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Assignment on GENERAL ORGANIC CHEMISTRY with answers., Assignments of Organic Chemistry

Information about organic chemistry, including the synthesis of the first organic compound, the number of optical isomers, stereochemistry, free radicals, and hybridization. It also includes questions related to bonding and hybridization in organic compounds. a comprehensive overview of organic chemistry concepts and is useful for students studying this subject.

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General Organic Chemistry 1043
Wohler synthesised the first organic compound
urea in the laboratory.
The number of optical isomers of a compound
depends on its structure and number of asymmetric
carbon atoms present in its molecule.
Stereoisomers that are not mirror images of each
other are called diastereomers.
Order of priority for both asymmetric carbon
atoms using sequence rules is
OH > COOH > CH(OH)COOH > H
The nitration and sulphonation of alkanes
involve free radicals.
Carbenes undergo insertion reactions.
Alkanes usually undergo free radical substitution
when hydrogen is replaced by a halogen. It is
catalysed by benzoyl peroxide (C6H5COO)2.
The polymerisation of alkenes is free radical
addition reaction.
Allyl free radical (CH2 = CH CH2) is more stable
than n-propyl free radical (CH3CH2CH2).
The stability of free radicals is explained on the
basis of hyperconjugation or conjugation.
Propene is more reactive than ethene towards
electrophilic addition reaction due to the formation
of more stable 2° carbocation.
The reactivity of alkyl halides in SN1 is 3°>
2°>1°>methyl while SN2 is methyl > 1°> 2°> 3°.
Polar solvents favour SN1 while non polar
solvents favour SN2 reactions.
Dipole moment of CHCl3 is less than that of
CH2Cl2. This is because in CH2Cl2 all bond moments
reinforce each other while in CHCl3 the bond moment
of one of the Cl opposes the net moment of the other
two.
Low concentration of nucleophiles favour SN1
while high concentration favour SN2.
In SN1 the attack of the nucleophile may be from
either side and so recimization takes place. However,
in SN2 the attack of the nucleophile takes place from
back side. So it leads to inversion of configuration.
Hunsdieker reaction proceeds via free radical
mechanism.
Propene reacts with chlorine at 673 K to form
allyl chloride and the intermediate is allyl free
radical.
Bonding and hybridisation in organic
compounds
1. In methane molecule, the hydrogen atoms around
carbon are arranged as[DPMT 1980; MNR 1981; MP PET 1997, 99]
(a) Square planar (b) Tetrahedral
(c) Triangular (d) Octahedral
2. In carbon tetrachloride, four valence of carbon
are directed to four corners of [CPMT 1973, 77]
(a) Rectangle (b) Square
(c) Tetrahedron (d) None of these
3. In alkene (ethene) number of
2
sp
hybrid carbon
atoms are
(a) 1 (b) 2
(c) 3 (d) 0
4. Each carbon atom in benzene is in the state of
hybridization
[CPMT 1973, 83, 89; MP PMT 199 3;
KCET (Med.) 1999; DCE 2001]
(a)
3
sp
(b)
2
sp
(c)
sp
(d)
ps3
5. Which of the following hybridisation has highest
percentage of s-character [BHU 1986]
(a)
3
sp
(b)
2
sp
(c)
sp
(d) None of these
6. The hybridisation present in
22 HC
is[EAMCET 1993]
(a)
sp
(b)
2
sp
(c)
3
sp
(d)
2
dsp
7. What hybrid orbitals will form the following
compound
[AFMC 1991]
(a)
sp
and
3
sp
(b)
2
sp
and
3
sp
(c)
sp
and
2
sp
(d) Only
3
sp
8. The compound in which carbon uses only its
3
sp
hybrid orbitals for bond formation is [IIT-JEE 1989]
(a)
HCOOH
(b)
CONH 22 )(
(c)
COHCH 33 )(
(d)
CHOCH 33 )(
9. A straight chain hydrocarbon has the molecular
formula
108HC
. The hybridisation for the carbon
atoms from one end of the chain to the other are
pf3
pf4
pf5
pf8
pf9
pfa
pfd
pfe
pff
pf12
pf13
pf14
pf15
pf16
pf17
pf18
pf19
pf1a
pf1b
pf1c
pf1d
pf1e
pf1f
pf20
pf21
pf22
pf23
pf24
pf25
pf26
pf27
pf28

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 Wohler synthesised the first organic compound

urea in the laboratory.

 The number of optical isomers of a compound

depends on its structure and number of asymmetric

carbon atoms present in its molecule.

 Stereoisomers that are not mirror images of each

other are called diastereomers.

 Order of priority for both asymmetric carbon

atoms using sequence rules is

– OH > – COOH > – CH ( OH ) COOH > – H

 The nitration and sulphonation of alkanes

involve free radicals.

 Carbenes undergo insertion reactions.

 Alkanes usually undergo free radical substitution

when hydrogen is replaced by a halogen. It is

catalysed by benzoyl peroxide ( C 6

H

5

COO )

2

 The polymerisation of alkenes is free radical

addition reaction.

 Allyl free radical ( CH 2 = CH – CH 2 ) is more stable

than n - propyl free radical ( CH 3

CH

2

CH

2

 The stability of free radicals is explained on the

basis of hyperconjugation or conjugation.

 Propene is more reactive than ethene towards

electrophilic addition reaction due to the formation

of more stable 2° carbocation.

 The reactivity of alkyl halides in SN

1

is 3°>

2°>1°>methyl while SN

2

is methyl > 1°> 2°> 3°.

 Polar solvents favour SN

1

while non polar

solvents favour SN

2

reactions.

 Dipole moment of CHCl 3 is less than that of

CH 2 Cl 2. This is because in CH 2 Cl 2 all bond moments

reinforce each other while in CHCl 3

the bond moment

of one of the Cl opposes the net moment of the other

two.

 Low concentration of nucleophiles favour SN

1

while high concentration favour SN

2

 In SN

1

the attack of the nucleophile may be from

either side and so recimization takes place. However,

in SN

2

the attack of the nucleophile takes place from

back side. So it leads to inversion of configuration.

 Hunsdieker reaction proceeds via free radical

mechanism.

 Propene reacts with chlorine at 673 K to form

allyl chloride and the intermediate is allyl free

radical.

Bonding and hybridisation in organic

compounds

1. In methane molecule, the hydrogen atoms around

carbon are arranged as [DPMT 1980; MNR 1981; MP PET 1997, 99]

(a) Square planar (b) Tetrahedral

(c) Triangular (d) Octahedral

2. In carbon tetrachloride, four valence of carbon

are directed to four corners of [CPMT 1973, 77]

(a) Rectangle (b) Square

(c) Tetrahedron (d) None of these

3. In alkene (ethene) number of

2

sp

hybrid carbon

atoms are

(a) 1 (b) 2

(c) 3 (d) 0

4. Each carbon atom in benzene is in the state of

hybridization

[CPMT 1973, 83, 89; MP PMT 1993;

KCET (Med.) 1999; DCE 2001]

(a)

3

sp (b)

2

sp

(c) sp (d) s p

3

5. Which of the following hybridisation has highest

percentage of s- character [BHU 1986]

(a)

3

sp (b)

2

sp

(c) sp

(d) None of these

6. The hybridisation present in

2 2

CH is [EAMCET 1993]

(a) sp (b)

2

sp

(c)

3

sp (d)

