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Organic Chem Mcqs PDF
Organic Chem Mcqs PDF
H
H H H 8 7 6 5 4 3
H H (iv) CH3 CH CH 2 CH 2 CH 2 CH CH 2 CH 2 CH3
| |
C C CH3 CH 2 CH3
(b) H C C C 2 1
C (a) (i) and (ii) (b) (iv) only
H
H
(c) (i), (ii) and (iv) (d) (ii) only
H 18. The correct decreasing order of priority of functional
H H
H
H H
H H
groups is
H C C
(a) – SO3H , – OH, – COCl, C=C
C
(c) C C
(b) – COOH, – SO3H, – COOR, – OH
C (c) – C C, – NH2, – OH, C=O
H H H H (d) – CN, – CONH2, C = O, – OH
H H H H 19. Which of the following is incorrectly matched –
H C C
H
(a) vinegar carboxylic acid
C C C (b) C2H6 alkane
(d) (c) ethanol alcohol
C
(d) methanol ketone
H H H H
20. The functional group present in organic, acid is –
14. Structural formula of benzene is (a) – OH (b) – CHO
H H (c) –COOH (d) > C = O
H C H 21. Which of these contains the carbonyl group?
C H C C H
H C C H H H (a) ketones (b) aldehydes
(a) H (b) H C C H (c) esters (d) all of these
C C H C
H C 22. Butanone is a four-carbon compound with the functional
H H group –
H
H (a) carboxylic acid (b) aldehyde.
C C H (c) ketone (d) alcohol.
H C C H 23. The functional group present in CH3COOC2H5 is –
H C C H
(c) H C C H (d) H C C H (a) ketonic (b) aldehydic
C H (c) ester (d) carboxylic
C
H H 24. Which of the following compounds contains 1°, 2°, 3° as
15. The successive members in a homologues series differ well as 4° carbon atoms ?
from each other by ________ (a) Neopentane (b) 2-methyl pentane
(a) – CH2CH2– unit (b) – CH2 unit (c) 2,3-dimethyl butane (d) 2,2,3-trimethyl pentane
(c) – OCH3 unit (d) – CH3 unit 25. The number of secondary hydrogens in 2, 2-dimethylbutane
is
16. Which of the following have incorrect molecular formula?
(a) 8 (b) 6
A. Icosane – C10H22
(c) 4 (d) 2
B. Triacontane – C30H62
26. The compound which has one isopropyl group is
C. Nonane – C9H20 (a) 2, 2, 3, 3 - Tetramethylpentane
D. Heptane – C7H14 (b) 2, 2 - Dimethylpentane
(a) (A) and (D) (b) Only (D) (c) 2, 2, 3- Trimethylpentane
(c) (B) and (D) (d) Only (B) (d) 2- Methypentane
17. Which of the following are incorrect methods of selecting 27. Which of the following statements is false for isopentane ?
