1048 General Organic Chemistry

32. Which of the following species is paramagnetic in nature (c) RCOOH (d) HCl
1 [NCERT 1984] 45. Which gives monosubstituted product [DPMT 2005]
(a) Free radical (b) Carbonium ion 14 (a) o -dinitrobenzene (b) m -dinitrobenzene
(c) Carbanion (d) All the above
(c) p -dinitrobenzene (d) Nitrobenzene
33. In which of the following species the central C-atom is negatively
2 charged [NCERT 1985] 46. An aromatic compounds among other things should have a  -
(a) Carbanion (b) Carbonium ion 15 electron cloud containing electrons where n can't be
(c) Carbocation (d) Free radical [J & K 2005]
34. Which of the following free radicals is most stable (a) 1/2 (b) 3
[NCERT 1982] (c) 2 (d) 1
3 (a) Primary (b) Methyl 47. Which of the following is an electrophile [J & K 2005]
(c) Secondary (d) Tertiary 16 (a) H 2 O (b) SO 3
35. Which of the following contains three pairs of electrons
[BHU 1985]
(c) NH 3 (d) ROR
4
(a) Carbocation (b) Carbanion 48. The presence of the chlorine atom on benzene ring makes the
(c) Free radical (d) None of these 17 second substituent enter at a position [J & K 2005]
36. Which of the following carbanion is most stable (a) ortho (b) meta
5 [NCERT 1983] (c) para (d) ortholpara
(a) Methyl (b) Primary 49. Which is the most stable carbocation [J & K 2005]
(c) Secondary (d) Tertiary 18 (a) iso-propyl (b) Triphenylmethyl cation
37. Among the given cations, the most stable carbonium ion is (c) Ethyl cation (d)  -propyl cation
6 [IIT-JEE 1981]
(a) sec-butyl (b) ter-butyl
(c) n-butyl (d) None of these Organic reactions and their mechanism
38. In the compound given below
  1. To which of the following four types does this reaction belong
7 HN NH
B  R  A  B  R  A
3 3

(Y) (Z ) [Manipal MEE 1995]

19 (a) Unimolecular electrophilic substitution
(b) Bimolecular electrophilic substitution
COOH
(c) Unimolecular nucleophilic substitution
(X) of the acidity of the positions (X), (Y) and (Z) is
The correct order [IIT-JEE Screening 2004] substitution
(d) Bimolecular nucleophilic
(a) (Z) > (X) > (Y) (b) (X) > (Y) > (Z) 2. An alkyl halide may be converted into an alcohol by
(c) (X) > (Z) > (Y) (d) (Y) > (X) > (Z) 20 [Pb. PMT 2000]
39. C-C bond length in benzene is (a) Elimination (b) Addition
[MP PMT 1987; MP PMT 2001; AIIMS 2001] (c) Substitution (d) Dehydrohalogenation
8 (a) 1.39 Å 3. CH 3 CH 2  Cl
(b) 1.54 Å
21
(c) 1.34 Å
(d) Different in different bonds
The above reaction proceeds through [AMU 2000]
40. Heterolysis of carbon-chlorine bond produces
(a) Nucleophilic substitution
9 [MNR 1986; MP PET/PMT 1998]
(b) Electrophilic substitution
(a) Two free radicals
(c) Free radical substitution
(b) Two carbonium ions
(d) More than one of the above processes
(c) Two carbanions
(d) One cation and one anion 4. Geometry of reaction intermediate in SN 1 reaction is
[MH CET 2001]
41. In CH 3 CH 2 OH, the bond that undergoes heterolytic cleavage 22 (a) Tetrahedral (b) Planar
most readily is [IIT-JEE 1988]
10 (c) Triangular bipyramidal (d) None of these
(a) C – C (b) C – O
(c) C – H (d) O – H CH 3 CH 3
| |
42. Which of the following intermediate have the complete octet around 5. H 3 C  C  Br  KOH ( Aq.)  H 3 C  C  OH  KBr
the carbon atom [Orissa JEE 2003] | |
11 23 CH 3 CH 3
(a) Carbonium ion (b) Carbanion ion
(c) Free radical (d) Carbene above reaction is [RPMT 2003]
1 2
43. A solution of D (+) - 2-chloro-2-phenylethane in toluene racemises (a) SN (b) SN
12 slowly in the presence of small amount of SbCl 5 , due to the (c) E1 (d) Both (a) and (b)
formation of [IIT-JEE 1999]
6. In electrophilic substitution reaction nitrobenzene is
(a) Carbanion (b) Carbene [Kerala (Med.) 2003]
(c) Free radical (d) Carbocation 24
(a) Meta-directing
44. The reagent in Friedel Craft's reaction is [DPMT 2005] (b) Ortho-directing
13 (a) Pyridine (b) RCOCl (c) Para-directing
 General Organic Chemistry 1049
(d) Not reactive and does not undergo any substitution (b) Benzyl bromide hydrolysis
(e) Non-selective (c) Reaction of NaOH with dinitrofluorobenzene
7. The most common type of reaction in aromatic compounds is [Orissa JEE 2003] (d) Sulphonation of benzene
(a) Elimination reaction 20. Which is an electrophile [DCE 2000]
25 38 
(b) Addition reaction (a) AlCl3 (b) CN
(c) Electrophilic substitution reaction (c) NH 3 (d) CH 3 OH
(d) Rearrangement reaction
21. Strongest nucleophile is [BHU 2003]
8. The function of AlCl3 in Friedel-Craft’s reaction is (a) RNH 2 (b) ROH
39
26 [KCET 2003]
(a) To absorb HCl (b) To absorb water (c) C6 H 5 O  (d) CH 3 O 
(c) To produce nucleophile (d) To produce electrophile 22. The major product obtained when Br2 / Fe is treated with
9. Which of the following can’t be used in Friedal Craft’s reactions[AFMC 2004] O
27 40 HN
(a) FeCl 3 (b) FeBr2 is
HC CH
(c) AlCl3 (d) NaCl 3 3

