ISOMERISM

1. 2. 3. 4. 5. 6. 7. 8. Which is not found in alkenes [AIIMS 1982; RPMT 1999] (a) Chain isomerism (b) Geometrical isomerism (c) Metamerism (d) Position isomerism 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 Name the compound, that is not isomer with diethyl ether [IIT 1981; CPMT 1989; MADT Bihar 1995] (a) n-propylmethyl ether (b) Butane-1-ol (c) 2-methylpropane-2-ol (d) Butanone n-propyl alcohol and isopropyl alcohol are examples of [MP PMT 1994] (a) Position isomerism (b) Chain isomerism (c) Tautomerism (d) Geometrical isomerism 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 Diethyl ether is not associated with which one of the these isomers [AFMC 1993] (a) Butanoic acid (b) Methyl propionate (c) Stereoisomerism (d) None of these How many primary amines are possible for the formula C 4 H11 N [MNR 1995] (a) 1 (b) 2 Number of structural isomers of C 4 H10 O are (c) 3 (d) 4

[CPMT 1983, 84, 89, 91; MADT Bihar 1984; MNR 1984; MP PET 1997; Pb. PMT 1999]

9. 10.

(a) 3 (b) 6 (c) 7 The number of isomers for the compound with molecular formula C2 BrClFI is (a) 3 An isomer of ethanol is (b) 4 (c) 5

(d) 10
[IIT Screening 2001]

(d) 6

[DPMT 1982, 88; CPMT 1973, 75, 78, 84; IIT 1986; BHU 1984, 85; EAMCET 1993; MP PET 1995; RPET 1999; BHU 2000; AFMC 2002]

11.

(a) Methanol (b) Dimethyl ether Which pair represents chain isomer (a) CH 3 CHCl 2 and ClCH 2 CH 2 Cl

(c) Diethyl ether

(d) Etthylene glycol

[RPMT 2000]

(b) n-propyl alcohol and isopropyl alcohol

[RPMT 2000]

12. 13. 14. 15. 16. 17. 18. 19.

(c) 2-methyl-1 propanol and 2-Methyl-2-propanol (d) 2-methyl butane and neopentane The isomerism shown by n-butyl alcohol and isobutyl alcohol is (a) Metamerism (b) Chain (c) Position (d) Stereo Total number of isomers of C6 H14 are (a) 4 CH 3 CH 2 CH (b) 5 CH 2 and CH 3 CH (c) 6 (d) 7

[IIT 1987; DPMT 1983; CPMT 1991; MNR 1990; MP PET 1995; UPSEAT 2001]

CH

CH 3 show
(c) Functional isomerism (c) 3 (c) 5 (c) (d) Metamerism

[MP PAT 1996] [DPMT 1984; MNR 1986]

(a) Chain isomerism (b) Position isomerism The number of possible alcoholic isomers for C 4 H10 O are (a) 4 (b) 2 How many isomers are possible for C4 H 8 O (a) 3 (b) 4 The isomer of diethyl ether is (a) (CH 3 )2 CHOH (b) (CH 3 )3 C OH Isomers have essentially identical (a) Structural formula (b) Chemical properties The total number of isomers formed by C5 H10 is

(d) 5
[MNR 1992; UPSEAT 2001, 02]

(d) 6
[CPMT 1975]

C3 H 7 OH

(d) (C2 H 5 )2 CHOH

[CBSE 1988;MP PMT 1983, 86]

(c) Molecular formula

(d) Physical properties

[Bihar MEE 1996]

20. 21. 22. 23. 24. 25.

(a) 2 (b) 3 (c) 4 (e) None of these n-butane and isobutane are examples of (a) Chain isomers (b) Geometrical isomers (c) Position isomers The number of possible isomers for compound C 2 H 3 Cl 2 Br is (a) 2 (b) 3 Two compounds have the structural formulae CH 3 (c) 4 O CH 2CH 3 and CH 3

(d) 5

(d) Tautomers
[MP PMT 1999]

CH 2

(d) 5 CH 2 OH . The above is an example of (d) Chain isomerism

[MP PMT 2002]

(a) Metamerism (b) Functional isomerism The functional isomer of ethyl alcohol is (a) CH 3 OCH 3 (b) CH 3 COCH 3 Number of isomers of C4 H10 is (a) 2 (b) 3 Which is the example of branch isomerization

(c) Positional isomerism (c)

CH 3 COOH

(d) CH 3 CH 2 CHO
[CBSE 1996; AFMC 1997; RPMT 2002]

(c) 4

(d) Isomerism not exist

[NCERT 1976]

EDUDIGM

Be sincere, not serious

ISOMERISM
C
|

C
| | |

C
|

C
| |

(a) C C C C and C C C

(b) C C C and C C C

C C
(c) 26. 27. 28.

C
| |

C C7 H 9 N has how many isomeric forms that contain a benzene ring

C C

C C C and C C C

(d) C C C C and C C C
|

C
[CPMT 1997, 99] [DCE 2001]

(a) 4 (b) 5 (c) 6 (d) 7 The number of possible structural isomers for a compound with the molecular formula C7 H 16 is (a) 8 (b) 9 The number of possible isomers of butene are (a) 3 (b) 2 (e) 6 Number of isomers of molecular formula C 2 H 2 Br2 are (c) 10 (c) 4 (d) 12 (d) 5

[IIT 1982; MP PMT 1985; MADT Bihar 1995; Kerala (Engg.) 2002]

29. 30.