parent chain ? (a) It has three CH3 groups
1 2 3 4 5 6 (b) It has one CH2 group
(i) CH3 CH CH 2 CH 2 CH 2 CH CH 2 CH 2 CH3 (c) It has one CH group
| |
CH3 7CH 2 CH 3 (d) It has a carbon which is not bonded to hydrogen
8
ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES & TECHNIQUES 183
28. The number of primary, secondary and tertiary carbons in 3, (a) 3-bromo-1-chlorocyclohexene
4-dimethylheptane are respectively (b) 1-bromo-3-chlorocyclohexene
(a) 4, 3 and 2 (b) 2, 3 and 4 (c) 2-bromo-6-chlorocyclohex-1-ene
(c) 4, 2 and 3 (d) 3, 4 and 2 (d) 6-bromo-2-chlorocyclohexene
29. The number of primary, secondary, tertiary and quaternary 37. Name of the following compound is
carbons in neopentane are respectively
CH 3CH 2 CH 3
(a) 4, 3, 2 and 1 (b) 5, 0, 0 and 1
C
(c) 4, 0, 0 and 1 (d) 4, 0, 1 and 1 CH 3 CH 2 OH
30. What is the IUPAC name of t-butyl alcohol.
(a) Butanol–2 (b) 2–Methyl-propan–2-ol (a) 2-ethylbutan-2-ol
(c) Butanol–1 (d) Propanol-2 (b) 1-ethyl-1-methylpropan-1-ol
31. The IUPAC name of CH3COCH (CH3)2 is - (c) 3-methyl pentan-3-ol
(a) isopropyl methyl ketone (d) diethylethanol
(b) 2-methyl-3-butanone 38. The IUPAC name for
(c) 4-methylisopropyl ketone C1
(d) 3-methyl-2-butanone |
CH3 C CH 2 CH CH CH3 is
32. CH3CH2– CH CH – CH 2CH3 has the IUPAC name – |
| | H
CH3 CHO (a) 5–chlorohex–2–ene
(b) 2–chlorohex–5–ene
(a) 2–sec butylbutanal
(c) 1–chloro–1–methylpent–3–ene
(b) 2, 3–diethylbutanal
(d) 5–chloro–5–methylpent–2–ene
(c) 2–ethyl–3–methylpentanal
39. IUPAC name of following compound is :
(d) 3–methyl–2–ethylpentanal
33. Which of the following statements is false for isopentane– H
(a) It has three CH3 groups CH
CH33 - C - CH
CH22- -CH
CH
3
(b) It has one CH2 group
(c) It has one CH group
(d) It has a carbon which is not bonded to hydrogen (a) 2 - cyclohexylbutane (b) 2 - phenylbutane
34. The IUPAC name of the compound (c) 3 - cyclohexylbutane (d) 3 - phenylbutane
CH 3OCH 2 CH 2 CH 2 OCH 2 CH 3 is 40. What is the IUPAC name of the following compound ?
(a) 3-ethoxy-1-methoxypropane NH 2
(b) 1-ethoxy-3-methoxypropane
(c) 2, 5-dioxyhexane
(d) ethoxypropane oxymethane
(a) 2-methyl-4-hexanamine
35. Which of the following compounds has wrong IUPAC
(b) 5-methyl-3-hexanamine
name?
(c) 2-methyl-4-amino hexane
(a) CH3–CH2–CH2 –COO–CH2CH3 ethyl butanoate
(d) 5-methyl-3-amino hexane
(b) CH 3 CH CH 2 CHO 3-methyl-butanal 41. Which one of the following is ethyl-4-(dimethyl amino)
| butanoate ?
CH3
O
|| (b)
OEt
(d) CH3 CH C CH2 CH3 2-methyl-3-pentanone
| NH 2
CH3
36. The IUPAC name of the compound shown below is
(c) H2N
Cl OEt
Br (d) Me 2 N
OEt
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184 ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES & TECHNIQUES
42. Identify the correct IUPAC name of the compound given 49. The IUPAC name of neopentane is
below (a) 2, 2-dimethylpropane (b) 2-methylpropane
(c) 2, 2-dimethylbutane (d) 2-methylbutane
50. The IUPAC name for
H Cl
NO2
O (c) (d)
CH2– C – OH
OH
187. The IUPAC name of compound C is: OCH3 NO2
COOH
CH2– COOH
194. Which one of the following is a free-radical substitution
reaction?
