
(a) 2S, 3R (b) 2S, 3S (a) cis-1, 2-cyclohexanediol alkane having lowest molecular mass is
(c) 2R, 3S (d) 2R, 3R H OH HO H
(b) trans-1, 2-cyclohexanediol (b) and
7. Which of the following compounds has wrong IUPAC name? HO H H HO H
(c) cis-1,3-cyclohexanediol
CH3 CH3 |
(a) CH3–CH2–CH2 –COO–CH2CH3 ® ethyl butanoate (d) trans-1, 3-cyclohexanediol (a) CH 3 - C -
15. Which of the following compounds contains 1°, 2°, 3° as CH3 CH3 |
(b) CH3 - CH - CH 2 - CHO ® 3-methyl-butanal
| well as 4° carbon atoms ? H OH HO H C2H 5
(c) and
CH3 (a) Neopentane (b) 2-methyl pentane HO H HO H
(c) 2,3-dimethyl butane (d) 2,2,3-trimethyl pentane CH3 CH3 CH3
(c) CH3 - CH - CH - CH3 ® 2-methyl-3-butanol 16. Correct configuration of the following is
|
| | CH3 CH3 (b) CH3 - CH 2 - CH - CH3
OH CH3 CH3 H OH H OH
(d) and (c) CH 3 - CH 2 - CH 2 - CH 3
HO H H OH
O H OH
|| CH3 CH3 (d) CH 3 - CH 2 - C º CH
(d) CH3 - CH - C - CH 2 - CH3 CH3 OH 28. Kjeldahl’s method is used in the estimation of 35. The most suitable method for separation of a 1 : 1 mixture of ortho
| and para nitrophenols is
CH3 (a) nitrogen (b) halogens
H (c) sulphur (d) oxygen (a) sublimation (b) chromatography
® 2-methyl-3- pentanone (a) 1S, 2S (b) 1S, 2R (c) 1R, 2R (d) 1R, 2S (c) crystallization (d) steam distillation
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276 CHEMISTRY Organic Chemistry : Some Basic Principles and Techniques 277

36. Which one of the following is a technique most suitable for 46. Geometrical isomerism is possible in case of : 56. The following compounds differ in 63. Which of the substance is purified by sublimation?
purification of cyclohexanone from a mixture containing (a) pentene-2 (b) propane H Cl H Cl (a) Benzoic acid (b) Camphor
benzoic acid, isoamyl alcohol, cyclohexane an d (c) pentane (d) ethene C=C C=C (c) Naphthalene (d) All of these
cyclohexanone? H Cl Cl H 64. The most reactive compound for electrophilic nitration is
47. The number of isomers of the compound with molecular
(a) Crystallization (b) Sublimation (a) configuration (b) conformation (a) Benzene (b) Nitrobenzene
formula C2H2Br2 is (c) structure (d) chirality
(c) IR spectroscopy (d) Gas chromatography (a) 4 (b) 3 (c) 5 (d) 2 (c) Benzoic acid (d) Toluene.
37. Which of the following is optically active ? 57. A mixture of methyl alcohol and acetone can be separated 65. Which of the following molecules is achiral?
48. One among the following will show optical activity? by
H H NH2 H O
H H (a) distillation
(a) C C CH3
(a) CH 3 C C C2 H5 (b) CH3 — CHOH — CH3 H C C (b) fractional distillation
CH(Cl)CH3 (a) CH2CH3 (b) H
H (c) steam distillation
OH OH (d) distillation under reduced pressure H OH
Br CH3 H 58. The correct statement about the compounds (A), (B) and CH3
(b) C C CH(CH3)2 OH
C C (C) is :
H Cl SH
(c) CH3 C C COOH (d) CH3 CH2 C= O CH3 H Cl SH
COOCH 3 COOH COOH (c) (d)
O Br OH H3C CHCl2 H OH H OH H OH
38. The correct stability order of following species is – (c) C C CH3 66. Which one of the following is a free-radical substitution
H C C H OH H OH HO H
H3C reaction?
CH3 COOCH 3
COOH COOCH 3
(C) (a) CH 3CHO + HCN ¾
¾® CH 3CH ( OH ) CN
(x) (y) H3C (A) (B)
CH2Cl CH CH
(d) C C 2 3 (a) (A) and (B) are identical CH3 CH2Cl
C C C (b) Boiling
H (b) (A) and (B) are diastereomers +Cl2
(z) (w) H CH2Cl2
(c) (A) and (C) are enantiomers
(a) x > y > w > z (b) y > x > w > z 49. The number of ether isomers possible for C4H10O are : (d) (A) and (B) are enantiomers CH3
Anh. AlCl3
(c) x > w > z > y (d) z > x > y > w (a) 2 (b) 5 (c) 4 (d) 3 59. Which compound on nitration will give highest amount of (c) +CH3Cl
39. An aromatic compound of formula C7H7Cl has in all ..... 50. Keto-enol tautomerism is observed in : m-substituted product ?
isomers :
O O CH3 CH2–Cl CH2Cl CH2NO2
(a) 5 (d) 2 (c) 4 (d) 3 (d)
40. How many optically active stereoisomers are possible for || || + AgNO2
(a) H 5 C 6 - C - CH 2 - C - C 6 H 5
lactic acid ? (a) (b) 67. Which of the following undergoes nucleophilic substitution
(a) 1 (b) 2 (c) 4 (d) 3
O exclusively by SN1 mechanism?