[CPMT 1987]

(a) 1 (b) 2 (c) 3 Which of the following pairs is an example of position isomerism (a) CH 3

(d) 0

CH 2

CH 2

CH 3 and CH 3

CH
|

CH 3

(b) CH 3

CH 2
CH 3

CH

CH 2 and CH 3

CH

CH

CH 3

CH 3

(c) 31.

CH 3

CH 2 OH and CH 3

O CH 3

(d) CH 3

C CH 3 and CH 3
|

CH 2

CH 2

CH 2

CH 3

CH 3
Examine the following three pairs of possible isomers Cl CH Cl
3

COOH COOH Cl H3 C CH
3

32. 33.

COOH CH HOOC Cl (iiia (ib) (iib) (iiib) (ia) (iia) 3 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 Tautomerism is exhibited by [CBSE 1997; KCET 2002] (a) (CH 3 )3 CNO (b) (CH 3 )2 NH (c) R3 CNO 2 (d) RCH 2 NO 2 Only two isomers of monochloro product is possible of (a) n-butane (b) 2, 4-dimethyl pentane (e) 2-methyl propane Keto-enol tautomerism is found in O O (a)
||

[IIT 1986, 2004; Pb. PMT 2000]

(c) Benzene

(d) 1-methyl propane

[IIT 1988; MADT Bihar 1995]

34.

O
(c)
||

O
(d) H 5 C6
||

O
||

H 5 C6

C H

(b)

||

H 5 C6

C C6 H 5

H 5 C6

C CH 3

C CH 2

C CH 3

35. 36. 37. 38. 39. 40. 41.

The tautomeric form which is less stable is called (a) Anion form (b) Cation form

(c) Labile form

(d) All of the above

[MP PET 1997]

The total number of possible isomeric trimethyl benzene is (a) 2 (b) 3 (c) 4 Glucose and fructose are (a) Optical isomers (b) Functional isomers (c) Position isomers Total number of isomers of a disubstituted benzene compound is (a) 1 (b) 2 (c) 3 The compound C 4 H 10 O can show (a) Metamerism (b) Functional isomerism How many isomers of C5 H11OH will be primary alcohols (a) 2 (b) 3 Which of the following pairs are not isomeric compounds (a) Ethyl ethanoate and methyl propanoate (c) Positional isomerism (c) 4 (b) Butanone and butanal

(d) 6
[AMU (Engg.) 1999]

(d) Chain isomers (d) 4

[IIT 1981; MP PET 2000]

(d) All of the above

[CBSE 1992]

(d) 5

EDUDIGM

Be sincere, not serious

ISOMERISM
(c) Ethoxy propane and propoxy ethane Tautomerism is exhibited by (a) (d) Methoxy methane and ethanol
[IIT 1998]

42.

CH = CH OH

(b) O

(c) OH C6 H 5 C

(d)

O O

43. 44.

N and C6 H 5 N

C exhibit which t ype of isomerism

(c) Dextro isomerism

[CPMT 1997; AFMC 1995, 97]

(a) Position (b) Functional Isomers of propionic acid are (a) (c)

(d) Metamerism
[MP PMT 2002]

HCOOC 2 H 5 and CH 3 COOCH 3 CH 3 COOCH 3 and C3 H 7 OH

(b) HCOOC 2 H 5 and C3 H 7 COOCH 3 (d)

C3 H 7 OH and CH 3 COCH 3
[RPMT 2000]

45.

Choose the pair of chain isomer (a) CH 3 CHBr2 and CH 2 BrCH 2 Br

(b) 1-propanol and 2-propanol ether and methyl-n[CBSE 2001] [MP PET 2001]

46. 47. 48. 49.

(c) Neo-pentane and isopentane (d) Diethyl propyl ether How many structural isomers are possible for a compound with molecular formula C3 H 7 Cl (a) 2 (b) 5 Which of the following compounds shows tautomerism (a) HCHO (b) CH 3 CHO (a) 2 (b) 3 Nitrophenol, C6 H 4 (OH )(NO 2 ) can have (a) No isomer (only a single compound is possible) (c) Three isomers Which of the following compounds will show metamerism (a) CH 3 COOC 2 H 5 (b) C2 H 5 (c) 7 (c) (d) 9

CH 3 COCH 3

(d) HCOOH
[MP PET 2001]

What is the maximum number of open chain structures possible for C 4 H 8 (c) 4 (b) Two isomers (d) Four isomers (d) 1

50. 51. 52.