2

dsp

7. What hybrid orbitals will form the following

compound

3 2 3

H C  CH  CH  CH  CH [AFMC 1991]

(a) sp and

3

sp (b)

2

sp and

3

sp

(c) sp and

2

sp (d) Only

3

sp

8. The compound in which carbon uses only its

3

sp

hybrid orbitals for bond formation is [IIT-JEE 1989]

(a) HCOOH (b) NH CO

2 2

(c) CH COH

3 3

( ) (d) CH CHO

3 3

9. A straight chain hydrocarbon has the molecular

formula

8 10

CH. The hybridisation for the carbon

atoms from one end of the chain to the other are

respectively sp , sp , sp , sp , sp , sp , sp

3 2 2 3 2 2

and sp

The structural formula of the hydrocarbon would

be [CBSE PMT 1992]

(a)

3 2 2

CH  C  C  CH  CH  CH  CH  CH

(b)

3 2 2 2

CH  CH  CH  CH  CH  C  C  CH  CH

(c)

3 2 2

CH  CH  CH  CH  C  C  CH  CH

(d) CHCHCHCHCHCHCCH

3 2

10. Which of the following has a bond formed by

overlap of

3

spsp hybrid orbitals [MNR 1993; UPSEAT 2001, 02]

(a) CHCCH

3

(b)

3 3

CH  CH  CH  CH

(c)

2 2

CH  CH  CH  CH

(d) HCCH

11. The bond between carbon atom (1) and carbon

atom (2) in compound

2

NCCHCH involves

the hybridised carbon as [IIT-JEE 1987; DCE 2000]

(a)

2

sp and

2

sp (b)

3

sp and sp

(c) sp and

2

sp (d) sp and sp

12. Number of  bonds in

CH  CH  CH  CH  C  CH

2

is

[Kurukshetra CEE 1991; KCET 2000]

(a) 2 (b) 3

(c) 4 (d) 5

13. Number of  electrons present in naphthalene is

[AFMC 1991]

(a) 4 (b) 6

(c) 10 (d) 14

14. Number of  electrons in cyclobutadienyl anion

2

4 4

( )

C H is [IIT-JEE 1991]

(a) 2 (b) 4

(c) 6 (d) 8

15. Homolytic fission of C - C bond in ethane gives an

intermediate in which carbon is [IIT-JEE 1992]

(a)

3

sp hybridised (b)

2

sp hybridised

(c) sp hybridised (d) sp d

2

hybridised

16. In the reaction

4

2

3

2

Catalyst

1 2

2

BrCH CH Br

H

Br

C C

H

Br

H

The hybridisation states of carbon atoms 1, 2, 3, 4

are

[MP PET 1994]

(a) 1 and 2 ;

2

sp 3 and 4

3

sp

(b) 1 and 2 ;

2

sp 3 and 4 sp

(c) 1, 2, 3 and 4 sp

(d) 1, 2 ;

3

sp

2

sp

17. In which of the compounds given below is there

more than one kind of hybridisation ( , , )

2 3

spsp sp

for carbon

(i)

3 2 2 3

CHCHCHCH

(ii)

3 3

CH  CH  CH  CH

(iii)

2 2

CH  CH  CH  CH

(iv) HCCH [CBSE PMT 1995]

(a) ( ii ) and ( iv ) (b) ( i ) and ( iv )

(c) ( ii ) and ( iii ) (d) ( ii )

18. Examine the following common chemical

structures to which simple functional groups are

often attached

(i) (ii)

(iii) (iv) 

3 2 2 2

CHCHCH CH

(v)

H

H

H C  C 

2

Which of these systems have essentially planar

geometry

[CBSE PMT 1995]

(a) ( i ) and ( v ) (b) ( ii ) and ( iii )

(c) ( ii ), ( iii ) and ( iv ) (d) ( iv )

19. The structure of di-chloromethane is [MP PMT 1995]

(a) Tetrahedral (b) Trigonal

(c) Linear (d) Hexagonal

20. The numbers of sigma ( ) bonds in 1-butene is

[MP PMT 1995]

(a) 8 (b) 10

(c) 11 (d) 12

21. Which of the following statements is false for

isopentane

[MP PET 1996]

(a) It has three

3

CH groups

(b) It has one

2

CH group

(c) It has one CH group

(d) It has a carbon which is not bonded to

hydrogen

22. The number of  bonds in o- xylene is [MP PET 1996]

(a) 6 (b) 9

(c) 12 (d) 18

23. In benzene the total number of  bonds is [MP PMT 1997]

(a) 3 (b) 6

(c) 9 (d) 12

(a) 1, 2-butadiene (b) 1, 3-butadiene

(c) 1, 3-pentadiene (d) -butylene

45. In which of the following species is the

underlined carbon having

3

sp hybridisation [AIEEE 2002]

(a) CH COOH

3

(b) CH CHOH

3 2

(c)

3 3

CH COCH

(d)

2 3

CH  CH  CH

46. The HCH bond angle in

4

CH is [MP PET 2002]

(a) 109 28 '

o

(b) 107 28 '

o

(c)

o

90 (d)

o

180

47. The hybridisation of carbons of CC

single bond

of

2

HCCCHCH is [RPMT 2002]

(a)

3 3

spsp (b)

2

spsp

(c) spsp

3

(d)

2 3

spsp

48. The shape of ethylene molecule is [AFMC 2002]

(a) Square planar (b) Furan

(c) Trigonal planar (d) Tetrahedral

49. Acetylene molecule has carbon in [Kerala (Engg.) 2002]

(a) sp - hybridisation (b)

2

sp - hybridisation

(c)

3

sp - hybridisation (d) sp d

3

  • hybridisation 50. In the formation of methane molecule, carbon

makes use of

[DPMT 2001; MP PMT 2002]

(a) sp - hybridised orbitals (b)

2

sp - hybridised orbitals

(c)

3

sp - hybridised orbitals (d) Unhybridised orbitals

51. In graphite C- atom is in ....state [CPMT 2002]

(a)

3

sp (b) sp

(c)

2

sp (d) None of these

52. How many -bonds are present in naphthalene

molecule

[RPMT 2002]

(a) 3 (b) 4

(c) 5 (d) 6

53. Hybridisation state of C in diamond is [RPMT 2002]

(a) sp

(b)

2

sp

(c)

3

sp (d) spd

3

54. The number of and bonds present in pent- 4 -

ene, 1-yne is [AIIMS 2002; CPMT 2002]

(a) 10, 3 (b) 3, 10

(c) 4, 9 (d) 9, 4

55. Which one of the following is more acidic [DPMT 2002]

(a) Butane (b) 1 - butene

(c) 1 - butyne (d) 2 - butyne

56. Graphite is soft while diamond is hard because [BHU 2003]

(a) Graphite is in powder form

(b) Diamond has

2

sp hybridization but graphite

has

3

sp hybridization

(c) Graphite is in planar form while diamond is in

tetrahedral form

(d) Graphite is covalent and diamond is ionic

57. Hybridization of 1 and 2 carbon atoms in

2

1 2

2

CH  C  CH [BHU 2003]

(a) sp , sp

(b)

2 2

sp , sp

(c) sp , sp

2

(d)

3 2

sp , sp

58. Hydrogen bonding is maximum in [UPSEAT 2003]

(a) C HOH

2 5

(b)

3 3

CH  O  CH

(c) CH CO

3 2

( ) (d) CH CHO

3

59. How many methyl group are present in 2, 5 -

dimethyl- 4 - ethylheptane [EAMCET 2003]