41. The correct IUPAC name for || Cl (a) Ethyl chloride (b) Isopropyl chloride
(b) H 5 C 6 - C - CH 3 Cl
CH C Cl (c) Chlorobenzene (d) Benzyl chloride
Cl Cl 68. Styrene can be purified by
O
|| (a) Simple distillation (b) Fractional distilation
(c) (d)
(c) H 5C 6 - C - H (c) Steam distillation (d) Vacuum distillation
69. The correct order regarding the electronegativity of hybrid
(a) 5-methyl -4-(1'-2'-demethylpropyl) heptane (d) Both (a) and (b) 60. The molecular formula of diphenyl methane, orbitals of carbon is
(b) 3-methyl-4-(1',2'-dimethylpropyl) heptane 51. The best method for the separation of naphthalene and (a) sp > sp2 > sp3 (b) sp < sp2 > sp3
CH2 , is C13H12.
(c) 2,3,5-trimethyl-4-propylheptane benzoic acid from their mixture is: (c) sp < sp2 < sp3 (d) sp > sp2 < sp3
(d) 4-propyl-2,3,5-trimethylpeptane (a) distillation (b) sublimation How many structural isomers are possible when one of the 70. The example of an electrophilic substitution reaction is :
42. Geometrical isomerism is possible in : (c) chromatography (d) crystallisation hydrogens is replaced by a chlorine atom? NH2 N(C2H 5)2
(a) CH 3CH(CH 3 )CH 2 CH 2 CH 3 52. Isomerism due to rotation around C–C single bond is : (a) 6 (b) 4 (c) 8 (d) 7 (a) +C2H5B r®
(a) Enantiomerism (b) Position isomerism 61. Nitroethane can exhibit one of the following kind of
(b) CH 3CH = CHCH 3 isomerism:
(c) Conformation (d) Diastereoisomerism
(a) metamerism (b) optical activity (b) OH + X– N2+ SO3– Na+
(c) CH 3 CH = CH 2 53. If a compound has n asymmetric carbon atoms, then maximum
number of optical isomers are given by the formula (c) tautomerism (d) position isomerism
(d) ClH 2 C - CH 2 Cl 62. Tautomerism is exhibited by – ® Na O
+ –
N=N SO3- Na +
n
43. How many acyclic structural isomers are possible for the æ 1ö
(a) 2n (b) ç ÷ (c) 2n (d) 2 n
compound with molecular formula C3H3Cl3 ? è 2ø (1) CH = CH – OH (2) O O (c) H 2C
HBr
= CH – CH 3 ¾¾¾¾®
(a) 3 (b) 2 (c) 5 (d) 6 54. Which is a chiral molecule? Peroxide

44. The number of optical enantiomorphs of tartaric acid is/are: (a) 2, 2-dimethylbutanoic acid Br – CH 2 – CH 2 – CH3
(a) 1 (b) 4 (c) 3 (d) 2 (b) 4-methylpentanoic acid O
(3) O (4) O
45. Which of the cations in more stable ? (c) 3-methylpentanoic acid ||
NuH
H (d) 3,3-dimethylbutanoic acid (d) H 2C = CH - C - CH3 ¾¾¾ ®
H 55. In Kjeldahl’s method, CuSO4 acts as O O
| | + O
(a) R '- C + - OR (b) R '- C = OR (a) oxidising agent (b) reducing agent (a) (1), (3) and (4) (b) (2), (3), and (4) ||
(c) hydrolysing agent (d) catalytic agent (c) All of these (d) None of these NuCH2 CH 2 - C - CH3
(c) both equal (d) both are unstable
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278 CHEMISTRY Organic Chemistry : Some Basic Principles and Techniques 279

71. Which one of the following does not have sp2 hybridized 84. Which of the following pairs represent electrophiles? (a) (C), (B), (A), (D) (b) (B), (C), (A), (D) 103. How many stereoisomers does this molecule have ?
carbon ? (a) AlCl3, H2O (b) SO3, NO2+ (c) (D), (C), (B), (A) (d) (A), (B), (C), (D) CH3CH = CHCH 2CHBrCH 3
(a) Acetonitrile (b) Acetic acid (c) BF3, H2O (d) NH3, SO3 94. 1,2-Dihydroxybutane has the formula
(a) 4 (b) 6 (c) 8 (d) 2
(c) Acetone (d) Acetamide 85. Chromatography is a valuable method for the separation, (a) C(OH) – C(OH) – C – C (b) C – C(OH)2 – C – C
104. The stability of carbanions in the following :
72. Rate of the reaction isolation, purification and identification of the constituents (c) (OH)C – C – C – C(OH) (d) C – C(OH) – C(OH) – C
O O – of a mixture and it is based on general principle of 95. Which of the following represents the correct order of
R – C + Nu R – C + Z is fastest when Z is (a) phase rule (b) phase distribution stability of the given carbocations ? (I) RC = C (II)
Z Nu (c) interphase separation (d) phase operation
+ |+ + + |+ +
(a) OC2H5 (b) NH2 (c) C l (d) OCOCH3 86. The shape of methyl carbanion is similar to that of – (a) F3C > F3C - C > CH3 (b) H3C > F3C - C > F3C (III) R 2C = CH (IV) R 3C - CH 2
73. The increasing order of stability of the following free radicals (a) BF3 (b) NH3 | | is in the order of :
is (c) methyl free radical (d) methyl carbocation (a) (I) > (II) > (III) > (IV) (b) (II) > (III) > (IV) > (I)
• • •
(a) (C6H5)2 C H < (C6H5)3 C < (CH3)3 C < (CH3)2 C H
• 87. The replacement of chlorine of chlorobenzene to give phenol |+ + + |+ + + (c) (IV) > (II) > (III) > (I) (d) (I) > (III) > (II) > (IV)
• • • • requires drastic conditions, but the chlorine of (c) F3C - C > F3C > H3C (d) F3C - C > H3C > F3C 105. In the hydrocarbon
(b) (CH3)2 C H < (CH3)3 C < (C6H5)2 C H < (C6H5)3C 2,4-dinitrochlorobenzene is readily replaced since, | |
• • • • CH3 – CH = CH – CH2 – C º CH
(c) (CH3)2 C H < (CH3)3 C < (C6H5)2 C H < (C6H5)3 C (a) nitro groups make the aromatic ring electron rich at 96. A bottle containing two immiscible liquids is given to you.