[KCET 1996]

C2 H 5

(c)

CH 3

O CH 3

(d) CH 3 (d) 9

O C2 H 5
[BHU 2001]

The number of possible isomers of the compound with molecular formula C7 H 8 O is (a) 3 (b) 5 Which will gives colour with FeCl3
OH O
||

(c) 7

(a) 53.
C6 H10 O3 (A)

OH
H3O

(b)

CH 3 C

CHCOC 2 H 5

(c)

OH

(d)

NH2

C4 H 6 O3 (B) C2 H 6 O(C) A, B and C all give iodoform test. A and B also form oximes, A is neutral but B

gives CO 2 with NaHCO 3 . Hence A can be (a) CH 3 COCH 2 COOC 2 H 5 (b) CH 3 CH 2 COCH 2 COOCH 3 54. (c)

CH 3 CH 2 CH 2 COCOOCH

(d) CH 3 CO CH COOCH 3
|

CH 3

CH 3

C CH 2 COOH
||

(I) I2 KOH , (II) H (III)

B , B is
CO CO

O
(a) CH 2 (COOH )2 55.

(b) CH 3 COOH

(c)

CH 2

(d) None of these

C 5 H 12 Cl 2 (A)
(a) CH 3
| |

light

C 5 H 11 Cl (B)
| |

Na/ether

(C) . Only one structure of B is possible. (A), (B) and (C) are
CH 3
| |

CH 3 C CH 3 CH 3 CH 3

CH 3 C CH 2 Cl CH 3 CH 3

CH 3
| |

C CH 2 CH 2 CH 3

C CH 3 CH 3

CH 3
(b) CH 3
|

CH 3
| |

CH 3CH 3
| | | |

C H CH 2 CH 3 CH 3 C CH 2 CH 3 CH 3 CH 2 C Cl

C CH 2 CH 3

CH 3CH 3

(c) Both are correct

EDUDIGM

Be sincere, not serious

ISOMERISM
(d) None of these An organic compound of formula Cn H 2 n O has an acyclic skeleton with no carbon-carbon multiple bonds. If the molecular weight of the compound is 58, which of the following may be the structure of the compound (a) CH 2 CH O CH 3 (b) CH 2 CH CH 3 (c) CH 3 CO CH 3 (d) CH 2
O

56.

CH

CH 2 OH

57.

A(C4 H6 )
is (a) CH 3 C

H 2 / Pt

B(C4 H8 )

O3 / H 2 O / Zn

C
CHCH

HCN

D . D has chiral carbon and can be hydrolysed to lactic acid. Hence A,

(c) (d)

CCH 3

(b) CH 2

CH 2

CH3

58.

C3 H 6 O (A) does not reduce Tollens reagent, does not give iodoform test, but reacts with HI. A can be
(a) CH 3 COCH 3 (b) CH 3 CH 2 CHO
Fe

(c)

CH 2

CHOCH 3

(d) CH 3

CH O

CH 2

59.

60.

C 6 H 4 Cl 2 (dichlorob enzene) Cl 2 C 6 H 3 Cl 3 (trichlorobenzene) . Only one structural isomer of Y is formed. Hence, (X) is (X) (Y) (a) o-isomer (b) p-isomer (c) m-isomer (d) None of these C 6 H 4 Cl 2 (A), dichlorobenzene is chlorinated (without using directive influence rule) to give C 6 H 3 Cl 3 (B). Which are correct
statements (a) ortho-isomer of A will form two types of B (c) para-isomer of A will form one type of B (b) meta-isomer of A will form three types of B (d) All of the above

61.

C4 H 6 O4 (A)

C3 H 6 O2

soda lime

C 2 H 6 ,(A) is
CH 2 COOH | CH 2 COOH
A, ( D is catalyst). A is
O OH
|

(a) CH 3 CH (COOH ) 2

(b)

(c) Both (a) and (b)

(d) None of these

O
62.
||

O
||
D+

CH 3 C CH 2 C OCH 2 CH 3
OH O
||

OD

(a) CH 3 C 63. 64.

CH CO C 2 H 5

(b) CH 3 C CH

||

O
||

C O C2 H 5

(c)

CH 3 C

CH C O C2 H 5

(d) Formation

of

is

not

possible Which is most volatile isomer of nitrophenol (a) o (b) m HCN and HNC are . isomers (a) Functional (b) Tautomers The molecular formula of diphenyl methane, CH2 when one of the hydrogen is replaced by a chlorine atom (a) 8 (b) 7

(c) p (c) Chain

(d) Equal (d) Position

65.

is C13 H12 . How many structural isomers are possible

[CBSE 2004]

(c) 6

(d) 4

66.

67.

Compounds whose molecules are superimposable on their mirror images even though they contain asymmetric carbon atoms or chiral centres are known as (a) Enantiomers (b) Racemers (c) Mesomers (d) Conformers Which one of the following will not show geometrical isomerism [MP PMT 2003] H3C Cl H3C Cl H Cl Cl Cl (a)

C H

C Br

(b)

C H3C

C Br

(c)

C D

C Br

(d)

C Br

C Br
[DPMT 2002]

68. 69.

Butene-2 exhibits (a) Metamerism (a) Position of atoms (c) Spatial arrangement of atoms (b) Geometrical isomerism (c) Optical isomerism (b) Length of carbon (d) (d) None of these Geometrical isomers differ in

[CBSE 2002]

Position of functional group

[MP PET 2002]

H 3C
70.

