Isomerism
NCERT CORNER
NeERT Text Bas.edObjective and Exemplar Problems
1. In which of the following, functional group isomerism
is not possible?
(a) Alcohols
(b) Aldehydes
Cc) Alkyl halides
(d) Cyanides
Solution
1. (c) Alkyl halides
do, not show functional
group
isomerism.
Assertion~Reason Type Problems
In the following questions a statement of
Assertion (A) followed
by a statement
of
Reason (R) is given. Choose the correct option
out of the choices given below each question.
1. Assertion (A): Pent- 1- ene and pent- 2- ene are
position isomers.
Reason (R): Position isomers differ in the position of
functional group or a substituent.
(a) Both A and R are correct and R is the correct
explanation of A.
(b) Both A and R are correct but R is not the correct
explanation of A.
(c) Both A and R are not correct.
(d) A is correct but R is not correct.
Level 1 : Conceptual Objective Problems,
Structural Isomerism
10. How many positional isomers are possible for
1. How many dibromobenzenes are possible?
(a) 1
(c) 3
LCI
lS:2J?
Cb) 2
(d) 4
2. The number of all the possible structural isomers of
butane is:
(a) 2
(c) 6
CH3 -
CA)
(d)
°II
C -CH3
0 0
and
°
(e)
°
(b)
9 0
OH
. (b)
; Number of positional isoiners for the
N02
.
compound given are :
4
Cb) 5
(c) 6
(d) 7
(a)
(b) 4
Cc) 5 .
Cd) 6
(B)
(a) chain isomers
(b) positional isomers
(c) metamers
(d) functional isomers
n;
(A) and (B) are:
OH OH
OH
(B)
(A)
(b) positional isomers
(a) chain isomers
(d) functional isomers
(c) metamers
7. How many distinct terminal alkynes are possible for a
compound having molecular formula CsHs?
CI
15.&Cl A ;
(A) and (B) are:
(b) 2
«n
Cc) 3
4
8. How many distinct internal alkynes may exist with a
molecular formula ofC6HlO?
'
Ca) 1
Cb) 2
(c) 3
4
«n
~Cl
(A)
(a) chain isomers
by the
.
CB)
(b)
(c) metamers
16. CH3 -CH2
(e) 5
9. The number of ether me tamers represented
molecular formula C4H100 is:
positional isomers
(d) functional isomers
-CH2
-C02H
(A)
(A) and (B) are:
CH3 -CH-CH3
I
C02H
(B)
(b) 2
Cd) 4
(A) and (B) are:
~;
Cd) 6
(a) 3
(a) 1
Cc) 3
12.
14. ,,<OH
A
6. How many distinct terminal alkenes are possible for a
compound having molecular formula C6H 12 ?
1
NO
CA)
5. How many distinct terminal alkynes are possible for a
compound having molecular formula C 6H 10 ?
(a)
«n
13.~
and
(a) 3
(c) 5
(b) 3
5
CH3
and
0 0
.
2.
metamers
OH
«n
(a) 2
(c) 4
CB)
4. Which of the following pairs of structures does not
represent isomers?
(a)
(b) 3
5
@(?
Relation between (A) and (B) is :
(a) chain isomers
(b) positional isomers
Cc) functional isomers
2
Cc) 4
11. How many positional isomers are possible for
(b) 4
(d) 5
3. CH3 -CH2-CHO;
(a)
(a) chain isomers
(b) positional isomers
Cc) functional isomers
«n metamers
OH
17.
25. How many cyclic structural isomers are possible for
A ;(A) and (B) are:
/'-..,/OH
(A)
CSHlO ?
(a) 4
(B)
(a) chain isomers
(b) functional isomers
(c) metamers
(d)
~O
18.~
°
(A)
(b) 5
(d) 7
Cc) 6
positional isomers
; (A) and (B) are:
26. How many structural isomers of C6H 12 may contain
3-membered ring?
(a) 4
(b) 5
(c) 6
Cd) 7
27. How many structural isomer. of C6H12 may contain
4-membered ring?
.