(a) 2 (b) 3

(c) 4 (d) 5

60. Which one of the following does not have

2

sp

hybridised carbon [AIEEE 2004]

(a) Acetonitrile (b) Acetic acid

(c) Acetone (d) Acetamide

61. Allyl cyanide contain - and -bonds [MP PET 2004]

(a) 9 , 3  (b) 9 , 9 

(c) 3 , 4  (d) 5 , 7 

62. Strongest acid is [MP PMT 2004]

(a) HCCH

(b)

2 6

CH

(c)

6 6

CH (d) CH OH

3

63.CC bond is found in [BHU 1982; MP PMT 1994]

(a) Ethene (b) Butene

(c) Ethyne (d) Glycerine

64. Number of  bonds in [CPMT 1994]

(a) 6 (b) 15

(c) 10 (d) 12

65. Number of bonds in benzene [DPMT 2005]

(a) 6  and 3  (b) 12  and 3 

(c) 3  and 12  (d) 6  and 6 

66. Which is most acidic of the following [J & K 2005]

(a) Methane (b) Acetylene

(c) 1 - butene (d) Neo-pentane

67. The enolic form of acetone contains [Pb. PMT 2002]

(a) 8 bonds, 2 -bonds and 1 lone pairs

(b) 9 -bonds, 1 -bond and 2 lone pairs

(c) 9 -bonds, 2 -bonds and 1 lone pairs

(d) 10

  • bonds, 1
  • bonds and 1 lone pairs

Dipole moment, resonance and reaction

intermediates

1. Which has zero dipole moment [NCERT 1990; BHU 2001]

CH 3

(a) cis - 2 - butene (b) trans - 2 - butene

(c) 1 - butene (d) 2 - methyl- 1 - propene

2. Dipole moment is shown by [DCE 1999]

(a) 1, 4-dichloro benzene

(b) Cis-1, 2-dichloro ethane

(c) Trans-1, 2-dichloro, 2-pentene

(d) Trans-1, 2-dichloro ether

3. Which compound shows dipole moment [RPMT 2002]

(a) 1,4-di-chloro benzene

(b) 1, 2-di-chloro benzene

(c) Trans-1, 2-di-chloro ethene

(d) Trans- 2 - butene

4. Which of the following is a polar compound

[MH CET 2003]

(a)

2 6

CH

(b)

4

CCl

(c) HCl (d)

4

CH

5. The dipole moment is the highest for [AIIMS 2004]

(a) Trans - 2 - butene (b) 1, 3-Dimethylbenzene

(c) Acetophenone (d) Ethanol

6. Resonance structure of molecule does not have

[IIT-JEE 1984]

(a) Identical arrangement of atoms

(b) Nearly the same energy content

(c) The same number of paired electrons

(d) Identical bonding

7. All bonds in benzene are equal due to

[Roorkee 1990; KCET 1998]

(a) Tautomerism (b) Inductive effect

(c) Resonance (d) Isomerism

8. Aromatic properties of benzene are proved by

[MP PMT 1994]

(a) Aromatic sextet theory (b) Resonance theory

(c) Molecular orbital theory (d) All of these

9. Which of the following will show aromatic

behaviour

[KCET 1996]

(a) (b)

(c) (d)

10. Which one of the following orders is correct

regarding the inductive effect of the substituents [CBSE PMT 1998]

(a) NR  OR  F

2

(b) NR  OR  F

2

(c)  NR  OR  F

2

(d) NR  OR  F

2

11. Benzene is unreactive because [KCET 1998]

(a) It has double bonds

(b) It has carbon-carbon single bond

(c) Carbon are

2

sp hybridised

(d)  electrons are delocalised

12. Carboxylic acids are easily ionised. The main

reason of this statement [UPSEAT 1999]

(a) Absence of -hydrogen

(b) Resonance stabilisation of carboxylate ion

(c) Reactivity of -hydrogen

(d) Hydrogen bond

13. ' CC 'bond length in benzene lies between single

and double bond. The reason is [RPET 1999]

(a) Resonance (b) Isomerism

(c) Metamerism (d) Inductive effect

14. Credit for the ring structure of benzene goes to

[RPET 1999]

(a) Wholer (b) Faraday

(c) Kekule (d) Baeyer

15. Polarisation of electrons in acroline may be

written as

[DCE 2000]

(a) CHCHCHO

 

2

(b)

 

  

 

CH CH CH O

2

(c) CHCHCHO

 

2

(d)

 

  

 

CH CH CH O

2

16. In the mixture of conc.

2 4

HSO and

3

HNO the

nitrating species is [MP PMT 2000]

(a)

2 4

NO (b)

2

NO

(c)

2

NO (d)

2

NO

17. Which of the following are not aromatic [DCE 2001]

(a) Benzene

(b) Cyclo-octatetrarenyl dianion

(c) Tropyllium cation

(d) Cyclopentadienyl cation

18. Arrangement of

3 3 23 3 2 3

( CH )  C ( CH )  CH  CH  CH  CH

when

attached to benzyl or an unsaturated group in

increasing order of inductive effect is [AIE

(a)      

3 3 32 3 2

( CH ) C ( CH ) CH CH CH

(b) CHCH  CHCH  CHC

3 2 32 33

(c)      

3 2 33 3 2

( CH ) CH ( CH ) C CH CH

(d) CHC  CHCH  CHCH

2 3 3 2 32

19. Which of the following is observed in ethylene

molecule

[MH CET 2002]

(a) Electromeric effect (b) Inductive effect

(c) Homolytic fission (d) None of these

20. Cyclopentadienyl anion is [Orissa JEE 2003]

(a) Aromatic (b) Non-aromatic

(c) Non-planar (d) Aliphatic

21. Orbital interaction between the sigma bonds of a

substitutent group and a neighbouring pi orbital

is known as

O

[BHU 1985]

(a) Carbocation (b) Carbanion

(c) Free radical (d) None of these

36. Which of the following carbanion is most stable

[NCERT 1983]

(a) Methyl (b) Primary

(c) Secondary (d) Tertiary

37. Among the given cations, the most stable

carbonium ion is

[IIT-JEE 1981]

(a) sec - butyl (b) ter - butyl

(c) n - butyl (d) None of these

38. In the compound given below

The correct order of the acidity of the positions

( X ), ( Y ) and ( Z ) is [IIT-JEE Screening 2004]

(a) ( Z ) > ( X ) > ( Y ) (b) ( X ) > ( Y ) > ( Z )

(c) ( X ) > ( Z ) > ( Y ) (d) ( Y ) > ( X ) > ( Z )

39. C-C bond length in benzene is

[MP PMT 1987; MP PMT 2001; AIIMS 2001]

(a) 1.39 Å

(b) 1.