CH 3 C C H
and

H 3C C H C

H
exhibit which isomerism

CH 3

EDUDIGM

Be sincere, not serious

ISOMERISM
(a) Position isomerism (b) Geometrical isomerism Racemic mixture is formed by mixing two (a) Isomeric compounds 72. 73. 74. Glucose has optical isomers (a) 8 (b) 12 (c) 16 (c) n-butane Which of the following is a chiral compound (a) Hexane (b) Methane Disymmetric object is one which is (a) Superimposable on its mirror image (c) Optically inactive (b) Chiral compounds (c) Optical isomerism (c) Meso compounds (d) Functional isomerism
[AIEEE 2002]

71.

(d) Optical isomers

[DCE 2001]

(d) Cannot be predicted

[AIIMS 2002]

(d) 2, 3, 4-trimethyl hexane

[Kerala (Engg.) 2002]

(b) Non-superimposable on its mirror image (d) Achiral

[CPMT 2000; KCET (Med.) 2000]

75.

When isomers have the same structural formula but differ in relative arrangement of atoms or groups are called (a) Mesomers (b) Stereoisomers (c) Optical isomers (d) Geometrical mesomers 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 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 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 Chirality of carbon compound is because of its (a) Tetrahedral nature of carbon (c) Divalent nature of carbon Which one of the following contains asymmetric carbon atom Cl Br H Cl (a)
| | |

76.

77.

78.

79.

[Kerala (Med.) 2002]

(b) (d)

Monovalent nature of carbon Trivalent nature of carbon

[IIT 1989; Roorkee 2000]

80.

C C H
|

(b)

| |

H H
| | |

H H
(d) H
| | | |

C C Cl
|

(c)

C C H
|

C C CH 3 Br OH

H H
81.

H H

H H

82. 83.

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 ca rbon atom are different (c) Two groups linked to carbon atom are different (d) All the groups linked to carbon atom are same Stereoisomers which are not the mirror images of one another are called [RPMT 2000] (a) Enantiomers (b) Mesomers (c) Tautomers (d) Diastereoisomers Which one is asymmetric C-atom [Roorkee 1995]

CH 3
(a) CH 3 84.
CH 2 CH 2
|

(b) CH 3

CH
|

CH
|

CH 3

(c)

CH 3

CH 2

CH
|

CH 3

(d) CH 3

| |

C CH 2 CH 2 Br

CH 3

Br

Br

CH 3

Br

Which one of the following objects is achiral (a) Letter P (b) Letter F
CH 3 H C CH 3 CH 3 C C

(c) Ball
H COOH

(d) A pair of hand

85.

The following compound can exhibits

[IIT 1995; DCE 2000]

(a) Tautomerism (c) Geometrical isomerism 86. 87. 88. cis and trans 2-butene are (a) Conformational isomers (a) 1-phenyl-2-butene (b)

(b) Optical isomerism (d) Geometrical and optical isomerism

[BHU 1998]

Optical isomers (c) 2-phenyl-1-butene

(c) Position isomers (d) 1, 1-Diphenyl-1-propene

(d)

Which of the following compounds will exhibit geometrical isomerism (b) 3-phenyl-1-butene Reason for geometrical isomerism by 2-butene is

[IIT Screening 2000] [CBSE 2000]

EDUDIGM

Be sincere, not serious

ISOMERISM
(a) Chiral carbon (c) Free rotation about double bond free 89. Which one of the following exhibits geometrical isomerism (b) Free rotation about single bond (d) Restricted rotation about double bond
[NCERT 1979; DPMT 1984; CBSE 1990; AIIMS 2004]

H
(a)

H C C CH 3
CHO
(b)

CH 2 C H C

H
(c)

CH 3 C CH 3
CH 3

H C H
(d) H

CH 3
| |

H
|

C C H H

C H
[Roorkee 2000]

H 3C
90.

Which of the following will not lose asymmetry on reduction with LiAlH4

CH 3
(b)

CHO

(a) 91. 92.

HOH 2 C

CH 2 CH 3 CH CH 2

H 2C

HC

CHO CH 2 CH 3

(c)

HOH 2 C

COOH C CH

(d) H 3 C

C CH 2 NH 2

Which of the following will show geometrical isomerism (a) CH 3 CH

[CPMT 2001]

CHCH 3

(b) (CH 3 )2 C

C(CH 3 )2

(c)

(CH 3 )2 C

C(CH 3 )2

(d) CH 3

CH

C(CH 3 )2

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 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 It is possible to distinguish between optical isomers by [Manipal MEE 1995; AFMC 1995] (a) Infrared spectroscopy (b) Mass spectrometry (c) Melting point determination (d) Polarimetry Geometrical isomerism is not possible in [CPMT 2000] (a) Propene (b) 3-hexene (c) Butenedioic acid Which one of the following compounds shows optical isomerism (a) CH 3 CHCl CH 2 CH 3 (b) CH 3 CH 2 CHCl (c) (d) Cyclic compound
[MP PET 1990]

93. 94. 95. 96.

CH 2

CH 3
[BHU 1979]

ClCH 2

CH 2

CH 2

CH 3

(d) ClCH 2

CH 2

CH 3

97. 98.