• • ortho/para positions 6 5 4 3 2 1
• •
(d) (C6H5)3C < (C6H5)2 C H < (CH3)3 C < (CH3)2 C H They may be separated by using a
The state of hybrization of carbons 1, 3 and 5 are in the
(b) nitro groups withdraw electrons from the meta position (a) Fractionating column (b) Separating funnel
74. Steam distillation is used for the purification of : following sequence :
of the aromatic ring (c) Vacuum distillation (d) Steam distillation
(a) covalent compounds (a) sp2, sp, sp3 (b) sp, sp3, sp2
(c) nitro groups donate electrons at meta position 97. Distillation is used to separate liquids which differ in the b.p
(b) electrovalent compounds (c) sp, sp2, sp3 (d) sp3, sp2, sp
(d) nitro groups withdraw electrons from ortho/para by
(c) co-ordinate compounds 106. The state of hybridization of C2, C3, C5 and C6 of the
positions of the aromatic ring (a) 5°C (b) 10°C
(d) volatile compounds hydrocarbon,
88. The optical inactivity due to internal compensation can be (c) 30 – 80°C (d) 100°C
75. Which of the following is strongest nucleophile – CH3 CH3
exhibited by : 98. Example of chain isomerism are :
(a) Br– (b) : OH– | |
(a) dextro-tartaric acid (b) laevo-tartaric acid (a) Ortho and meta toluic acids CH3 C CH = CH CH C º CH
(c) : CN - (d) C2 H 5O : (c) racemic-tartaric acid (d) meso-tartaric acid (b) Methyl acetate and ethyl formate 7 6| 5 4 3 2 1
76. Strongest acid among the following is : 89. Consider the following phenols : (c) Pentanoic acid and 2-methyl butanoic acid CH3
(a) CCl 3COOH (b) CH 3COOH OH OH OH OH (d) 2-pentanone and 3-pentanone is in the following sequence:
99. CH3 – CHCl – CH2 – CH3 has a chiral centre. which one of (a) sp3, sp2, sp2 and sp (b) sp, sp2, sp2 and sp3
(c) CF3 COOH (d) CBr3 COOH the following represents its R-configuration? (c) sp, sp2, sp3 and sp2 (d) sp, sp3, sp2 and sp3
77. The prussian blue colour obtained in the Lassaigne’s test C2 H 5 C2 H5 107. Which of the following compounds will exhibit cis-trans
for nitrogen is due to the formation of NO2 | | (geometrical) isomerism?
(a) Iron (II) hexacyanoferrate (III) CH3 NO2 (a) H - C - CH3 (b) Cl - C - CH3 (a) Butanol (b) 2-Butyne
(b) Iron (III) hexacyanoferrate (II) I II III IV | | (c) 2-Butenol (d) 2-Butene
(c) Iron (III) hexacyanoferrate (III) The decreasing order of acidity of the above phenols is Cl H 108. Cyclohexanol (I), acetic acid (II), 2, 4, 6-trinitrophenol (III)
(d) Iron (II) hexacyanoferrate (II) (a) III > IV > II > I (b) II > I > IV > III and phenol (IV) are given. In these the order of decreasing
(c) I > IV > II > III (d) III > IV > I > II CH3 C2 H 5
78. Which one of the following species is isoelectronic with | | acidic character will be :
90. Absolute alcohol cannot be obtained by simple fractional
ammonia ? (c) H - C - Cl (d) H3C - C - Cl (a) III > II > IV > I (b) II > III > I > IV
distillation because | | (c) II > III > IV > I (d) III > IV > II > I
(a) CH -2 (b) +CH2 (c) –CH3 (d) +CH3 (a) Pure C2H5OH is unstable C2 H5 H 109. The correct order of increasing reactivity of C – X bond
79. A meta-directing functional group is : (b) C2H5OH form hydrogen bonds with water 100. For (i) I– , (ii) Cl– , (iii) Br – , the increasing order of towards nucleophile in the following compounds is:
(a) — COOH (b) OH (c) Boiling point of C2H5OH is very close to that of water nucleophilicity would be X X
(c) — CH3 (d) — Br (d) Constant boiling azeotropic mixture is formed with water (a) Cl– < Br– < I– (b) I– < Cl– < Br– NO2
80. The following compound will undergo electrophilic 91. Impure glycerine can be purified by (c) Br– < Cl– < I– (d) I– < Br– < Cl–
(a) Steam distillation (b) Simple distillation (CH3)3 C – X, (CH3)2CH – X
substitution more readily than benzene : 101. The order of decreasing reactivity towards an electrophilic
(a) Nitrobenzene (b) Benzoic acid (c) Vacuum distillation (d) Extraction with a solvent reagent, for the following would be
(c) Benzaldehyde (d) Phenol 92. Consider the acidity of the carboxylic acids : (i) benzene (ii) toluene NO2
81. In Kjeldahl’s method for the estimation of nitrogen, the (A) PhCOOH (B) o-NO2C6H4COOH (iii) chlorobenzene (iv) phenol (I) (II) (III) (IV)
foumula used is (C) p-NO2C6H4COOH (D) m-NO2C6H4COOH (a) (ii) > (iv) > (i) > (iii) (b) (iv) > (iii) > (ii) > (i) (a) I < II < IV < III (b) II < III < I < IV
Which of the following order is correct ? (c) (iv) > (ii) > (i) > (iii) (d) (i) > (ii) > (iii) > (iv) (c) IV < III < I < II (d) III < II < I < IV
1.4VW
(a) %N = (b) %N = 1.4VW (a) B > D > A > C (b) B > D > C > A 102. Which one of the following is most reactive towards 110. Among the given compounds, the most susceptible to
N V (c) A > B > C > D (d) B > C > D > A
VNW 1.4 VN electrophilic attack ? nucleophilic attack at the carbonyl group is:
(c) %N = (d) %N = 93. The decreasing order of nucleophilicity among the
W CH2OH (a) CH 3COOCH3 (b) CH 3CONH 2
1.8 nucleophiles
82. The number of s and p bonds in a molecule of acetonitrile (b) CH 3 COOCOCH 3 (d) CH3COCl
are respectively (A) CH 3C - O - (B) CH 3 O - (a) (b)
|| 111. The correct IUPAC name of the compound
(a) 2, 5 (b) 3, 4 (c) 4, 3 (d) 5, 2
O
83. An asymmetric carbon atom is that in which : (C) CN - Cl
(a) three similar and one dissimilar groups O is
OH
(b) two similar and two dissimilar groups ||
(c) all the different groups (D) H C
3 S – O – is (c) (d)
(d) none of the above ||
O
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280 CHEMISTRY Organic Chemistry : Some Basic Principles and Techniques 281

(a) 4-Ethyl-3-propyl hex-1-ene 117. The alkene that exhibits geometrical isomerism is : 8. Among the following compounds (I - III), the ease of their 17. Which of the following is the strongest base ?