Å

(c) 1.34 Å

(d) Different in different bonds

40. Heterolysis of carbon-chlorine bond produces

[MNR 1986; MP PET/PMT 1998]

(a) Two free radicals

(b) Two carbonium ions

(c) Two carbanions

(d) One cation and one anion

41. In , 3 2

CHCHOH the bond that undergoes

heterolytic cleavage most readily is [IIT-JEE 1988]

(a) CC (b) CO

(c) CH (d) OH

42. Which of the following intermediate have the

complete octet around the carbon atom [Orissa JEE 2003]

(a) Carbonium ion (b) Carbanion ion

(c) Free radical (d) Carbene

43. A solution of D (+) - 2 - chloro- 2 - phenylethane in

toluene racemises slowly in the presence of small

amount of ,

5

SbCl due to the formation of [IIT-JEE 1999]

(a) Carbanion (b) Carbene

(c) Free radical (d) Carbocation

44. The reagent in Friedel Craft's reaction is [DPMT 2005]

(a) Pyridine (b) RCOCl

(c) RCOOH (d) HCl

45. Which gives monosubstituted product [DPMT 2005]

(a) o - dinitrobenzene (b)

m

  • dinitrobenzene

(c) p

  • dinitrobenzene (d) Nitrobenzene 46. An aromatic compounds among other things

should have a -electron cloud containing

electrons where n can't be

[J & K 2005]

(a) 1/2 (b) 3

(c) 2 (d) 1

47. Which of the following is an electrophile [J & K 2005]

(a) H O

2

(b)

3

SO

(c)

3

NH (d) ROR

48. The presence of the chlorine atom on benzene

ring makes the second substituent enter at a

position [J & K 2005]

(a) ortho (b) meta

(c) para (d) ortholpara

49. Which is the most stable carbocation [J & K 2005]

(a) iso-propyl (b) Triphenylmethyl

cation

(c) Ethyl cation (d) -propyl cation

Organic reactions and their mechanism

1. To which of the following four types does this

reaction belong

 

BRABRA [Manipal MEE 1995]

(a) Unimolecular electrophilic substitution

(b) Bimolecular electrophilic substitution

(c) Unimolecular nucleophilic substitution

(d) Bimolecular nucleophilic substitution

2. An alkyl halide may be converted into an alcohol

by

[Pb. PMT 2000]

(a) Elimination (b) Addition

(c) Substitution (d) Dehydrohalogenation

CH CHCl

3 2

The above reaction proceeds through [AMU 2000]

(a) Nucleophilic substitution

(b) Electrophilic substitution

(c) Free radical substitution

(d) More than one of the above processes

4. Geometry of reaction intermediate in

1

SN

reaction is

[MH CET 2001]

(a) Tetrahedral (b) Planar

(c) Triangular bipyramidal (d) None of these

OH KBr

CH

CH

Br KOHAq HC C

CH

CH

H CC      

3

3

|

|

3

3

3

|

|

3

( .)

above reaction is [RPMT 2003]

COOH

( X )

NH

3

( Z )

H 3

N

( Y )

(a)

1

SN (b)

2

SN

(c)

1

E (d) Both (a) and (b)

6. In electrophilic substitution reaction nitrobenzene is

[Kerala (Med.) 2003]

(a) Meta-directing

(b) Ortho-directing

(c) Para-directing

(d) Not reactive and does not undergo any

substitution

(e) Non-selective

7. The most common type of reaction in aromatic

compounds is [Orissa JEE 2003]

(a) Elimination reaction

(b) Addition reaction

(c) Electrophilic substitution reaction

(d) Rearrangement reaction

8. The function of 3

AlCl in Friedel-Craft’s reaction is

[KCET 2003]

(a) To absorb HCl (b) To absorb water

(c) To produce nucleophile (d)To produce electrophile

9. Which of the following can’t be used in Friedal

Craft’s reactions [AFMC 2004]

(a)

3

FeCl (b)

2

FeBr

(c)

3

AlCl

(d) NaCl

10. The nitration of a compound is due to the [Pb. PMT 2004]

(a)

2

NO (b)

3

NO

(c) NO (d)

2

NO

11. Dehydrohalogenation of an alkyl halide is a/an

[MH CET 2004]

(a) Nucleophilic substitution reaction

(b) Elimination reaction

(c) Both nucleophilic substitution and elimination

reaction

(d) Rearrangement

12. Addition of HCl to vinyl chloride gives 1, 1 -

dichloroethane because of [MP PET 2004]

(a) Mesomeric effect of Cl

(b) Inductive effect of Cl

(c) Restricted rotation around double bond

(d) None of these

13. Formation of ethylene from acetylene is an

example of

(a) Elimination reaction (b) Substitution reaction

(c) Addition reaction (d) Condensation

reaction

14. Conversion of 4

CH to CHCl

3

is an example of

which of the following reaction [Pb. CET 2001]

(a) Electrophilic substitution

(b) Free radical addition

(c) Nucleophilic substitution

(d) Free radical substituion

15. Following reaction,

CH CBrHOCH COHHBr

3 3 2 33

( ) ( ) is an example

of

[DCE 2002]

(a) Elimination reaction (b) Free radical

substitution

(c) Nucleophilic substitution(d)Electrophilic substitution

16. Which is an electrophile [DCE 2002]

(a)

3

BCl

(b) CHOH

3

(c)

3

NH (d)

4

AlCl

17. The electrophile in the nitration of benzene is

[Orissa JEE 2004]

(a)

2

NO (b)

2

NO

(c)

NO (d)

2

NO

18. The following compound will undergo

electrophilic substitution more readily than

benzene [UPSEAT 2004]

(a) Nitrobenzene (b) Benzoic acid

(c) Benzaldehyde (d) Phenol

19. Which represents nucleophilic aromatic

substitution reaction

[Orissa JEE 2004]

(a) Reaction of benzene with

2

Cl in sunlight

(b) Benzyl bromide hydrolysis

(c) Reaction of NaOH with dinitrofluorobenzene

(d) Sulphonation of benzene

20. Which is an electrophile [DCE 2000]

(a)

3

AlCl (b)

CN

(c)

3

NH

(d) CH OH

3

21. Strongest nucleophile is [BHU 2003]

(a)

2

RNH (b) ROH

(c)

C H O

6 5

(d)

CH O

3

22. The major product obtained when Br / Fe

2

is

treated with

is

[IIT-JEE Screening 2004]

(a) (b)

(c) (d)

23. Which one of the following is least reactive in a

nucleophilic substitution reaction [CBSE PMT 2004]

(a) CH CHCl

3 2

(b) CH CHCH Cl

2 2

HN

H

3

C

O

CH 3

HN

H 3 C

O

CH 3

Br

HN

H 3 C

O

CH 3

Br

HN

H

3

C

O

CH 3

Br

HN

H

3

C

O

CH 3

Br

[CBSE PMT 1988]

(a)

3

3

CH

CH  CH  COOH

(b)

2 2 2 3

CH  CHCH CHCH

(c)

2

3 3

NH

CH  CH  CH

(d)

2

3 2 3

NH

CH  CH  CH  CH

8. Which of the following compounds may not exist

as enantiomers [CPMT 1987]

(a) CH CHOHCOH

3 2

(b) CH CHCHCH CH OH

3 2 3 2

(c)

6 5 2 3

CHCHCH

(d)

6 5 3

CHCHClCH

9. Number of isomers of molecular formula

2 2 2

CHBr

are

[CPMT 1987]

(a) 1 (b) 2

(c) 3 (d) 0

10. Lactic acid shows which type of isomerism

[CPMT 1987; MP PMT 1987; BHU 2003]

(a) Geometrical isomerism (b) Tautomerism

(c) Optical isomerism (d) Metamerism

11. Which one of the following is an optically active

compound

[CBSE PMT 1988; DPMT 1983]

(a) n - propanol (b) 2 - chlorobutane

(c) n - butanol (d) 4 - hydroxyheptane

12. Compounds with same molecular formula but

different structural formulae are called [BHU 1979; AFMC 1989]