The property by vi rtue of which a compound can turn the plane polarised light is known as

(a) Photolysis (b) Phosphorescence (c) Optical activity (d) Polarization The number of optical isomers of an organic compound ha ving n asymmetric carbon atoms will be [MP PET 1994]

(a) 2n 1 (b) n 2 (c) 2n (d) 2n 1 99. Which of the following exhibits optical isomerism [BHU 1980; NCERT 1983; AIIMS 1992; MNR 1993; MP PMT 1990, 94] (a) Butanol-1 (b) Butanol-2 (c) Butene-1 (d) Butene-2 100. Which of the following cannot be given to exemplify chi ral structure [JIPMER 1997] (a) A shoe (b) A screw (c) A screw driver (d) All of the above 101. Which of the following can exhibit cis-trans isomerism [CBSE 1989] (a) HC CH (b) ClCH = CHCl (c) CH 3 .CHCl .COOH (d) ClCH 2 CH 2 Cl 102. The number of enantiomers of the compound CH3CHBrCHBrCOOH is (a) 0 (b) 1 (c) 3 103. Optically active isomers but not mirror images are called (a) Enantiomers (b) Mesomers 104. Chirality is lost when (a) CH 3 CHCOOH is heated
|

[AIIMS 1997]

(d) 4
[MP PET 1999]

(c) Tautomers (b)

(d) Diastereoisomers

O is heated
HOOC
|

OH

CH3
is heated

(c)

CH 3 CHCH 2 COOH is heated

|

(d) CH 3 CHCOOH
CH 2COOH

OH

Cl 105. and

Cl are . isomer

Cl Cl (a) Position (b) Optical 106. The prefixes syn and anti are used to denote (a) Structural isomers (b) Conformational isomers 107. Which will form geometrical isomers

(c) Geometrical (c) Geometrical isomers

(d) Diastereomer
[DPMT 2002]

(d) Optical isomers

Cl

EDUDIGM
Cl

Be sincere, not serious

ISOMERISM
(a) 108. (b) CH 3 CH

NOH

(c)

(d) All of the above

-D-glucose and -D glucose have a specific rotation of becomes 52 o . This process is called (b) Racemisation

112 o and

19 o respectively. In aqueous solution the rotation

(d) Enolisation
[AIEEE 2004]

(a) Inversion 109. Glucose and mannose are

(c) Mutarotation (c) Ketohexoses (b) 2, 3-dichlorobutane (d) 2-hydroxy propanoic acid

(a) Epimers (b) Anomers 110. Which of the following will have a mesoisomer also (a) 2, 3-dichloropentane (c) 2-chlorobutane
CHO

(d) Disaccharides
[AIEEE 2004]

111.

H 3C

C CH 2 CH 3 In this compound chiral carbon has configuration

|

(a) R 112.

(b) S

(c) Both (a) and (b)

(d) None of these

Which is/are correct statements about P and Q P Q (a) P is cis- and Q is trans(b) P is Z and Q is E (d) P and Q are same structure

(c) P is R and Q is S CH 3 C Cl || 113. is Cl C Br (a) trans (b) Z

(c) Both (a) and (b)

(d) None of these

COOH
114.

H HO

1 2 COOH

OH configuration at C1 and C 2 atoms are H

(b) l and l (c) R and R (d) R and S

(a) d and d Et 115.

Me

* H

OH has chiral centre (*). It is

(c) Both (a) and (b) (d) None of these

(a) R (b) S 116. Which are correct statements (a) O and O O (b) CH 3 are enantiomers

Cl
| |

O CH 3
| |

C CH 2 CH 3 and Cl H

C H CH 2CH 3

are same structures

(c) Argol (sodium potassium tartrate) will show optical isomerism (d) CH 3 CHO on reaction with HCN gives racemic mixture 117.
Li / NH 3

A, A is (b) trans-2-butene I and II are (c) Isobutene (d) 1-butene

(a) cis-2-butene 118.

CH3 CH3 H

CH3 H CH3 H (I) (II) (a) Achiral-identical mirror images (c) Geometrical isomer (each separately) 119. Number of chiral carbon atoms in (a) 2 120. C4 H 4 O4 can be (b) 3 Cl CH3 is

(b) Chiral-enantiomers (d) Racemic mixture

(c) 4

(d) 1

EDUDIGM

Be sincere, not serious

ISOMERISM
(a) A cyclic ester (c) gem- , -unsaturated dibasic acid 121. In which case chiral carbon is generated (a) CH 3 COCH 3 (c)
CH 3 COCOOH HCN HCN
H 3O

(b) cis- and trans- dibasic acid (d) All of the above (b) CH 3 CHO (d)
[IIT 1999]
H 3O

HCN

H3O

122. The optically active tartaric acid is named as D (+) tartaric acid because it has a positive (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 when substituted by deuterium 123.

: CH 2

C CH 3 and CH 2
||

C CH 3 are
|

[CBSE PMT 2002]

O:

:O :

(a) Resonating structures (b) Tautomers (c) Geometrical isomers (d) Optical isomers 124. The compound, whose stereo-chemical formula is written below, exhibits x geometrical isomers and y optical isomers

CH 3 C H C

H
. The values of x and y are

CH 2

(a) 4 and 4 (b) 2 and 2 125. Maximum enolisation takes place of (a) CH 3 COCH 3 (b) CH 3 COCH 2CHO
CH3 H H

(c) 2 and 4 (c)

(d) 4 and 2 (d)

CH 3 COCH 2 COCH 3

CH3

126.