(b) 3-Ethyl-4-ethenyl heptane (a) 2- methyl propene (b) 2-butene reaction with electrophiles is,
(c) 3-Ethyl-4-propyl hex-1-ene (c) 2- methyl -2- butene (d) propene OCH3 NO2 (a) (b) NHCH3
(d) 3-(1-ethylpropyl) hex-1-ene 118. The number of stereoisomers possible for a compound of
112. The IUPAC name of the following compound is the molecular formula
Cl CH2CH3 CH3 – CH = CH – CH(OH) – Me is:
(b) 2 (c) 4 (d) 6 (d) 3 (c) NH2 (d) CH2NH2
C C
119. Out of the following, the alkene that exhibits optical isomerism is I II III
18. Which type of isomerism is possible in the compound
CH3 I (a) 3-methyl-2-pentene (b) 4-methyl-1-pentene (a) II > III > I (b) III > II > I
(c) 3-methyl-1-pentene (d) 2-methyl-2-pentene (c) II > I > III (d) I > II > III
COOH
(a) trans-2-chloro-3-iodo-2-pentene
(b) cis-3-iodo-4-chloro-3-pentene 120. The IUPAC name of the following compound is OH 9. Which one of the following compounds is resistant to ?
(c) trans-3-iodo-4-chloro-3-pentene (a) 4-Bromo-3-cyanophenol nucleophilic attack by hydroxyl ions ? (a) Geometrical (b) Optical
(d) cis-2-chloro-3-iodo-2-pentene (a) Methyl acetate (b) Acetonitrile (c) Both (d) None
(b) 2-Bromo-5-hydroxybenzonitrile
(c) Diethyl ether (d) Acetamide 19. Which pair of isomerism is not possible together?
113. The IUPAC name of is (c) 2- Cyano-4-hydroxybromobenzene CN 10. Which one of the following orders is correct regarding the (a) Ring-chain and functional
(d) 6-Bromo-3-hydroxybenzonitrile Br –I effect of the substituents ? (b) Geometrical and optical
(a) 3-ethyl-4, 4-dimethylheptane 121. Hyperconjugation involves overlap of the following orbitals (a) —NR2 <—OR >—F (b) —NR2 > —OR >—F (c) Metamerism and functional
(b) 1, 1-diethyl-2,2-dimethylpentane (c) —NR2 <—OR <—F (d) —NR2 >—OR <—F (d) Metamerism and chain
(c) 4, 4-dimethyl-5,5-diethylpentane (a) s-s (b) s - p (c) p- p (d) p-p
11. Which of the following is false regarding a good contributor
(d) 5, 5-diethyl-4,4-dimethylpentane. 122. In allene (C3H4), the type(s) of hybridisation of the carbon 20. CH 3 Br + Nu - ¾¾® CH 3 - Nu + Br -
of a resonance hybrid?
114. Presence of a nitro group in a benzene ring atoms is (are) : (a) It must have as many bonds as possible The decreasing order of the rate of the above reaction with
(a) deactivates the ring towards electrophilic substitution (a) sp and sp3 (b) sp and sp2 (b) It must have as many octets as possible nucleophiles (Nu–) A to D is
(b) activates the ring towards electrophilic substitution (c) Negative charge, if any, should be on electronegative [Nu– = (A) PhO–, (B) AcO–, (C) HO–, (D) CH3O–]
(c) renders the ring basic (c) only sp3 (d) sp2 and sp3
atom (a) A > B > C > D (b) B > D > C > A
(d) deactivates the ring towards nucleophilic substitution. 123. Which one of the following conformations of cyclohexane (c) D > C > A > B (d) D > C > B > A
115. The correct decreasing order of priority for the functional (d) None of the three
is chiral? 12. Correct order of stability is : 21. Lassaigne’s test is used to detect
groups of organic compounds in the IUPAC system of
(a) Boat (b) Twist boat (c) Rigid (d) Chair. (a) cis -2- butene > 1-butene > trans -2-butene (a) nitrogen and halogens (b) sodium and halogens
nomenclature is
(a) – COOH, – SO3H, – CONH2, – CHO 124. Directing influence of the methyl group can be explained on (b) trans-2-butene > cis-2-butene > 1-butene (c) halogens and sulphur (d) All of these
(b) – SO3H, – COOH,– CONH2, – CHO the basis of (c) 1-butene > cis-2-butene > trans-2- butene 22. The reason for the loss of optical activity of lactic acid when
(c) – CHO, – COOH, – SO3H, – CONH2 (a) inductive effect (b) electromeric effect (d) cis-2-butene > trans-2-butene > 1-butene OH group is changed by H is that :
(d) – CONH2, – CHO, – SO3H, – COOH (c) resonance effect (d) no-bond resonance 13. The correct order of reactivity towards the electrophilic (a) Chiral centre of the molecule is destroyed
116. The IUPAC name of neopentane is 125. The number of isomers of the compound C 2 BrFCl is substitution of the compounds aniline (I), benzene (II) and (b) Molecule acquires asymmetry
(a) 2, 2 dimethylpropane (b) 2 methylpropane nitrobenzene (III) is (c) Due to change in configuration
(a) 3 (b) 4 (c) 5 (d) 6
(c) 2, 2 dimethylbutane (d) 2- methylbutane (a) I > II > III (b) III > II > I (d) Structural change occurs
(c) II > III > I (d) I < II > III 23. Which of the following does not exhibit cis-trans isomerism?