[IIT-JEE Screening 2004]

10. The nitration of a compound is due to the [Pb. PMT 2004] O O
28 (a) NO 2 (b) NO 3 HN HN
(c) NO (d) NO 2 (a)
HC
3
CH 3

(b)
HC
3
CH 3

11. Dehydrohalogenation of an alkyl halide is a/an

[MH CET 2004]
(a) Nucleophilic substitution reaction Br Br O
29 O
(b) Elimination reaction HN HN
(c) Both nucleophilic substitution and elimination reaction
HC CH HC CH
(d) Rearrangement
3 3

(c) (d)
3 3

12. Addition of HCl to vinyl chloride gives 1, 1-dichloroethane because of[MP PET 2004]
30 (a) Mesomeric effect of Cl 23. WhichBrone of the following is least reactive in a nucleophilicBr
(b) Inductive effect of Cl substitution reaction [CBSE PMT 2004]
41 (a) CH 3 CH 2 Cl (b) CH 2  CHCH 2 Cl
(c) Restricted rotation around double bond
(d) None of these (c) (CH 3 )3 C  Cl (d) CH 2  CHCl
13. Formation of ethylene from acetylene is an example of 24. Among the following the strongest nucleophile is
(a) Elimination reaction (b) Substitution reaction [AIIMS 2005]
31 (c) Addition reaction (d) Condensation reaction 42 (a) 
C2 H 5 SH (b) CH 3 COO
14. Conversion of CH 4 to CH 3 Cl is an example of which of the
following reaction [Pb. CET 2001] (c) CH 3 NH 2 (d) NCCH 2
32
(a) Electrophilic substitution 25. The reaction [AIEEE 2005]
(b) Free radical addition 43 O O
 