H H3C

CH3 H

are

CH3 H3C

(a) Enantiomers (b) Diastereomers (c) Geometrical isomers 127. Which are correct statements (a) Methyl malonic acid is converted into propanoic acid on heating (b) Succinic acid forms succinic anhydride on heating (c) 3-hydroxy propanoic acid forms acrylic acid on heating O (d) CH 3 C CH 2 COOH forms acetone on heating 128. By Fischer projections glyceryl aldehyde is represented as CHO CHO (a)
||

(d) Same structure

C OH CH 2 OH

(b)

C H

CH 2 OH OH

(c) Both (a) and (b)

(d) None of these

129. How many asymmetric carbon atoms are present in (i) 1, 2-dimethyl cyclohexane (ii) 3-methyl cyclopentene (a) Two, one, one (b) One, one, one (c) Two, none,two 130.

(iii) 3-methyl cyclohexene (d) Two, none, one

C 4 H 6 O 4 (A)

C 3 H 6 O 2 (B)

Soda lime

(C) , C is hydrocarbon occupying 0.75 litre per g approximately. Hence A and B are
(b) Succinic acid,succinic anhydride (d) Tartaric acid, propanoic

(a) Methyl malonic acid, propanoic acid (c) Maleic acid, maleic anhydride anhydride 131. Select correct statements (a)

OH

and

OH both give colour with neutral FeCl 3 solution

(b) 2-pentanone and 3-pentanone are position as well as metamers

EDUDIGM

Be sincere, not serious

ISOMERISM
(c) Product formed when benzaldehyde reacts with hydroxylamine shows geometrical isomerism (d) 1, 2-dibromocyclohexane shows geometrical and optical isomerism 132. Which of the following has Z-configuration (i)
CH 3 C H
||

(ii)

CH 3 C H
||

(iii)

Cl C Br
||

(iv)

Cl C
||

Br H

C3 H 7

C2 H 5

C2 H5

C3 H7

(a) Only (i) (b) Only (iii) (c) Both (i) and (iii) (d) Both (i) and (iv) 133. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon. The ester formed will be
[IITS 2003]

(a) Optically active mixture (b) Pure enantiomer (c) Meso compound 134. The process of converting d form to l or vice-versa is known as (a) Walden inversion (b) Resolution (c) Racemisation (d) None of these 135. Which is incorrect about enantiomorphs (a) They have different biological properties (b) They ha ve identical physical properties (c) They can rotate the plane polarised light (d) They have same shape of crystal 136. Diastereomers can be separated by (a) Simple distillation (b) Fractional crystallisation (c) Electrophoresis (d) None of these 137. The least number of carbon atoms for an alkane to show stereoisomerism is (a) 2 (b) 3 138. Which of the following is threo isomer Y Y
| |

(d)

(c) 4

(d) 5

X
|

X X

C
|

C
|

C
|

C Z | A I (a) Only I 139. In the reaction CH 3 CHO

(a) Meso compound

Z C X | A II (b) Only II

HCN

Z C X | A III (c) Only III (d) All of the above CH 3 CH (OH )CN a chiral centre is produced. Thus product would be
[CBSE 1995; Pb. PMT 1998]

(b) Racemic mixture

(c) Laevorotatory

(d) Dextrorotatory (d) Two asymmetric C-atoms

[IIT Screening 2002]

140. meso-Tartaric acid is optically inactive due to the presence of (a) Molecular symmetry (b) Molecular asymmetry (c) External compensation 141. Which of the following compound exhibit stereoisomerism (a) 2-Methylbutene-1 (b) 3-Methylbutyne-3 (c) 3-Methylbutanoic acid 142. Which of the following pairs of compounds are enantiomers
CH 3 CH 3 H HO and OH HO CH 3 CH 3 H HO CH 3 OH HO and H HO CH 3 CH 3 CH 3 H H H HO CH 3 H H CH 3 HO H H HO CH 3 CH 3 OH H and H H OH HO and H H

(d) 2-Methylbutanoic acid

[CBSE 2003]

CH 3 H OH CH 3 CH 3 OH OH CH 3

(a)

(b)

(c)

(d)

143. The correct statement about the compounds A, B and C is

H H

COOCH 3 OH OH COOH (A)

COOH H H OH OH COOCH 3 (B) H HO

COOH OH H COOCH 3 (C)

[IIT 1997]

(a) A and B are identical (b) A and B are diastereomers (c) A and C are enantiomers (d) A and B are enantiomers 144. Which of the following may exist in enantiomorphs [CBSE 1988] CH 3 NH 2 NH 2 (a) CH 3
|

CH COOH

(b) CH 2

CHCH 2 CH 2 CH 3

(c)

CH 3

CH CH 3

(d) CH 3

CH 2

CH CH 3

145. Hydrogenation of the adjoining compound in the presence of poisoned palladium catalyst gives

[IIT Screening 2001]

Me
EDUDIGM Me H Be sincere, not serious

Me

ISOMERISM

(a) An optically active compound (c) A racemic mixture 146. Which of the following contains asymmetric centre (a) 2-butene (b) 2, 2-dimethylpropane 147. Which of the following is expected to be optically active (a) (CH 3 )4 C (b) C2 H 5 CH (CH 3 )C3 H7 148. Which compound does not show geometrical isomerism