14. Which of the following is least reactive in a nucleophilic (a) C 6 H 5CH = NOH (b) C 6 H 5 N = NC 6 H 5
substitution reaction. (c) (d) None of the three
(a) (CH 3 )3 C - Cl (b) CH 2 = CHCl 24. C – H bond energy is about 101 kcal/mol for methane, ethane
(c) CH 3CH 2Cl (d) CH 2 = CHCH 2 Cl and other alkanes but is only 77 kcal/mol for C – H bond of
1. Which of the following is true? (a) 3-pentanone, cyclopentanone, n-pentanal CH3 in toluene. This is because :
(a) A cis isomer has lower b.p. than the trans (b) n-pentanal, 3-pentanone, cyclopentanone 15. Which of the following is true regarding hyperconjugation,
(a) of inductive effect due to – CH3 in toluene
(b) A cis isomer has lower m.p. than the tans (c) n-pentanal, cyclopentanone, 3-pentanone also known as no-bond resonance?
(b) of the presence of benzene ring in toluene.
(c) All isomers of nitrophenols are equal soluble in water (d) cyclopentanone, 3-pentanone, n-pentanal (i) Like inductive effect it involves donation of electrons
(c) of resonance among the structures of benzyl radical in
(d) All the three are correct 6. The reaction : through s bonds
toluene
2. Which is weakest base : (CH2)5CH3 (ii) Hyperconjugation involves overlapping of filled
CH3 (CH2 )5 H H (d) of aromaticity of toluene
(a) C6H5 – CH2 – NH2 (b) C6H5 – CH2 – NH – CH3 orbitals with the empty p orbital of the carbocation
C – Br OH
HO – C (iii) Like resonance, it involves displacement of p or lone 25. In Carius method 0.099 g organic compound gave 0.287 g
(c) O2N – CH2 – NH2 (d) CH3 – NH – CHO
CH3 pair of electrons to the carbon bearing positive charge AgCl. The percentage of chlorine in the compound will be
3. Which of the following is maximum stable H3C
(a) Conjugated alkadiene (CH2 = CH – CH = CH2) (iv) It involves delocalisation of s and p- electrons (a) 28.6 (b) 71.7 (c) 35.4 (d) 64.2
is described as 26. Select the appropriate relation with respect to acidity of X, Y,
(b) Isolated alkadiene (CH2 = CH – CH2 – CH = CH2) (a) (ii) and (iv) (b) (ii)
(c) Cumulated alkadiene (CH2 = C = CH2) (a) S (b) S (c) S (d) S (c) (iii) (d) none Z for the given compound, with increasing order.
E2 N1 N0 N2
(d) All are equal 7. Which of the following is not correct? 16. In the anion HCOO– the two carbon-oxygen bonds are found + +
4. Which is true regarding the relative basic character of the Order of basicity Order of nucleophilicity to be of equal length. what is the reason for it ? H3N NH3
following two pairs? Z X
(a) The C = O bond is weaker than the C — O bond
(a) NH3 > NH2OH (b) –CCl3 > –CF3
(a) F - > Cl - > Br - Br - > Cl - > F - COOH
(b) The anion HCOO– has two resonating structures
(c) Both are true (d) Nither is true (b) - - - - (c) The anion is obtained by removal of a proton from the Y
H - O - O > OH H - O - O > OH
5. Decreasing order of reactivity towards nucleophilic addition acid molecule (a) Z > X > Y (b) Y > Z > X
to carbonyl group among cyclopentanone, 3-pentanone and (c) - CH 3 > NH -2 > OH - - CH 3 > NH 2- > OH - (d) Electronic orbitals of carbon atom are hybridised (c) Z < X > Y (d) X > Y > Z
n-pentanal is (d) H2O > H2S H2O < H2S
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282 CHEMISTRY Organic Chemistry : Some Basic Principles and Techniques 283

27. The shape of transition state is – COOH (ii) 38. Which of the following compounds undergoes nucleophilic (c) (CH3 )3 C > (CH3 )2 CH > C6 H5 CH 2 > C Cl3
R substitution reaction most easily ? (d) C6 H5 CH 2 > C Cl3 > (CH3 )3 C > (CH3 ) 2 CH
Nu– + H C X [Transition state] Cl 43. The correct order of increasing basicity of the given
Cl conjugate bases (R = CH3) is
R
R (a) (b) (a) RCOO < HC º C < R < NH 2
NO2
–––––® Nu C H + X– NO2 (b) R < HC º C < RCOO < NH 2
OH CH3 (c) RCOO < NH 2 < HC º C < R
R (iii)
(a) Triangular planar (b) Square pyramidal Cl (d) RCOO < HC º C < NH 2 < R
HO
(c) Trigonal bipyramidal (d) Tetrahedral Cl 44. Among the following, the least stable resonance structure
(i)
28. Arrange the following alcohols in order of their decreasing (c) (d) is
(iv)
tendency to form carbocation. Å O
(a) (ii) > (i) > (iii) > (iv) (b) (ii) > (iii) > (i) > (iv) Å
(c) (i) > (ii) > (iii) > (iv) (d) (ii) > (iv) > (i) > (iii) OCH3 (a)
N
OH 33. Which of the following is most stable? 39. Which of the following molecules is expected to rotate the
+ plane of plane-polarised light? O
F OH F +