(a) Isomers (b) Isotopes

(c) Isobars (d) Isoelectronic

13. Which one of the following compounds shows

optical isomerism [MP PET 1990]

(a)

3 2 3

CH CHClCHCH

(b)

3 2 2 3

CHCHCHClCHCH

(c)

2 2 2 3

ClCHCHCHCH

(d)

2 2 3

ClCHCHCH

14. Which one of the following objects is ‘achiral’

(a) Letter P (b) Letter F

(c) Ball (d) A pair of hand

15. Total number of isomers of a disubstituted

benzene compound is

(a) 1 (b) 2

(c) 3 (d) 4

16. Separating of d and l enantiomorphs from a

racemic mixture is called [CBSE PMT 1988; DPMT 1983;

KCET 2002]

(a) Resolution (b) Dehydration

(c) Rotation (d) Dehydrohalogenation

17. Number of optical isomers of lactic acid are

(a) 1 (b) 2

(c) 3 (d) 4

18. Which one of the following contains asymmetric

carbon atom [IIT-JEE 1989; Roorkee 2000]

(a) H

H

Br

C

H

Cl

H C

   (b) Cl

H

Cl

C

H

H

H C

(c) H

H

H

C

H

H

H C

   (d)

3

CH

OH

H

C

Br

H

H  C  

19. n - butane and isobutane are examples of

(a) Chain isomers (b) Geometrical isomers

(c) Position isomers (d) Tautomers

20. Which of the following has chiral structure

(a) CHCOOH

CH

CH CH

2

3

3

(b)

3 3

CH  CH  CH  CH

(c) CHOH

CH

CH CH

2

3

3

(d)

3 2 3

CH  CHOH  CHCH

21. Which of the following pairs is an example of

position isomerism

(a)

3 2 2 3

CHCHCHCH and

3

3

3

|

CH

CH

CHCH

(b)

3 2 2

CHCHCHCH and

3 3

CH  CH  CH  CH

(c) CH CHOH

3 2

 and

3 3

CH  O  CH

(d)

3

3

3 3

|

|

CH

CH

CHCCH and

3 2 2 2 3

CH  CH  CH  CH  CH

22. Geometrical isomerism is shown by

[IIT-JEE 1983; CPMT 1990, 94; CBSE PMT 1992;

MP PET 1997; AMU (Engg.) 1999]

(a) 2 - butene (b) 2 - butyne

(c) 2 - butanol (d) Butanal

23. An organic compound exhibits optical isomerism

when

[CPMT 1971, 78, 81; MP PET 1999]

(a) Four groups linked to carbon atom are

different

(b) Three groups linked to carbon atom are

different

(c) Two groups linked to carbon atom are

different

(d) All the groups linked to carbon atom are same

24. Which one of the following exhibits geometrical

isomerism

[NCERT 1979; DPMT 1984; CBSE PMT 1990]

(a)

3 3

CH

H

C C

HC

H

 (b)

H

H

C C

H

C H

2

(c)

H

H

C C

CH

CH

3

3

(d)

H

H

C

H

C

CH

H

H  C  

|

3

|

|

25. Maximum number of isomers of alkene 4 8

CH are

[IIT-JEE 1982; MP PMT 1985; MADT Bihar 1995;

Kerala (Engg.) 2002]

(a) 2 (b) 3

(c) 4 (d) 6

26. Rotation of plane polarised light is measured by

[CPMT 1985; DCE 2001]

(a) Manometer (b) Polarimeter

(c) Viscometer (d) Refractometer

27. An alkane forms isomers if the number of least

carbon atom is [CPMT 1976; BHU 1985, 89]

(a) 1 (b) 2

(c) 3 (d) 4

28. Which is not found in alkenes [AIIMS 1982; RPMT 1999]

(a) Chain isomerism (b) Geometrical

isomerism

(c) Metamerism (d) Position isomerism

29. How many isomers of C H OH 5 11

will be primary

alcohols

[CBSE PMT 1992]

(a) 2 (b) 3

(c) 4 (d) 5

30. The compound C H O 4 10

can show

[IIT-JEE 1981; MP PET 2000]

(a) Metamerism (b) Functional

isomerism

(c) Positional isomerism (d) All types

31. The number of possible alcoholic isomers for

C H O

4 10

are

[DPMT 1984; MNR 1986]

(a) 4 (b) 2

(c) 3 (d) 5

32. How many isomers are possible for C HO 4 8

[MNR 1992; UPSEAT 2001, 02]

(a) 3 (b) 4

(c) 5 (d) 6

33. Which of the following can exhibit cis-trans

isomerism

[CBSE PMT 1989]

(a) HCCH (b) ClCH = CHCl

(c) CH. CHCl. COOH

3

(d) ClCH CHCl

2 2

34. The number of geometrical isomers in case of a

compound with the structure

3 2 5

CHCHCHCHCHCH is

[NCERT 1980]

(a) 4 (b) 3

(c) 2 (d) 5

35. The property by virtue of which a compound can

turn the plane polarised light is known as [BHU 1979]

(a) Photolysis (b) Phosphorescence

(c) Optical activity (d) Polarization

36. Meso-tartaric acid is optically inactive due to the

presence of

[AIIMS 1982; MP PMT 1987]

(a) Molecular symmetry

(b) Molecular asymmetry

(c) External compensation

(d) Two asymmetric C-atoms

37. Which of the following compounds exhibits

optical isomerism [BHU 1983; AFMC 1990; CPMT 1993;

MP PMT 1999, 2000]

(a) CH CHCOOH

3 2

(b) CH CHOHCOOH

3

(c) CH CHCHOH

3 2 2

(d)

3 3

CHCHOHCH

38. The maximum number of stereoisomers possible

for 2-hydroxy- 2 - methyl butanoic acid is [Roorkee 1992]

(a) 1 (b) 2

(c) 3 (d) 4

39. Which one of the following pairs represents the

stereoisomerism [AIIMS 1992]

(a) Geometrical isomerism, position isomerism

(b) Geometrical isomerism, conformational

isomerism

(c) Optical isomerism, geometrical isomerism

(d) Optical isomerism, metamerism

40. Diethyl ether is not associated with which one of

these isomers [AFMC 1993]

(a) Butanoic acid (b) Methyl propionate

(c) Steroisomerism (d) None of these

41. Diethyl ether and methyl n- propyl ether are

[MP PET 1994; AFMC 1999; MP PMT 2002]

(a) Position isomers (b) Functional isomers

(c) Metamers (d) Chain isomers

42. n- propyl alcohol and isopropyl alcohol are

examples of

[MP PMT 1994]

(a) Position isomerism (b) Chain isomerism

(c) Tautomerism (d) Geometrical

isomerism

43. It is possible to distinguish between optical

isomers by

63. cis and trans 2 - butene are [BHU 1998; DPMT 2002]

(a) Conformational isomers (b) Optical isomers

(c) Position isomers (d) Geometrical isomers

64. Which one of the following is the chiral molecule

[BHU 1998; 2005]

(a) CH Cl

3

(b)

2 2

CHCl

(c)

3

CHBr (d) CHClBrI

65. Cyanide and isocyanide are isomers of type [AFMC 1997]

(a) Positional (b) Functional

(c) Tautomer (d) Structural

66. Glucose and fructose are [AMU (Engg.) 1999]

(a) Optical isomers (b) Functional isomers

(c) Position isomers (d) Chain isomers

67. Which of the following compounds which is an

optically active compound [UPSEAT 1999]