(b) An optically inactive compound (d) A diastereomeric mixture

[CPMT 1996]

(c) 2-hexyne (c)

(d) Lactic acid

[JIPMER 1997]

(C2 H 5 )2 CHCH 3

(d) CH 3 CH

CHCH 3
[RPMT 1997]

(a) 2-butene (b) 2-pentene (c) 2, 3-dibromo-2-butene (d) 2-methyl propene 149. The optically active tartaric acid is named as D (+) tartaric acid because it has a positive [IIT 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 150. Which one of the following is an optically active compound (a) n-propanol (b) 2-chlorobutane
[CBSE 1988; DPMT 1983]

(c) n-butanol

(d) 4-hydroxyheptane

151. 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 CH3 152. H3C (a) 2 OH (b) 5 (c) 6 (d) 3
[CBSE 1988; DPMT 1983; KCET 2002]

(d) Oxygen of the hydroxyl groups . How many structures of F is possible (Geometrical)
[IIT Screening 2003]

153. Separating of d- and l- enantiomorphs from a racemic mixture is called (a) Resolution (b) Dehydration (c) Rotation 154. Meso-tartaric acid is (a) Optically inactive (c) Optically inactive due to external compensation 155. 1, 2-dichloroethene shows (a) Geometrical isomerism (b) Optical isomerism 156. Which of the following does not show geometrical isomerism (a) 1, 2-dichloro-1-pentene (b) 1, 3-dichloro-2-pentene 157. Methyl acetate and propionic acid are (a) Functional isomer (b) Structural isomer 158. Lactic acid shows which type of isomerism (a) Geometrical isomerism (b) Tautomerism (a) Chain isomers (a) 1 (a) Enantiomers (a) 1-chlorobutane (a) CH 3 CH (OH )CO 2 H (b) Optical isomers (b) 2 (b) Tautomers (b) 2-chlorobutane (b) CH 3 CH 2 CH (CH 3 )CH 2 OH (c) Optical isomerism (c) Cis-trans isomers (c) 3 (c) Diastereoisomers

(d) Dehydrohalogenation
[BHU 2001]

(b) Optically active because of molecular symmetry (d) Optically active because of asymmetric carbon atom
[RPET 1999]

(c) Ring-chain isomerism (c) 1, 1-dichloro-1-pentene (c) Stereoisomer

(d) Resonance
[AIEEE 2002]

(d) 1, 4-dichloro-2-pentene
[RPMT 2002]

(d) Geometrical isomer

[CPMT 1987; MP PMT 1987]

(d) Metamerism (d) Position isomers

[Roorkee 1992]

159. On bromination, propionic acid yields two isomeric 2-bromopropionic acids. This pair is an important example of[BHU 2000] 160. The maximum number of stereoisomers possible for 2-hydroxy-2-methyl butanoic acid is (d) 4
[MH CET 1999]

161. d-tartaric acid and l-tartaric acid are 162. Which of the following compounds does not contain a chiral carbon (c) 3-chloro-3-methylhexane (d) 2-butanol 163. Which of the following compounds may not exist as enantiomers (c)

(d) Structural isomers

[CPMT 1987]

C6 H 5 CH 2 CH 3

(d) C6 H 5 CHClCH 3
[DCE 1999]

164. Which compound is optically active

EDUDIGM

Be sincere, not serious

ISOMERISM
(a) 4-chloro-1-hydroxy butane (c) Secondary butyl amine 165. Which compound shows cis-trans isomerism (a) 1-butene 166. Which compound is chiral (a) Butane (a) CH 3 CH 2 COOH (a) 4 (a) 2-butene (b) 1-chloro-2-methyl butane (b) CH 3 CHOHCOOH (b) 3 (b) 2-butyne (c) 2-methyl butane (c) 167. Which of the following compounds exhibit optical isomerism (b) 2-propene (c) 2-butene (d) Benzene
[RPMT 2002]

(b) 3o-butyl alcohol (d) n-butyl alcohol

[CPMT 2002]

(d) 2-methyl propane (d) CH 3 CHOHCH 3

[BHU 1983; AFMC 1990; CPMT 1993; MP PMT 1999, 2000]

CH 3 CH 2 CH 2OH CH

168. The number of geometrical isomers in case of a compound with the structure CH 3 (c) 2 (c) 2-butanol 169. Geometrical isomerism is shown by

CH

CH

CH

C2 H 5 is [NCERT 1980]

(d) 5 (d) Butanal

[IIT 1983; CPMT 1990, 94; CBSE 1992; MP PET 1997; AMU (Engg.) 1999]

170. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon. The ester formed will be
[IIT Screening 2003]

(a) Optically active mixture (a) 2-butene (a) Maleic-fumaric acid (a) Their physical state

(b)

Pure enantiomer (c) 1-phenylpropene (c) Malonic-succinic acid (b) Their reduction products

(c) Meso compound (d) 2-methyl-2-butene

(d)
[IIT 1998]