COOH
O
CH 3 (a) (b) Å
O O (a) H2N (b)
I II H Å N
OH H3C CH 3 + H O
H2C + CHO
C 6 H 5 CH 2 OH
(c) (d) O
CH 3 OH O (b) HO (c) Å
O H
Å N
III IV
34. Sodium nitroprusside, when added to an alkaline solution of
(a) I > II > III > IV (b) IV > III > I > II (c) CH2OH O
sulphide ions, produces purple colour ion due to the
IV > III > II > I (d) II > I > IV > III formation of (c)
29. Which molecule will be most reactive for SN1 reaction – (a) Na[Fe(H2O)5 NOS] (b) Na2[Fe(H2O)5 NOS] O
Cl Å
(c) Na3[Fe(CN)5NOS] (d) Na4[Fe(CN)5NOS] SH
H2N NH2 (d)
Å N
CH3 CH3 35. Base strength of :
(a) (b) Br – , (B) (d) H H O
(A) H 3CCH 2
H 2C = CH and (C) H - C º C
Ph Ph 45. The number of stereoisomers obtained by bromination of
CH3 is in the order of : 40. The absolute configuration of
CH3 (a) (B) > (A) > (C) (b) (C) > (B) > (A) trans-2-butene is
(c) (A) > (C) > (B) (d) (A) > (B) > (C) HO2C CO2H (a) 1 (b) 2 (c) 3 (d) 4
Cl CH3 36. Which one of the following is most reactive towards
46. The correct stability order for the following species is
(c)
CH3 (d) I electrophilic reagent ? OH
CH3 HO H H
CH3 CH3 + + +
(a) (b) (a) S, S (b) R, R (b) R, S (c) S, R O O
30. Diazo compounds, sometimes do not respond Lassaigne’s +
test for nitrogen because OCH3 OH 41. The electrophile, E Å attacks the benzene ring to generate (I) (II) (III) (IV)
(a) these are quite stable compounds and do not CH3 CH3 the intermediate s-complex. Of the following, which s- (a) (II) > (IV) > (I) > (III) (b) (I) > (II) > (III) > (IV)
decompose to elemental nitrogen
(b) these contain very little carbon (c) (d) complex is lowest energy? (c) (II) > (I) > (IV) > (III) (d) (I) > (III) > (II) > (IV)
(c) these form organometallic compounds with sodium NHCOCH3 CH2OH NO2 47. In the following carbocation, H/CH3 that is most likely to
(d) their nitrogen contents is removed, during heating, in 37. Which one is a nucleophilic substitution reaction among H migrate to the positively charged carbon is
the form of nitrogen gas the following ? + E
(a) (b) +
(a) CH3 – CH = CH2 + H2O CH3 – CH – CH3 H H
31. — X + Nu ¾¾
® — Nu + X , OH
H E 1 2 + 4 5
NO2 NO2 H3C — C —3C — C — CH3
(b) RCHO + R¢ MgX R – CH – R¢ H
the reaction is not possible because –
(a) Nu faces steric hinderance on attacking the leaving OH (c) + E (d) + H HO H CH3
CH3
group E
(b) electrons are delocalised in the benzene ring (c) CH3 – CH2–CH–CH2Br + NH3 42. Arrange the carbanions, (a) CH3 at C-4 (b) H at C-4
(c) reaction is thermodynamically controlled CH3 (CH3 )3 C , C Cl3 , (CH3 ) 2 CH , C6 H5 CH 2 (c) CH3 at C-2 (d) H at C-2
(d) C – X bond possesses a double bond character in order of their decreasing stability :
CH 3–CH2–CH–CH2NH2
32. Which of the following represent the decreasing order of Ka (a) (CH3 ) 2 C H > C Cl3 > C6 H5 C H2 > (CH3 )3 C
(d) CH3CHO + HCN ¾¾
® CH3CH (OH) CN
values? (b) C Cl3 > C6 H5 CH 2 > (CH 3 )2 CH > (CH3 )3 C
EBD_7753

284 CHEMISTRY Organic Chemistry : Some Basic Principles and Techniques 285

DIRECTIONS for Qs. 48 to 50 : These are Assertion-Reason 48. Statement-1 : Aniline is better nucleophile than anilium ion. 12. Ionic species are stabilised by the dispersal of charge. Which 17. Some meta-directing substituents in aromatic substitution
type questions. Each of these question contains two statements: Statement-2 : Anilium ion have +ve charge. of the following carboxylate ion is the most stable? are given. Which one is most deactivating? [2013]
Statement-1 (Assertion) and Statement-2 (Reason). Answer O O (a) –SO3H (b) –COOH
49. Statement-1 : Trans-2-butene on reaction with Br2 gives || || (c) –NO2 (d) –C º N
these questions from the following four options. meso-2, 3-dibromobutane. (a) CH3 - C - O - (b) Cl - CH 2 - C - O -
18. Which of the following compounds will not undergo Friedal-
(a) Statement-1 is true, Statement-2 is true, Statement-2 is a Statement-2 : The reaction involves syn-addition of bromine. O O Craft’s reaction easily : [2013]
correct explanation for Statement-1 || F ||
(a) Xylene (b) Nitrobenzene
50. Statement-1 : Different number of electron pairs are present (c) F - CH 2 - C - O- CH - C - O-
(d)
(b) Statement-1 is True, Statement-2 is True ; Statement-2 is NOT in resonance structures. F (c) Toluene (d) Cumene
13. Electrophilic addition reactions proceed in two steps. The 19. The structure of isobutyl group in an organic compound is :