(a) 1, 2, 3 - tricarboxy - 2, 1 - propane
(b) 3 - carboxy - 3 hydroxy - 1 , 5 - pentanedioic acid (a) CH 3CHO HCN CH 3CH ( OH ) CN
(c) 3 - hydroxy - 3 - carboxy - 1, 5 - pentanedioic acid
(d) 2 - hydroxy propane -1, 2, 3 - tricarboxylic acid. CH3 CH2Cl
(b) +Cl2
Boiling
197. Which of the following is least reactive in a nucleophilic 200. The most suitable method for separtion of a 1 : 1 mixture of ortho
substitution reaction. and para nitrophenols is
(a) Sublimation (b) Chromatography
(a) (CH 3 )3 C Cl
(c) Crystallization (d) Steam distillation
(b) CH 2 CHCl 201. The Lassaigne’s extract is boiled with dil. HNO3 before
testing for halogens because
(c) CH 3CH 2Cl (a) silver halides are soluble in HNO3
(b) Na2S and NaCN are decomposed by HNO3
(d) CH 2 CHCH 2 Cl
(c) Ag2S is soluble in HNO3
198. Which of the following does not represent formation of
(d) AgCN is soluble is HNO3
reactive intermediate correctly ?
202. The molecular mass of an organic compound which contains
only one nitrogen atom can be
(i) CH3 CN C H3 CN
(a) 152 (b) 146
(c) 76 (d) 73
(ii) CH 3 C u CH3 Cu 203. 0.25 g of an organic compound on Kjeldahl's analysis gave
enough ammonia to just neutralize 10cm3 of 0.5 M H2SO4.
(iii) CH 3 B r CH3 Br The percentage of nitrogen in the compound is
(a) 28 (b) 56
(iv) CH 3 Cl CH3 Cl (c) 14 (d) 112
204. During hearing of a court case, the judge suspected that
(a) (ii) only (b) (ii) and (iii)
some changes in the documents had been carried out. He
(c) (ii) and (iv) (d) (iii) and (iv) asked the forensic department to check the ink used at two
199. In Lassaigne’s test, the organic compound is fused with a different places. According to you which technique can
piece of sodium metal in order to give the best results?
(a) increase the ionisation of the compound (a) Column chromatography
(b) decrease the melting point of the compound (b) Solvent extraction
(c) increase the reactivity of the compound (c) Distillation
(d) convert the covalent compound into a mixture of ionic (d) Thin layer chromatography
compounds
ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES & TECHNIQUES 195
7. (c) Hybridisation on the particular carbon can be Thus number of secondary hydrogens is two.
established by number of and bonds attached to it. CH3 CH3
Bond Bond Hybridisation | |
4 – sp3 26. (d) CH 3 C C CH 2 CH 3
| |
3 1 sp2 CH3 CH3
2 2 sp
(a )
1 2 3 4
C H2 CH CH C H2 CH3
3 3 3 3 |
1 1 1 1 CH 3 – C – CH 2 CH 3
|
sp 2 sp 2 sp 2 sp 2 CH3
Both carbon atoms forming C—C single bond (C2 and ( b)
C3) are sp2 hybridised
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196 ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES & TECHNIQUES
CH3 CH3 Cl
1 | 3
| | CH3 — C — CH3
2
43. (c)
CH 3 C C HCH 2 CH 3 |
| CH3
CH3
2-chloro-2-methyl propane
(c )
44. (a)
39. (b) The compound is a derivative of butane. o-Chlorotoluene m-Chlorotoluene p-Chlorotoluene benzyl chloride
40. (b) The compound contains longest chain of 6C atoms 54. (b) Alcohols and ethers are functional isomers.
and amino group. Hence it is an alkanamine. 55. (b) Structures (a), (c) and (d) have the same molecular
41. (d) The compound is an ester. Its IUPAC name is derived formula (C6H12O) while (b) has C6H10O as molecular
from alkyl alkanoate. formula
42. (d) The compound is an aldehyde containing longest 56. (d)
chain of 6 C-atoms and side chains.
ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES & TECHNIQUES 197
57. (b) CH3CH2CH2C CH,(CH3)2CHC CH, CH3CH2C CCH3 +
I II III CH2 CH2 CH2 CH2
58. (b) CH3CH2CH=CH2 CH3CH=CHCH3 (CH3)2C=CH2
1-butene (i) 2- butene (ii), (iii) 2-methylpropene
(cis,- trans) (iv)
CH3
Resonating structures of benzyl carbocation
R 120°
CH 2 CH C H 2 CH 2 CH CH 2
Resonating structures of allyl carbocation
R
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198 ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES & TECHNIQUES
83. (c) 103. (c) Resonance effect is the polarity produced in the
84. (a) On exposure to UV light, Cl2 molecule undergoes molecule by the interactions of two – bonds or
homolytic fission, to form chlorine free radicals. between a – bond and a lone pair of electrons
U.V. . present on an adjacent atom.