(B)
(a) chain isomers
(b) functional isomers
(a) 3
(c) 5
(c) metamers
(d) positional isomers
28. How many
19. /'-..,/OH
~OH
; CA) and (B) are:
on
CA)
(a) chain isomers
(b) functional isomers
(c) metamers
(d) homologues
20. Which of the following pairs represent isomers?
(a) CH3 -CH3,
CH3 -CH2 -CH3
(b) H2C = CH-OH,
CH3 -0
-CH3
(c) CH3 -CH2
-CH3'
CH3 -
-CH2
CH -CH3
I
CH3
(d) All of these
21. Which of the following represent
(b) 4
(d) 6
ketones
formula C6H120 ?
are possible with molecular
(b) 6
(a) 5
(c) 7
Cd) 8
29. What
type of isomers
CH3CH2CH20H are?
CH3CH20CH3
(a) Constitutional
(b) Symmetrical
(c) Configurational
(e) Stereochemical
(d) Conformational
arid
30. What is the relationship between the structures shown
below?
a pair of chain
isomers?
.
(a) n-pentane, Iso-pentane
Br
Hand
(b) n-pentane, Neo-pentane
(a) Not isomers
(c) Iso-pentane, Nee-pentane
(b) Constitutional isomers
(d) All of these
22. Total number of stereoisomers for .2,3-dichlorobutane
is:
23. CH3 -CH2
-CHz
-C
(A)
= N;
CH3-CH-CH3
Relation between (A) and (B) is:
(a) chain isomers
(b) positional isomers
24. CH3 -O-CH2
-CH2
(A)
(d) me tamers
-CH3;
CH3 -CH2
-O-CH2
-CH3
(B)
Relations between CA)and (B) is:
(a) chain isomers
(b) positional isomers
(c) functional isomers
(d) metamers
31. What is the relationship between the structures shown
below?
I
CN
(B)
(c) functional isomers
(d) Configurational isomers
Ce) Enantiomers
(b) 4
(d) 6
(a) 3
(c) 5
(c) Conformational isomers
~and
Br
~
H
Br
Br
(a) Diastereomers
(b) Constitutional isomers
(c) Conformational isomers
(d) Configurational isomers
(e) Enantiomers
32.CH3CHOHCH2CHO
constitute a pair of :
Ca) Position isomers
(c) Optical isomers
and
CH3CH2CH2COOH
(b) Metamers
(d) Functional isomers
( 40 )
,
33. The minimum number of carbon atoms present in an
organic compound to show chain isomerism is :
(a) 2
Cc) 5
Cb) 3
Ca) 2
Cc) 4
41. The minimum number of carbon atoms in ketone to
show metamerism:
(d) 4
34. The minimum number of carbon atoms present in an
organic compound to show position isomerism is:
(a) 3
.
«n 5
35. Which of the following compound is isomeric with
propanoic acid:
(a) CH3 - C-OC2HS
II
o
-C-H
OH
0
I
H*Me
Br
(b) Position isomers
(c) Chain isomers
Cd) Metamers
II
(a) 2-methoxy butane
Cb) I-methoxy butane
Cc) ethyl n-propyl ether
(d) n-pentyl alcohol
H*Me
H
H
H
45. The number of primary, secondary and tertiary amines
possible with the molecular formula C3H9Ns given by
the set:
H
Cl
CH2Cl
(a) Enantiomers
(c) Conformers
37. CH3 -NH-C2Hs
of isomerism:
(d) None
and CCH3hN show which type
I
=0
and
-CH2
(c) 2, 1, 1
(d) 3,0, 1
(a) 10
(b) 11
Cc) 12
(d) 13
(a) 4
(b) 5
(c) 6
(d) 7
H
48.
I
H
H
H
Cl
(b) 1,2, 1
47. The number of isomers ofC3HsBr3 is:
(b) Functional
(d) None
-C
(a) 1,2,2
46. The number of isomers ofCsH10 is:
(b) Position isomers
(a) Position
(c) Chain
38. CH3 -CH-CH2
(b) 4
Cc) 5
Cd) 6
44. Which of the following is not a metamer of CsH 120 :
Me
H
- C-Clare
II .
constitute a pair of:
o
(a) Position isomers
Cl
HLJCl
CI
CI
r=:
H
The above compounds differ in :
(a) configuration
(c) structure
(b) conformation
(d) chirality
49. How many primary amines are possible for the
(b) Metamers
formula C4H 11N ?