a correct explanation for Statement-1 Statement-2 : Resonance structures differ in the location of first step involves the addition of an electrophile. Name the
(c) Statement-1 is True, Statement-2 is False (a) CH3 - CH - CH 2 - CH3 [2013]
electrons around the constituent atoms. type of intermediate formed in the first step of the following ½
(d) Statement-1 is False, Statement-2 is True addition reaction. H3C – HC = CH2 + H+ ----® ? (b) CH3 - CH 2 - CH2 - CH 2 -
(a) 2° carbanion (b) 1° carbocation CH3
(c) 2° carbocation (d) 1° carbanion |
14. Covalent bond can undergo fission in two different ways. (c) CH3 - C-
|
The correct representation involving a heterolytic fission of CH3
CH3 – Br is CH 3
(a) Å (d) CH - CH 2 -
CH 3 - Br ¾ ¾
® CH 3 + Br
Exemplar Questions These are generally insoluble in water at room temperature CH 3
r
1. Which of the following is the correct IUPAC name? but are miscible with water vapour in vapour phase. A suitable (b) ® CH 3 + Br s
CH 3 - Br ¾ ¾ 20. Arrange the following in increasing order of stability
(a) 3-ethyl-4, 4-dimethylheptane method for the extraction of these oils from the flowers is [NEET Kar. 2013]
r
(b) 4, 4-dimethyl-3-ethylheptane (a) distillation (c) ® CH 3 + Br s
CH 3 - Br ¾ ¾ Å Å
(b) crystallisation (A) (CH3 )2 C - CH2CH3 (B) (CH3 )3 - C
(c) 5-ethyl-4, 4-dimethylheptane (d) r s
(d) 4, 4-bis(methyl)-3-ethylheptane (c) distillation under reduced pressure CH3 - Br ¾ ¾ ® CH 3 + Br Å Å
(d) steam distillation 15. The addition of HCl to an alkene proceeds in two steps. The (C) (CH3 )2 - CH (D) CH3 - CH 2
O O
|| || 7. During hearing of a court case, the judge suspected that Å
2. The IUPAC name for CH3 - C - CH 2 - CH 2 - C - OH is first step is the attack of H+ ion to C—
—C portion (E) CH 3
some changes in the documents had been carried out. He
asked the forensic department to check the ink used at two which can be shown as (a) E < D < C < B < A (b) E < D < C < A < B
(a) 1-hydroxypentane-1, 4-dione (c) D < E < C < A < B (d) A < E < D < C < B
(b) 1, 4-dioxopentanol different places. According to you which technique can give
(a) + 21. Given
(c) 1-carboxybutan-3-one the best results? H C—
—C
(d) 4-oxopentanoic acid (a) Column chromatography Br H
H Br
3. The IUPAC name for (b) Solvent extraction (b) + CH3 Br
(c) Distillation H C—
—C H
Cl
(d) Thin layer chromatography CH3 and
NO2 (c) H
+
C——C H CH3 CH3
8. The principle involved in paper chromatography is
Br
(a) adsorption (b) partition (d) All of these are possible
(c) solubility (d) volatility
NEET/AIPMT (2013-2017) Questions I II
9. What is the correct order of decreasing stability of the
following cations? 16. Structure of the compound whose IUPAC name is 3-ethyl-2- I and II are [NEET Kar. 2013]
CH3
hydroxy-4-methylhex-3-en-5-ynoic acid is : [2013] (a) A pair of optical isomers
(a) 1-chloro-2-nitro-4-methylbenzene Å Å
I. CH3 - C H - CH3 II. CH3 - C H - OCH3 OH (b) Identical
(b) 1-chloro-4-methyl-2-nitrobenzene (c) A pair of conformers
(c) 2-chloro-1-nitro-5-methylbenzene Å (d) A pair of geometrical isomers
(a) COOH
(d) m-nitro-p-chlorotoluene III. CH3 - C H - CH 2 - OCH3 22. Homolytic fission of the following alkanes forms free radicals
4. Electronegativity of carbon atoms depends upon their state (a) II > I > III (b) II > III > I CH3 – CH3, CH3 – CH2 – CH3, (CH3)2 CH – CH3, CH3 – CH2
of hybridisation. In which of the following compounds, the OH
(c) III > I > II (d) I > II > III – CH (CH3)2. Increasing order of stability of the radicals is
carbon marked with asterisk is most electronegative? COOH
10. Correct IUPAC name for H3C – CH – CH – CH3 is ......... . (b) [NEET Kar. 2013]
(a) CH3 – CH2 – *CH2 – CH3 g g
| | (a) (CH3)3 C < (CH3)2 C – CH2CH3 <
(b) CH3 – *CH = CH – CH3
C2H5 C2H5 g g
(c) CH3 – CH2 – C º *CH CH3 – C H – CH3 < CH3 – C H2
(d) CH3 – CH2 – CH = *CH2 (a) 2-ethyl-3-methylpentane g g g
COOH (b) (CH3)2 C – CH2CH3 < CH3 – C H – CH3 < CH3 – C H2
5. In which of the following functional groups, isomerism is (b) 3, 4-dimethylhexane (c) g
(c) 2-sec-butylbutane < (CH3)3 C
not possible? OH g g
(a) Alcohols (b) Aldehydes (d) 2, 3-dimethylbutane OH (c) CH3 – C H2 < CH3 – C H – CH3 <
11. In which of the following compounds the carbon marked g g
(c) Alkyl halides (d) Cyanides (CH3)2 C – CH2 – CH3 < (CH3)3 C
6. The fragrance of flowers is due to the presence of some with asterisk is expected to have greatest positive charge? g g g