(c) Nucleophilic substitution RC  Nu  R  C  X , is fastest when X
(d) Free radical substituion
X Nu
15. Following reaction, (CH 3 )3 CBr  H 2O  (CH 3 )3 COH  HBr is
33 is an example of (a) Cl (b) NH 2
[DCE 2002]
(a) Elimination reaction (b) Free radical substitution (c) OC2 H 5 (d) OCOR
(c) Nucleophilic substitution (d) Electrophilic substitution 26. Elimination of bromine from 2-bromobutane results in the
16. Which is an electrophile [DCE 2002] formation of [AIEEE 2004, 05]
(a) BCl3 (b) CH 3 OH 44 (a) Equimolar mixture of 1 and 2-butene
34 (b) Predominantly 2-butene
(c) NH 3 (d) AlCl4 (c) Predominantly 1-butene
(d) Predominantly 2-butyne
17. The electrophile in the nitration of benzene is
[Orissa JEE 2004] 27. Examine the following statements pertaining to an SN 2 reaction
35 (1) The rate of reaction is independent of the concentration of the
(a) NO 2 (b) NO 2 45 nucleophile
(c) NO 
(d) NO 2 (2) The nucleophile attacks the C  atom on the side of the
molecule opposite to the group being displaced
18. The following compound will undergo electrophilic substitution (3) The reaction proceeds with simultaneous bond formation and
more readily than benzene [UPSEAT 2004]
36 bond rupture/cleavage
(a) Nitrobenzene (b) Benzoic acid Amongst the following which of the above were true
(c) Benzaldehyde (d) Phenol [NCERT 1982]
19. Which represents nucleophilic aromatic substitution reaction (a) 1, 2 (b) 1, 3
[Orissa JEE 2004] (c) 1, 2, 3 (d) 2, 3
37 (a) Reaction of benzene with Cl in sunlight 28. What is the decreasing order of reactivity amongst the following
2
compounds towards aromatic electrophilic substitution [IIT-JEE 1995]
 1050 General Organic Chemistry
I. Chlorobenzene II. Benzene H H
III. Anilinium chloride IV. Toluene | |
(a) I  II  III  IV (b) IV  II  I  III (a) HO  C  COOH (b) CH 3  C  COOH
(c) II  I  III  IV (d) III  I  II  IV | |
29. Which of the following applies in the reaction, H Cl
alc. KOH
CH 3 CHBrCH 2 CH 3   CH 3 CH 3
47
(i) CH 3 CH  CHCH 3 (major product) | |
(c) CH 3  C  COOH (d) CH 3  C  COOH
(ii) CH 2  CHCH 2 CH 3 (minor product) | |
[Orissa JEE 2005] OH Cl
(a) Markovnikov's rule (b) Saytzeff's rule
(c) Kharasch effect (d) Hofmann's rule 6. In ethane and cyclohexane which one of the following pairs of
30. Bromination of alkanes involves [J & K 2005] conformations are more stable
56 (a) Eclipsed and chair conformations
48 (a) Carbanions (b) Carbocations
(c) Carbenes (d) Free radicals (b) Staggered and chair conformations
31. Which of the following cannot undergo nucleophilic substitution (c) Staggered and boat conformations
under ordinary conditions [J & K 2005] (d) Eclipsed and boat conformations
49 (a) Chlorobenzene (b) tert-butylchloride 7. Which of the following may exist in enantiomorphs
(c) Isopropyl chloride (d) None of these 57 [CBSE PMT 1988]
32. Which of the following alkyl groups has the maximum + I effect[KCET 2002]
50 CH 3
(a) CH 3  (b) (CH 3 )2 CH 
|
(c) (CH 3 )3 C  (d) CH 3CH 2  (a) CH 3  CH  COOH
(b) CH 2  CHCH 2 CH 2 CH 3
Structural and stereo isomerism NH 2
|
1. Only two isomers of monochloro product is possible of (c) CH 3  CH  CH 3
[IIT-JEE 1986]
51 (a) n-butane (b) 2,4-dimethyl pentane NH 2
(c) Benzene (d) 1-methyl propane |
(d) CH 3  CH 2  CH  CH 3
2. Which is the example of branch isomerization
8. Which of the following compounds may not exist as enantiomers [CPMT 1987]
[NCERT 1976]
(a) CH 3 CH (OH )CO 2 H
52 C C 58
| | (b) CH 3 CH 2 CH (CH 3 )CH 2 OH