(a) 1 - butanol (b) 2 - butanol

(c) 3 - butanol (d) 4 - heptanol

68. d - tartaric acid and l - tartaric acid are [MH CET 1999]

(a) Enantiomers (b) Tautomers

(c) Diastereoisomers (d) Structural isomers

69. Minimum resistance in bond rotation will be

observed in the compound [RPMT 1999]

(a) Hexachloroethane (b) Ethylene

(c) Acetylene (d) Ethane

70. Which pair show cis-trans isomerism [RPET 1999]

(a) Maleic-fumaric acid (b) Lactic-tartaric acid

(c) Malonic-succinic acid (d)Crotonic-acrylic acid

71. 1, 2-Dichloroethene shows [RPET 1999]

(a) Geometrical isomerism (b) Optical isomerism

(c) Ring-chain isomerism (d) Resonance

72. Which compound is optically active [DCE 1999]

(a) 4 - chloro, 1 hydroxy butane

(b)

o

3

  • butyl alcohol

(c) Secondary butyl amine

(d) n - butyl alcohol

73. Choose the pair of chain isomer [RPMT 2000]

(a)

3 2

CHCHBr and CH BrCHBr

2 2

(b) 1 - propanol and 2-propanol

(c) Neo-pentane and isopentane

(d) Diethyl ether and methyl- n - propyl ether

74. Optical isomerism arises due to the presence of

[RPMT 2000]

(a) An asymmetric carbon atom

(b) Centre of symmetry

(c) Axis of symmetry

(d) Plane of symmetry

75. Least hindered rotation about carbon-carbon bond

is observed in [RPMT 2000]

(a) Ethane (b) Ethylene

(c) Ethyne (d) Hexachloroethane

76. Which pair represents chain isomer [RPMT 2000]

(a)

3 2

CHCHCl and ClCH CHCl

2 2

(b) n - propyl alcohol and isopropyl alcohol

(c) 2 - methy l - 1 propanol and 2-Methyl-2 propanol

(d) 2 - methyl butane and neopentane

77. Which of the following compounds will exhibit

geometrical isomerism [IIT-JEE Screening 2000]

(a) 1 - phenyl- 2 - butene (b) 3 - phenyl- 1 - butene

(c) 2 - phenyl- 1 - butene (d) 1, 1 - Diphenyl- 1 -

propene

78. On bromination, propionic acid yields two

isomeric 2-bromopropionic acids. This pair is an

important example of [BHU 2000]

(a) Chain isomers (b) Optical isomers

(c) Cis-trans isomers (d) Position isomers

79. Geometrical isomerism is not possible in [CPMT 2000]

(a) Propene (b) 3 - hexane

(c) Butenedioic acid (d) Cyclic compound

80. Only two isomeric monochloro derivatives are

possible for

[Pb. PMT 2000]

(a) 2 - methyl propane (b) n - pentane

(c) Benzene (d) 2, 4 - dimethyl

pentane

81. Lactic acid in which a methyl group, a hydroxyl

group, a carboxylic acid group and a hydrogen

atom are attached to a central carbon atom,

shown optical isomerism due to the molecular

geometry at the [Pb. PMT 2000]

(a) Central carbon atom

(b) Carbon atom of the methyl group

(c) Carbon atom of the carboxylic acid group

(d) Oxygen of the hydroxyl groups

82. The number of possible alkynes with molecular

formula

5 8

CH is [MP PMT 2000]

(a) 2 (b) 3

(c) 4 (d) 5

83. Which of the following will not lose asymmetry

on reduction with

4

LiAlH [Roorkee 2000]

(a)

2

2 2 3

CH CH

CHCH

CHO

HOHC

(b)

2 3

3

2

CH CH

CHO

CH

H C  HCO

(c)

C CH

COOH

CH

HOHC

3

2

(d)

2 2

3

CH NH

C N

CHO

H C 

84. Reason for geometrical isomerism by 2-butene is

[CBSE PMT 2000]

(a) Chiral carbon

(b) Free rotation about single bond

(c) Free rotation about double bond

(d) Restricted rotation about double bond

85. Stereoisomers which are not the mirror images of

one another are called [RPMT 2000]

(a) Enantiomers (b) Mesomers

(c) Tautomers (d) Diasteroisomers

86. The isomerism shown by n - butyl alcohol and

isobutyl alcohol is [RPMT 2000]

(a) Metamerism (b) Chain

(c) Position (d) Stereo

87. Which is optically active [MH CET 2001]

(a)

2 2

CHCl

(b)

3

CHCl

(c) Meso form of tartaric acid

(d) Glyceraldehyde

88. Which of the following will show geometrical

isomerism

[CPMT 2001; BHU 2005]

(a)

3 3

CH CH  CHCH

(b)

3 2 32

( CH ) C  C ( CH )

(c)

3 2 32

( CH ) C  C ( CH )

(d)

3 32

CH  CH  C ( CH )

89. What is the maximum number of open chain

structures possible for

4 8

CH [MP PET 2001]

(a) 2 (b) 3

(c) 4 (d) 1

90. Glucose has optical isomers [DCE 2001]

(a) 8 (b) 12

(c) 16 (d) Cannot be predicted

91. An organic compound

3

7

2

6

2

5

2

4

2

3

2

2

3

1

CHCHCHCHCHCHCH

To make it chiral compound the attack should be

on which carbon atom [DCE 2001]

(a) 1 (b) 3

(c) 4 (d) 7

92. Which of the following statements is not true

about enantiomers [DCE 2001]

(a) They have same physical properties

(b) They have different biological properties

(c) They have same chemical properties towards

chiral compounds

(d) None of these

93. Meso-tartaric acid is [BHU 2001]

(a) Optically inactive

(b) Optically active because of molecular

symmetry

(c) Optically inactive due to external

compensation

(d) Optically active because of asymmetric carbon

atom

94. The number of possible isomers of the compound

with molecular formula C HO

7 8

is [BHU 2001]

(a) 3 (b) 5

(c) 7 (d) 9

95. The number of isomers for the compound with

molecular formula CBrClFI

2

is [IIT-JEE (Screening) 2001]

(a) 3 (b) 4

(c) 5 (d) 6

96. Hydrogenation of the adjoining compound in the

presence of poisoned palladium catalyst gives

[IIT-JEE (Screening) 2001]

Me H

MeH

(a) An optically active compound

(b) An optically inactive compound

(c) A racemic mixture

(d) A diastereomeric mixture

97. The number of possible structural isomers for a

compound with the molecular formula

7 16

CH is [DCE 2001]

(a) 8 (b) 9

(c) 10 (d) 12

98. Which of the following molecule contains

asymmetric carbon atom [JIPMER 2002]

(a) CHCHClCOOH

3

(b) CH CHCOOH

3 2

(c) ClCH CHCOOH

2 2

(d) ClCHCOOH

2

99. A similarity between optical and geometrical

isomerism is that [AIEEE 2002]

(a) Each forms equal number of isomers for a

given compound

(b) If in a compound one is present then so is the

other

(c) Both are included in stereoisomerism

(d) They have no similarity

100. If the light waves pass through a nicol prism then

all the oscillations occur only in one plane, such

beam of light is called as [Kerala (Med.) 2002]

(a) Non-polarised light (b) Plane polarised light

(c) Polarised light (d) Optical light

101. Racemic mixture is formed by mixing two [AIEEE 2002]

(a) Isomeric compounds (b) Chiral compounds

(c) Meso compounds (d) Optical isomers

102. Which of the following does not show geometrical

isomerism [AIEEE 2002]