(a) *CH3 — CH2 — Cl (b) *CH3 — CH2 — Mg+Cl– (d) COOH (d) CH3 – C H2 < CH3 – C H – CH3 < (CH3)3 C < (CH3)2
steam volatile organic compounds called essential oils. g
(c) *CH3 — CH2 — Br (d) *CH3 — CH2 — CH3 C – CH2CH3
 EBD_7
286 CHEMISTRY Organic Chemistry : Some Basic Principles and Techniques 287

23. What is the hybridisation state of benzyl carbonium 30. Consider the following compounds [2015] 35. The correct statement regarding the comparison of 37. The IUPAC name of the compound [2017]
+ CH3 Ph staggered and eclipsed conformation of ethane, is [2016] O O
ion —CH2? [NEET Kar. 2013] || ||
(a) The staggered conformation of ethane is less stable H–C
CH3—C—CH— Ph—C—PH
(a) sp3 (b) sp2 CH3 than eclipsed conformation, because staggered
conformation has torsional strain is :-
(c) spd2 (d) sp2 d CH3
24. Nitrogen detection in an organic compound is carried out (I) (II) (III) (b) The eclipsed conformation of ethane is more stable
by Lassaigne’s test. The blue colour formed corresponds to Hyperconjugation occurs in : than staggered conformation, because eclipsed (a) 5-formylhex-2-en-3-one
which of the following formulae? [NEET Kar. 2013] (a) II only (b) III only conformation has no torsional strain (b) 5-methyl-4-oxohex-2-en-5-al
(a) Fe3[Fe(CN)6]3 (b) Fe3[Fe(CN)6]2 (c) The eclipsed conformation of ethane is more stable (c) 3-keto-2-methylhex-5-enal
(c) I and III (d) I only
(c) Fe4[Fe(CN)6]3 (d) Fe4[Fe(CN)6]2 than staggered conformation even though the eclipsed (d) 3-keto-2-methylhex-4-enal
31. Which of the following is the most correct electron 38. The correct statement regarding electrophile is:- [2017]
25. Which of the following compounds will undergo racemisation conformation has torsional strain
displacement for a nucleophilic reaction to take place?
when solution of KOH hydrolyses? [2014] (a) Electrophile is a negatively charged species and can
[2015] (d) The staggered conformation of ethane is more stable form a bond by accepting a pair of electrons from another
CH2Cl
than eclipsed conformation, because staggered electrophile
H H2
(i) (a) H3C—C = C – C – Cl conformation has no torsional strain. (b) Electrophiles are generally neutral species and can form
H a bond by accepting a pair of electrons from a
(ii) CH3CH2CH2Cl 36. The most suitable method of separation of 1 : 1 mixture of
H H2
(b) H 3C—C = C – C – Cl ortho and para-nitrophenols is : [2017] nucleophile
CH3 H (a) Chromatography (c) Electrophile can be either neutral or positively charged
| H H2 species and can form a bond by accepting a pair of
(iii) H3C - C H - CH2Cl (c) H 3C—C = C – C – Cl (b) Crystallisation
H electrons from a nucleophile
CH3 H H2 (c) Steam distillation (d) Electrophile is a negatively charged species and can
(d) H 3C—C = C – C – Cl (d) Sublimation form a bond by accepting a pair of electrons from a
C H nucleophile
(iv) H Cl 32. In Duma's method for estimation of nitrogen, 0.25 g of an
C2H3 organic compound gave 40 mL of nitrogen collected at 300
(a) (i) and (ii) (b) (ii) and (iv) K temperature and 725 mm pressure. If the aqueous tension
(c) (iii) and (iv) (d) (i) and (iv) at 300 K is 25 mm, the percentage of nitrogen in the compound
26. In the Kjeldahl’s method for estimation of nitrogen present is : [2015]
in a soil sample, ammonia evolved from 0.75 g of sample (a) 18.20 (b) 16.76
neutralized 10 mL of 1 M H2SO4. The percentage of nitrogen
(c) 15.76 (d) 17.36
in the soil is : [2014]
(a) 37.33 (b) 45.33 33. The pair of electron in the given carbanion, CH3C º C- , is
(c) 35.33 (d) 43.33
present in which of the following orbitals ? [2016]
27. Two possible stereo-structures of CH3CHOH.COOH, which
(a) 2p (b) sp3
are optically active, are called. [2015 RS]
(c) sp2 (d) sp
(a) Diastereomers (b) Atropisomers
34. Which of the following biphenyls is optically active ?
(c) Enantiomers (d) Mesomers
[2016]
28. Which of the following statements is not correct for a
(a) O2N
nucleophile? [2015 RS]
(a) Nucleophile is a Lewis acid
(b) Ammonia is a nucleophile
I
(c) Nucleophiles attack low e– density sites Br Br
(d) Nucleophiles are not electron seeking.
29. Given (b)
CH3 CH3 CH I I
3
I
CH3 CH3
(c)
CH3
O O O I
(I) (II) (III) CH3
Which of the given compounds can exhibit tautomerism?
(a) I and III (b) II and III [2015] (d)
(c) I, II and III (d) I and II CH3