(a) C  C  C  C – C and C  C  C (c) C 6 H 5 CH 2 CH 3
|
C (d) C 6 H 5 CHClCH 3
C C 9. Number of isomers of molecular formula C 2 H 2 Br2 are
| | [CPMT 1987]
(b) C  C  C and C  C  C 59
| |
(a) 1 (b) 2
C C (c) 3 (d) 0
10. Lactic acid shows which type of isomerism
C 60 [CPMT 1987; MP PMT 1987; BHU 2003]
C | (a) Geometrical isomerism (b) Tautomerism
(c) C  C  C and C  C  C (c) Optical isomerism (d) Metamerism
C |
C 11. Which one of the following is an optically active compound
[CBSE PMT 1988; DPMT 1983]
61
(d) C  C  C  C and C  C  C (a) n-propanol (b) 2-chlorobutane
| (c) n-butanol (d) 4-hydroxyheptane
C 12. Compounds with same molecular formula but different structural
3. The isomer of diethyl ether is [CPMT 1975] formulae are called [BHU 1979; AFMC 1989]
62 (a) Isomers (b) Isotopes
53 (a) (CH 3 )2 CHOH (b) (CH 3 )3 C  OH
(c) Isobars (d) Isoelectronic
(c) C 3 H 7 OH (d) (C 2 H 5 )2 CHOH 13. Which one of the following compounds shows optical isomerism[MP PET 1990]
4. Isomers have essentially identical (a) CH 3 CHCl  CH 2  CH 3
63
[CBSE PMT 1988; MP PMT 1983, 86] (b) CH 3  CH 2  CHCl  CH 2  CH 3
54 (a) Structural formula (b) Chemical properties
(c) Molecular formula (d) Physical properties (c) ClCH 2  CH 2  CH 2  CH 3
5. Which one of the following shows optical activity (d) ClCH 2  CH 2  CH 3
55 [NCERT 1984, 90] 14. Which one of the following objects is ‘achiral’
64 (a) Letter P (b) Letter F
(c) Ball (d) A pair of hand
15. Total number of isomers of a disubstituted benzene compound is
65 (a) 1 (b) 2
 General Organic Chemistry 1051
(c) 3 (d) 4 H H C2 H H
16. Separating of d and l enantiomorphs from a racemic mixture is (a) CC (b) C C
called [CBSE PMT 1988; DPMT 1983; H3C CH 3 H H
66 KCET 2002] CH 3
(a) Resolution (b) Dehydration CH 3 H | H
(c) Rotation (d) Dehydrohalogenation (c) CC (d) H  C  C  C
CH 3 H | | H
17. Number of optical isomers of lactic acid are H H
67 (a) 1 (b) 2 75
(c) 3 (d) 4 25. Maximum number of isomers of alkene C 4 H 8 are
18. Which one of the following contains asymmetric carbon atom[IIT-JEE 1989; Roorkee 2000] [IIT-JEE 1982; MP PMT 1985; MADT Bihar 1995;
Kerala (Engg.) 2002]
Cl Br H Cl (a) 2 (b) 3
68
| | | | (c) 4 (d) 6
(a) H C CH (b) H C  C  Cl 26. Rotation of plane polarised light is measured by
| | | | 76 [CPMT 1985; DCE 2001]
H H H H (a) Manometer (b) Polarimeter
(c) Viscometer (d) Refractometer
H H H H 27. An alkane forms isomers if the number of least carbon atom is[CPMT 1976; BHU 19
| | | | 77 (a) 1 (b) 2
(c) H C  C H (d) H C  C  CH 3
(c) 3 (d) 4
| | | |
28. Which is not found in alkenes [AIIMS 1982; RPMT 1999]
H H Br OH
78 (a) Chain isomerism (b) Geometrical isomerism
19. n-butane and isobutane are examples of (c) Metamerism (d) Position isomerism
69 (a) Chain isomers (b) Geometrical isomers 29. How many isomers of C 5 H 11 OH will be primary alcohols
(c) Position isomers (d) Tautomers 79 [CBSE PMT 1992]
(a) 2 (b) 3
20. Which of the following has chiral structure
(c) 4 (d) 5
70 CH 3
30. The compound C 4 H 10 O can show
|
(a) CH 3  CH  CH 2 COOH 80 [IIT-JEE 1981; MP PET 2000]
(a) Metamerism (b) Functional isomerism
(b) CH 3  CH  CH  CH 3 (c) Positional isomerism (d) All types
CH 3 31. The number of possible alcoholic isomers for C 4 H 10 O are
| [DPMT 1984; MNR 1986]
(c) CH 3  CH  CH 2 OH
81
(a) 4 (b) 2
(d) CH 3  CHOH  CH 2 CH 3 (c) 3 (d) 5
21. Which of the following pairs is an example of position isomerism 32. How many isomers are possible for C 4 H 8 O