(a) 1, 2 dichloro- 1 - pentene

(b) 1, 3-dichloro- 2 - pentene

(c) 1, 1-dichloro- 1 - pentene

(d) 1, 4-dichloro- 2 - pentene

Me

H

120. An enantiomerically pure acid is treated with

racemic mixture of an alcohol having one chiral

carbon. The ester formed will be [IIT-JEE (Screening) 2003]

(a) Optically active mixture (b) Pure enantiomer

(c) Meso compound (d) Racemic mixture

121. Which one of the following will not show

geometrical isomerism [MP PMT 2003]

(a)

H Br

C C

HC Cl

3

(b)

HC Br

C C

HC Cl

3

3

(c)

D Br

C C

H Cl

 (d)

Br Br

C C

Cl Cl

122. Isomerism shown by

3 23 3

CH ( CH )  O  CH

3 2 2 2 3

CH  CH  O  CH  CH  CH

2 3

3

3

|

O CH CH

CH

CHCH    is [RPMT 2003]

(a) Position isomerism (b) Chain isomerism

(c) Metamerism (d) Optical isomerism

123. A compound whose molecules are superimposable

on their mirror images even through they contain

an asymmetric carbon atom is called [Kerala (Med.) 2003]

(a) A meso compound (b) An erythro isomer

(c) A threo isomer (d) a glycol

124. Of the following, the compound possessing optical

isomerism [Kerala (Med.) 2003]

(a) CH CHOH

3 2

(b) CHCHClBr

3

(c) CCl BrF

2

(d)

2 2

CClF

125. Which of the following statement is wrong [EAMCET 2003]

(a) Diethyl ketone and methyl propyl ketone are

position isomers

(b) 2 - chloro pentane and 1 - chloro pentane are

position isomers

(c) n - butane and 2 - methyl propane are chain

isomers

(d) Acetone and propinaldehyde are functional

isomers

126. Dimethyl ether and ethyl alcohol are

[MH CET 2004; Pb. CET 2002]

(a) Metamers (b) Homologues

(c) Functional isomers (d) Position isomers

127. The correct statement about the compounds A

and B is

[DCE 2002; UPSEAT 2004; IIT-JEE 1997; DPMT 2005]

COOH

H OH

H OH

COOCH

3

3

COOCH

H OH

H OH

COOH

(A) (B)

(a) A and B are identical

(b) A and B are diastereomers

(c) A and B are enantiomers

(d) None of these

128. Ethyl acetoacetate shows, which type of

isomerism

[Pb. CET 2003]

(a) Chain (b) Optical

(c) Metamerism (d) Tautomerism

129. Which of the following will have a mesoisomer

also

[AIEEE 2004]

(a) 2, 3-Dichloropentane

(b) 2, 3-Dichlorobutane

(c) 2 - Chlorobutane

(d) 2 - Hydroxypropanoic acid

130. For which of the following parameters the

structural isomers C HOH

2 5

and

3 3

CHOCH would

be expected to have the same values? (Assume

ideal behaviour) [AIEEE 2004]

(a) Boiling points

(b) Vapour pressure at the same temperature

(c) Heat of vaporization

(d) Gaseous densities at the same temperature

and pressure

131. The geometrical isomerism is shown by [AIIMS 2004]

(a) (b)

(c) (d)

132. Which of the following compounds will exhibit

cis-trans isomerism [Kerala PMT 2004]

(a) 2 - butene (b) 2 - butyne

(c) 2 - butanol (d) Butanone

(e) Butanol

133. Which of the following compounds exhibit

stereoisomerism

[MP PMT 2004]

(a) 2 - methyl-butane I (b) 3 - methyl-butanoic

acid

(c) 3 - methyl-butyne I (d) 2 - methyl butanoic

acid

134. The chirality of the compound [CBSE PMT 2005]

HC Cl

H

Br

C

3

|

(a) R (b) S

(c) Z (d) E

135. Which of the following is most likely to show

optical isomerism [UPSEAT 2004]

(a) C CH

H

Cl

HC  C  C  

|

|

(b)

3

|

|

CH

H

Cl

HC  C  C 

CH

2

CH

2

CH Cl

CH Cl

(c) H

H

Cl

HC  C  C 

|

|

(d)

2

|

CH

Cl

HC  C  C 

136. Nitroethane can exhibit one of the following kind

of isomerism [DCE 2004]

(a) Metamerism (b) Optical activity

(c) Tautomerism (d) Position isomerism

137. CH CH ( OH ). COOH

3

shows [BVP 2004]

(a) Geometrical isomerism (b) Optical isomerism

(c) Both (d) None

138. Which will have enantiomer [BVP 2004]

(a)

3

|

3 2

CH

Cl

CH CH CH  (b) CH CHCHCHCl

2 2 2 2

(c)

3 2 2 2

CHCHCHCHCl

(d) None

139. The total number of acylic isomers including the

stereoisomers with the molecular formula C HCl

4 7

[Pb. CET 2004]

(a) 11 (b) 12

(c) 9 (d) 10

140. The number of possible enantiomeric pairs that

can be produced during mono-chlorination of 2-

methylbutane is

[Pb. CET 2004]

(a) 3 (b) 4

(c) 1 (d) 2

141. Which one of the following pairs represents

stereoisomerism

[CBSE PMT 2005]

(a) Chain isomerism and rotational isomerism

(b) Structural isomerism and geometric

isomerism

(c) Linkage isomerism and geometric isomerism

(d) Optical isomerism and geometric isomerism

142. When isomers have the same structural formula

but differ in relative arrangement of atoms or

groups are called

[CPMT 2000; KCET (Med.) 2000]

(a) Mesomers (b) Stereoisomers

(c) Optical isomers (d) Geometrical

mesomers

3 2 2

CH CH CHCH and

3 3

CHCHCHCH show

(a) Chain isomerism (b) Position isomerism

(c) Functional isomerism (d) Metamerism

144. The number of possible isomers of butene are

[Kerala (Engg.) 2002]

(a) 3 (b) 2

(c) 4 (d) 5

(e) 6

145. Which of the following show geometrical

isomerism

[BCECE 2005]

(a) C HBr

2 5

(b)

2 2

( CH )( COOH )

(c)

2 2

( CH )( COOH ) (d)

2 6

CH

146. Among the following the most stable compound is

[AIIMS 2005]

(a) cis  1 , 2  cyclohexanediol

(b) trans  1 , 2  cyclohexanediol

(c) cis  1 , 3  cyclohexanediol

(d) trans  1 , 3  cyclohexanediol

147. Chirality of carbon compound is because of its

[Kerala (Med.) 2002]

(a) Tetrahedral nature of carbon

(b) Monovalent nature of carbon

(c) Divalent nature of carbon

(d) Trivalent nature of carbon

148. Which kind of isomerism is possible for 1-chloro-

2 - nitroethene [J & K 2005]

(a) Functional group isomerism

(b) Position isomerism

(c) E / Z isomerism

(d) Optical isomerism

149. Which will give chiral molecule [DPMT 2005]

(a)   

4

3

LiAlH

CH COCl

(b)

H HO

CHMgBr

C H CHO

2

3

/

2 5

(c)  

Cu

CH CHC H

3 2 2 5

( )

(d)   