Cl Cl 2Cl 104. (b) Electromeric effect is purely a temporary effect and is
(Chlorine free radicals) brought into play only at the requirement of attacking
85. (b) The order of stability of free radicals reagent, it vanishes out as soon as the attacking
• • • • reagent is removed from reaction mixture.
(C 6 H 5 ) 3 C (C 6 H 5 ) 2 CH (CH 3 ) 3 C (CH 3 ) 2 C H
105. (b)
The stabilisation of first two is due to resonance and 106. (b) Alkyl groups with at least one hydrogen atom on the
last two is due to inductive effect. -carbon atom, attached to an unsaturated carbon
86. (d) Free radicals are stabilized by hyperconjugation, thus atom, are able to release electrons in the following
3° free radicals having maximum number of way.
hyperconjugative structures are the most stable, and
primary free radical the least.
.
87. (b) C6 H5CHCH3 is a 2º benzylic free radical, hence
stabilized most due to resonance. Note that the delocalisation involves and bond
88. (b) Dichlorocarbene, : CCl2 (a carbene) is the electrophile orbitals (or p orbitals in case of free radicals) ; thus it
formed as an intermediate in Reimer-Tiemann reaction. is also known as – conjugation. This type of
89. (d) Order of stability of free radicals is electron release due to the presence of the system
H—C—C = C is known as hyperconjugation
3° > 2° > 1° > C H3 107. (b) The stability of carbocation on the basis of hyper-
90. (c) The strength of nucleophile depends upon the nature conjugation can be explained as hyperconjugation
of alkyl group R on which nucleophile has to attack stabilises the carbocation because electron density
and also on the nature of solvent. The order of strength from the adjacent -bond helps in dispersing the
of nucleophiles follows the order : positive charge.
CN– > I– > C6H5O– > OH– > Br– > Cl–
91. (c) 92. (d)
H H H H H H H H
93. (a) Electrophile is positivly charged or electron deficient | | | | | | | |
species. Lewis acids are electron acceptors that is H C C H C C HC C H C C
| | | | | | |
electron deficient species. H H H
H H H H H
94. (b) Electrophiles are electron deficient or positively
charged species. In general greater the number of alkyl groups attached
95. (d) BF3 and R3C – X are electrophile while (CH3)3N and to a positively charged carbon atom, the greater is the
C2H5O– are nucleophile hyperconjugation interaction and stabilisation of the
96. (b) –CH3 group has +I effect, as number of –CH3 group cation. Thus, we have the following relative stability
increases, the inductive effect increases. of carbocation.
97. (d) Due to – I effect of the – CHO group, oxygen acquires-
CH3
- charge and the terminal carbon acquires + charge. |
CH3 C (CH3 ) 2 CH CH3 CH 2 CH3
CH2 = CH – C = O |
CH3
H
98. (c) All resonating structures should have same number Hence, stability of carbocation is directly proportional
of electron pairs. to number of alkyl group directly attached to
99. (a) The two structures involve only movement of carbocations.
electrons and not of atoms or groups, hence these are 108. (b) Stability order of different alkyl carbocations on the basis
resonating structures. of hyperconjugation is :
100. (b) Only structure (b) has a conjugated system, which is 3° > 2° > 1° > methyl
necessary for resonance. In t-butyl cation, the C-atom bearing the positive charge
101. (c) is attached to three methyl groups therefore it possess
nine -hydrogens. It will give maximum nine
102. (b) – OH shows + R effect while C = O shows – R hyperconjugative structures leading to maximum
effect. stability.