71 (a) CH 3  CH 2  CH 2  CH 3 and CH 3  CH  CH 3 82 [MNR 1992; UPSEAT 2001, 02]

| (a) 3 (b) 4
CH 3 (c) 5 (d) 6
(b) CH 3  CH 2  CH  CH 2 and CH 3  CH  CH  CH 3 33. Which of the following can exhibit cis-trans isomerism
[CBSE PMT 1989]
CH 3  CH 2 OH and CH 3  O  CH 3 83
(c) (a) HC  CH (b) ClCH = CHCl
CH 3 (c) CH 3 .CHCl .COOH (d) ClCH 2  CH 2 Cl
| 34. The number of geometrical isomers in case of a compound with the
(d) CH 3  C  CH 3 and CH 3  CH 2  CH 2  CH 2  CH 3 structure CH 3  CH  CH  CH  CH  C 2 H 5 is
| 84
CH 3 [NCERT 1980]
(a) 4 (b) 3
22. Geometrical isomerism is shown by
[IIT-JEE 1983; CPMT 1990, 94; CBSE PMT 1992;
(c) 2 (d) 5
72 35. The property by virtue of which a compound can turn the plane
MP PET 1997; AMU (Engg.) 1999]
85 polarised light is known as [BHU 1979]
(a) 2-butene (b) 2-butyne
(a) Photolysis (b) Phosphorescence
(c) 2-butanol (d) Butanal
(c) Optical activity (d) Polarization
23. An organic compound exhibits optical isomerism when
36. Meso-tartaric acid is optically inactive due to the presence of
[CPMT 1971, 78, 81; MP PET 1999]
73 (a) Four groups linked to carbon atom are different 86 [AIIMS 1982; MP PMT 1987]
(a) Molecular symmetry
(b) Three groups linked to carbon atom are different
(c) Two groups linked to carbon atom are different (b) Molecular asymmetry
(d) All the groups linked to carbon atom are same (c) External compensation
24. Which one of the following exhibits geometrical isomerism (d) Two asymmetric C-atoms
[NCERT 1979; DPMT 1984; CBSE PMT 1990] 37. Which of the following compounds exhibits optical isomerism[BHU 1983; AFMC 199
74 87
 1052 General Organic Chemistry
MP PMT 1999, 2000] (b) Butanone and butanal
(a) CH 3 CH 2 COOH (b) CH 3 CHOHCOOH (c) Ethoxy propane and propoxy ethane
(d) Methoxy methane and ethanol
(c) CH 3 CH 2 CH 2 OH (d) CH 3 CHOHCH 3
50. Functional isomerism is exhibited by the following pair of
38. The maximum number of stereoisomers possible for 2-hydroxy-2- compounds
methyl butanoic acid is [Roorkee 1992] 100 (a) Acetone, propionaldehyde
88
(a) 1 (b) 2 (b) Diethyl ether, methyl propyl ether
(c) 3 (d) 4 (c) Butane, isobutane
39. Which one of the following pairs represents the stereoisomerism[AIIMS 1992] (d) 1-butene, 2-butene
89 (a) Geometrical isomerism, position isomerism 51. The total number of possible isomeric trimethyl benzene is
(b) Geometrical isomerism, conformational isomerism 101 [MP PET 1997]
(c) Optical isomerism, geometrical isomerism (a) 2 (b) 3
(d) Optical isomerism, metamerism (c) 4 (d) 6
40. Diethyl ether is not associated with which one of these isomers [AFMC 1993]52. Optically active isomers but not mirror images are called
90 (a) Butanoic acid (b) Methyl propionate [MP PET 1999]
(c) Steroisomerism (d) None of these
102 (a) Enantiomers (b) Mesomers
41. Diethyl ether and methyl n-propyl ether are (c) Tautomers (d) Diastereoisomers
91 [MP PET 1994; AFMC 1999; MP PMT 2002] 53. C 7 H 9 N has how many isomeric forms that contain a benzene