171. Which of the following compounds will show geometrical isomerism (b) Propene (b) Lactic-tartaric acid 172. Which pair show cis-trans isomerism 173. The isomeric cis-2-butene and trans-2-butene can be distinguished on the basis of (c) The products they give on ozonolysis 174. Number of optical isomers of lactic acid are (a) 1 (a) (b) 2 (b) CH 3 CH 2 CHDCl (c) 3 (c) (d) 4 175. Which of the following compounds is not chi ral (d) The products they give on addition to bromine

[RPET 1999]

(d) Crotonic-acrylic acid

[NTSE 1991]

[CBSE 1998]

DCH 2 CH 2 CH 2 Cl

CH 3 CHDCH 2CH 2Cl

(d) CH 2 CHClCH 2 D
[CPMT 1999; UPSEAT 1999, 2000, 02]

176. What is the possible number of optical isomers for a compound containing 2 -dissimilar asymmetric carbon atom (a) 2 (a) 1-butanol (a) 3-chloropentane (b) 4 (b) 2-butanol (b) 2-chlorobutane (c) 6 (c) 3-butanol (c) 2-chloropropane (d) 8
[UPSEAT 1999]

177. Which of the following compounds whi ch is an optically active compound (d) 4-heptanol 178. Optically active compound is 179. The most stable conformation of n-butane is (a) Skew boat (b) Eclipsed (c) Gauche 180. Isomerism due to rotation round single bond of carbon-carbon is (a) Conformation (b) Enantiomerism 181. Which statement is true for cyclohexane (a) It has two possible isomers (c) Boat conformation is most stable kJ/mol 182. What are the type of isomers in following pairs H CH3 H H CH3 H (c) Diastereo isomerism (d) Staggered

[UPSEAT 2002]

(d) None of these

[CBSE 1997] [UPSEAT 2003]

(d) Position isomerism

[MP PET 1996]

(b) It has three conformations (d) Chair and boat conformations differ in energy by 44

and
H H (I) (a) Conformers (b) Position H CH3 H

CH3 (II ) (c) Optical

(d) Geometrical

EDUDIGM

Be sincere, not serious

ISOMERISM
183. Which type of conformation is shown by I and II H H H H H H

HH H H H
(II ) (b) II is eclipsed, I is staggered (d) Both are staggered
[CBSE 2000; IIT 2004]

H (I) (a) I is eclipsed, II is staggered (c) Both are eclipsed

184. The dihedral angle between the hydrogen atoms of the two methyl groups in staggered conformation of ethane is (a) 120 (b) 60 (c) 180 185. Which of the following molecule can exhibit conformational isomers (a) C 2 H 6 (b) H 2 O 2 (c) NH 2 NH 2
o o o

(d) 90

(d) All of the above

186. Least hindered rotation about carbon-carbon bond is observed in [RPMT 2000] (a) Ethane (b) Ethylene (c) Ethyne (d) Hexachloroethane 187. In ethane and cyclohexane which one of the following pairs of conformations are more stable (a) Eclipsed and chair conformations (b) Staggered and chair conformations (c) Staggered and boat conformations (d) Eclipsed and boat conformations 188. The isomers which can be converted into another forms by rotation of the molecules around single bond are [AIIMS 1997] (a) Geometrical isomers (b) Conformers (c) Enantiomers (d) Diastereomers 189. Which one of the following represents eclipsed form of ethane H H H H H H H H H H (a) (b) (c) (d) None of these H H H H 190. Which are the staggered forms of ethane H H H H H

H
H H C H H H H

HH

H
C

C H
H H H (c) (2) and (4) C

H H

(1)

H H

(2)

(3)

(4) H
(d) (1) and (3)
[CPMT 1992]

(a) (1) and (4) 191. Example of chlorinolysis is (a) CH 2 (c)

(b) (3) and (4)

CH 2

Cl 2

C2 H 4 Cl2
HCOONa 3 NaCl 2 H 2O

(b) CCl 4 (d) C3 H 8

H 2O
Cl 2

COCl 2

2 HCl

CHCl 3

4 NaOH

CCl 4

C2Cl6

8 HCl
CH 2 (III) when subjected to

192. What is the order of reactivity of the alkenes (CH 3 )2 C

CH 2 (I) , CH 3 CH

CH 2 (II) and CH 2

acid-catalysed hydration (a) I > II > III (b) I > III > II (c) III > II > II 193. The most unlikely representation of resonance structures of p-nitrophenoxide ion is O + O O + O O + O N N N (a) (b) (c)

(d) II > I > III

O
(d)

H 3C
194. The compounds

H C C CH 3
and

H 3C C H C

CH 3
can be distinguished by their

H
(a) Chlorinated products

H
(b) Products formed by addition of bromine

EDUDIGM

Be sincere, not serious

ISOMERISM
(c) Reaction with H 2 / Ni (a) (d) None of these

195. During elimination reactions, the hybrid state of carbon atoms involved in change shows

sp 3 to sp 2 nature

(b) sp 2 to sp nature (d) Either of the above

[MP PMT 1998]

(c) No change in hybridised state

196. An unknown compound A has a molecular formula C 4 H 6 . When A is treated with an excess of Br2 a new substance B with formula C4 H 6 Br4 is formed. A forms a white ppt. with ammoniacal silver nitrate solution. A may be (a) But-1-yne (b) But-2-yne (c) But-1-ene (d) But-2-ene

EDUDIGM

Be sincere, not serious