2

3

3

3

Cl

CH

CH

C C

CH

H

150. Which of the following will be chiral

[J & K 2005]

(a)

3 2

CHCHCl (b) CHCHBrCl

3

(c)

2

2

CDCl (d) CH ClBr

2

151. Which of the following fischer projection formula

is same as D - Glyceraldehyde [Kerala CET 2005]

(a)

H

OH CHO

CH OH

2

(b)

CHO

H OH

CH OH

2

(c)

H

OH CHOH

CHO

2

(d)

HO

H CHOH

CHO

2

(e)

CHO

OH CHOH

H

2

14. The number of possible isomers for compound

C HClBr

2 3 2

is [MP PMT 1999]

(a) 2 (b) 3

(c) 4 (d) 5

15. The optically active tartaric acid is named as D-

(+)- tartaric acid because it has a positive [IIT-JEE 1999]

(a) Optical rotation and is derived from D - glucose

(b) pH in organic solvent

(c) Optical rotation and is derived from D (+)

glyceraldehyde

(d) Optical rotation only when substituted by

deuterium

16. Among the following compounds (I-III) the

correct order of reaction with electrophilic

reagent is [CBSE PMT 1997]

(a) II > III > I (b) III < I < II

(c) I > II > III (d) I = II > III

17. Carbocation which is most stable [BHU 2003]

(a)

3 2

CHCH (b)

3

CH

(c)

6 5 2

CHCH (d)

3 2 2

CHCHCH

18. Tautomerism is exhibited by

[CBSE PMT 1997; KCET 2002]

(a) CH CNO

3 3

( ) (b) CH NH

3 2

(c)

3 2

RCNO

(d)

2 2

RCH NO

19. Which of the following will have geometrical

isomers

[MP PET 1996; MP PMT 1997; AFMC 1997]

(a) 2 - methylpropene (b) 2 - butene

(c) 1 - butene (d) Propene

20. Examine the following three pairs of possible

isomers

Now state whether the pairs represent identical

compounds or different isomers

(a) All three pairs represent different compounds

(b) ( ia ) and ( ib ) are identical; ( iia ) and ( iib ) are

identical; and ( iiia ) and ( iiib ) are identical

(c) ( ia ) and ( ib ) are isomers; ( iia ) and ( iib ) are

identical; and ( iiia ) and ( iiib ) are isomers

(d) ( ia ) and ( ib ) are identical; ( iia ) and ( iib ) are

identical, and ( iiia ) and ( iiib ) are isomers

21. Tautomerism is exhibited by [IIT-JEE 1998]

(a)

(b)

(c)

(d)

22. The following reaction is described as [CBSE PMT 1997]

3

25 3

3

3 25

( )

| |

( )

CH

CH CH

H

Br HO C

H

C

HC

CH CH

OH

   

(a)

2

SE (b)

1

SN

(c)

2

SN (d)

0

SN

23. Which one of the following represents eclipsed

form of ethane

(a) (b)

(c) (d) None of these

24. Which are the staggered forms of ethane

OCH 3

I I

I

NO 2

II

I

Cl

Cl

(ia

)

CH 3

CH 3

(iia)

COOH

(iiia)

HOOC

Cl

(ib

)

Cl

COOH

COOH

(iii

b)

CH 3

(ii

b)

H 3

C

CH = CH – OH

O O

O

O

O

O

H H

H

H H

H

H H

H

H H

H

H H

H

H H

H

H H

H

C

H H

H

C

2

HH

H

H

H

H

1

H H

H

C

3

H

H

H

C

H

H

H

H H

H

4

(a) 1 and 4 (b) 3 and 4

(c) 2 and 4 (d) 1 and 3

25. Which of the following is the most stable cation

[CBSE PMT 1988; MNR 1988; AIIMS 1985]

(a)

3 2 3

CH CH CHCH

(b)

3

3 3

CH

CH CCH

(c)

3 2 2 2

CH CH CH CH

(d)

3

CH

26. In a reaction of ,

6 5

CHY

the major product (>

60%) is m - isomer, so the group Y is [AIIMS 1997; UPSEAT 2003]

(a)  COOH (b)

2

 NH

(c)  OH (d) Cl

27. Dehydrohalogenation in presence of

OH is

correctly represented by [Orissa JEE 2004]

(a) (b)

(c) (d)

28. Number of structural isomers of C H O 4 10

are

[CPMT 1983, 84, 89, 91; MADT Bihar 1984;

MNR 1984; MP PET 1997; Pb. PMT 1999; MH CET

2003]

(a) 3 (b) 6

(c) 7 (d) 10

29. Among the following the aromatic compound is

[AIIMS 2004]

(a) (b)

(c) (d)

30. Which of the following compounds are not

arranged in order of decreasing reactivity

towards electrophilic substitution [DCE 2003]

(a) Fluoro benzene > chloro benzene > bromo

benzene

(b) Phenol > n - propyl benzene > benzoic acid

(c) Chloro toluene > para-nitro toluene > 2 -

chloro- 4 - nitro toluene

(d) Benzoic acid > phenol > n - propyl benzene

31. Most stable carbonium ion is [Pb. CET 2004]

(a)

5

2

CH

(b)

CH C

3 3

(c)

C H C

6 53

( ) (d)

6 5 2

C HCH

32. Which one of the following species is most stable

[IIT-JEE 1995]

(a)

2 6 4 2

p ON CH CH

(b)

3 6 4 2

p CHO CH CH

(c)

6 4 2

p Cl CH CH

(d)

6 5 2

C H CH

33. Which of the following gives most stable

carbocation by dehydration [RPMT 2002]

(a) CH CHOH

3 2

(b) CH COH

3 3

(c) CHCHOH

3 2

(d)

3 2 2 3

CH  CH  O  CH  CH

34. Which of the following orders regarding relative

stability of free radicals is correct [UPSEAT 2004]

(a) 3° < 2° < 1° (b) 3° > 2° > 1°

(c) 1° < 2° > 3° (d) 3° > 2° < 1°

35. The + I effect of alkyl groups is in the order [DCE 2002]

(a) 2° > 3° > 1° (b) 1° > 2° > 3°

(c) 3° > 2° > 1° (d) None of these

36. Which one has asymmetric C - atom [Roorkee 1995]

(a)

Br

CH CH CH

|

3 2 2

 

(b)

3

3

3

| |

CH

CH

CH

Br

CHCH  

(c)

3 2 3

CH

Br

CH  CH  CH 

(d)

2 2 3

3

3

|

|

CH CH CH

Br

CH

CHC   

37. Which of the following compounds will show

metamerism

[KCET 1996]

(a)

3 2 5

CHCOOCH

(b)

2 5 2 5

C H  S  CH

(c)

3 3

CHOCH (d)

3 2 5

CH  O  CH

38. How many carbon atoms in the molecule

HCOO  CHOH  COOH

2

are asymmetric

[MP PET 2001]

(a) 1 (b) 2

(c) 3 (d) None of these

39. Which of the following act as nucleophiles [Roorkee 1999]

(a)

3 2

CHNH (b)

RO

(c)

3

AlCl (d) CH MgBr

3

40. Which of the following has the highest

nucleophilicity

[IIT-JEE Screening 2000]

(a)

F (b)

OH

(c)

3

CH (d)

2

NH

41. Keto-enol tautomerism is found in

[IIT-JEE 1988; MADT Bihar 1995]

Br

H

OH

Br

H

OH

Br

H

OH

Br

H

OH