(a) Position isomers (b) Functional isomers ring [CPMT 1997, 99; JIPMER 2002; DCE 2003]
103
(c) Metamers (d) Chain isomers (a) 4 (b) 5
42. n-propyl alcohol and isopropyl alcohol are examples of (c) 6 (d) 7
[MP PMT 1994]
92 54. The total number of isomers formed by C 5 H 10 is
(a) Position isomerism (b) Chain isomerism
(c) Tautomerism (d) Geometrical isomerism 104 [Bihar MEE 1996]
43. It is possible to distinguish between optical isomers by (a) 2 (b) 3
93 [Manipal MEE 1995; AFMC 1995] (c) 4 (d) 5
(a) Infrared spectroscopy (e) None of these
(b) Mass spectrometry 55. Which of the following contains asymmetric centre
105 [CPMT 1996]
(c) Melting point determination
(a) 2-butene (b) 2, 2-dimethylpropane
(d) Polarimetry
(c) 2-hexyne (d) Lactic acid
44. The isomerism exhibited by alkyl cyanide and alkyl isocyanide is[AFMC 1995, 97]
56. Which of the following cannot be given to exemplify chiral structure[JIPMER 1997]
94 (a) Functional (b) Positional
106 (a) A shoe (b) A screw
(c) Tautomerism (d) Metamerism
(c) A screw driver (d) All of these
45. The following compound can exhibits
57. Which of the following is expected to be optically active
95 CH 3 H 107 [JIPMER 1997]
CC H [IIT-JEE 1995; DCE 2000]
CH 3 C (a) (CH 3 )4 C (b) C 2 H 5 CH (CH 3 )C 3 H 7
CH 3 COOH (c) (C 2 H 5 )2 CHCH 3 (d) CH 3 CH  CHCH 3
(a) Tautomerism 58. Which compound does not show geometrical isomerism
(b) Optical isomerism [RPMT 1997]
(c) Geometrical isomerism 108 (a) 2-butene (b) 2-pentene
(d) Geometrical and optical isomerisms (c) 2,3-dibromo-2-butene (d) 2-methyl propene
46. Name the compound, that is not isomer with diethyl ether 59. The isomers which can be converted into another forms by rotation
96 [IIT-JEE 1981; CPMT 1989; MADT Bihar 1995] of the molecules around single bond are
(a) n-propylmethyl ether
109
[AIIMS 1997]
(b) Butane-1-ol (a) Geometrical isomers (b) Conformers
(c) 2-methylpropane-2-ol (c) Enantiomers (d) Diastereomers
(d) Butanone 60. The number of enantiomers of the compound
47. Which statement is true for cyclohexane [MP PET 1996] 110 CH 3 CHBrCHBrCOOH is [AIIMS 1997]
97 (a) It has two possible isomers (a) 0 (b) 1
(b) It has three conformations (c) 3 (d) 4
(c) Boat conformation is most stable
61. C 6 H 5 C  N and C 6 H 5 N  C exhibit which type of isomerism[CPMT 1997]
(d) Chair and boat conformations differ in energy by 44 kJ/mol
111 (a) Position (b) Functional
48. Two compounds have the structural formulae
98 CH 3  O  CH 2 CH 3 and CH 3  CH 2  CH 2 OH . The (c) Dextro isomerism (d) Metamerism
62. Which of the following compounds is not chiral
above is an example of
112 [CBSE PMT 1998; DPMT 2002]
(a) Metamerism (b) Functional isomerism
(a) DCH 2 CH 2 CH 2 Cl (b) CH 3 CH 2 CHDCl
(c) Positional isomerism (d) Chain isomerism
49. Which of the following pairs are not isomeric compounds (c) CH 3 CHDCH 2 CH 2 Cl (d) CH 2 CHClCH 2 D
(a) Ethyl ethanoate and methyl propanoate 63. cis and trans 2-butene are [BHU 1998; DPMT 2002]
99