(a) 2
(c) Optical isomers
(d) Functional group isomers
39. The minimum number pf carbon atoms in ketone to
show position isomerism:
Cc) 5
(a) Functional isomers
43. Number is structural isomers ofC6H14 is:
(c) CH3 -CH(OH)-CH3
Cd) CH30-CH2
-CH20H
36. The pair of structures represents:
(a) 3
I
(a) 3
(b) CH2-CH2
CH3 -CH2
(b) 4
(d) 6
42. BrCH2 -CH2 -CH =0 and CH3 -CH2 - C =0:
(b) 4
Cc) 2
(a) 3
(c) 5
(b) 4
(d) 6
40. How mmany isomers of CSHllOH will be primary
alchols:
(c)
4
50. The
compounds
CH30CH2CH2CH3 are:
(a) enantiomers
(b) geometrical isomers
Cc) Metamers
(d) conformational isomers
(b) 3
(d) 5
and
41
51. C4H602
does not represent:
(Hi) CH 3 - CH = CH - CH = CH - CH 3
.. The numbers of possible geometric isomers for the
above compounds respectively are:
(a) A diketone
(b) A compound with two aldehyde
(c) An alkenoic acid
Cd) An alkanoic acid
52. Which of the following statements is/are correct?
(a) Metamerism belongs to the category of structural
isomerism
(b) Tautomeric
structures
are the resonating
structures of a molecule
(c) Keto form is always more stable than the enol
form
(d) geometrical isomerism is shown only by alkenes
53. Only two isomeric
possible for:
monochloro
derivatives
are
(a) 0, 2,4
(b) 2, 2, 4
(c) 0, 3, 3
(d) 0,2,3
58. Which of following compound
geometrical isomerism?
(b)
0=<>
(c)
Cd)~
59. Which of the following compound show cis and trans
isomerism?
=CH-Cl
(el
Geometrical Isomerism.
54. Determine the double bond stereochemistry
for the following molecules.
(E or Z)
F)=(H3
60. Which of the following compound
geometrical isomerism ?
CH3
CH
(a)
'C=C=C"""""
3
H/
(b) CH3 -C
H
A
(a) A: E; B: E
(b) A: Z; B: Z
(c) A: E; B: Z
(d) A:Z;B:E
55. What is the IUPAC name for the following compound?
H)C=C<H
CH3
show
6
(c) benzene
(d) 2-methylpentane
H3C
not
<><> <><>
(a)
(a) CI-CH
(a) n-butane
(b) 2,4-dimethylpentane
will
<H
C=C
H/
(c)
(a) cis, trans-Z, 4-heptadiene
(c) trans, trans-2,4-heptadiene
'H
=C-CH3
(d) All of these
61. How many geometrical isomer are possible for the
given compound ?
°
0:;
(b) 1
(d) 3
(a)
(c) 2
62. How many geometrical isomers are possible for
«n
2E, 4E-2,4-heptadiene
56. Geometrical isomerism results because the molecule:
(a) rotates the plane of polarized light
(b) has a plane of symmetry
(c) has a centre of symmetry
(d) has two dissimilar groups attached to both ends of
double bond
57. (i) CH2 =CH-CH2
-CH =CH2
(ii) CH2 =CH-CH
= CH-CH3
show
CH .
H
3'C~C"""""
. CI/
'H
CH2CH3
(b) cis, cis-2,4-heptadiene
not
<>
°
(a)
(c) 2
Cb) 1
«o 3
63. How many geometrical isomers are possible for
Br
A
B~Br
?
r 42 X~~~-~~--~~~~~~ __
~~~~_~~=~~~~~~~
(a) 0
(c) 2
(b) 1
(a) Optical
(b) Functional
Cd) 3
(c) Metamerism
(d) .Geometrical
64. How many geometrical isomers are possible for
CH3 - CH = C = CH - CH = CH - CH3?
(a) 0
(b) 1
Cc) 2
Cd) 3
65. How many geometrical isomers are possible for
CH3 - CH = C = C = C = CH - CH = CH- CH3
?
(a) 1
(c) 3
(yCl
.
Br)c
<CHCCH3)z
(b) HOCH
=C
CHz-CH3
z
Cd) All the above
66. Which of the following compound will not show
geometrical isomers ?
(a) ~
(a) H3~)c=c<~zHs
(c) Bl')c=C<H
Cl
D
(b) 2
(d) 4
rl<Cl
73. Which of the following has E-configuration:
74. Which of the following has Z-configuration:
(a)
(b) ~
H3C'C=C/CHO
H/
'CH20H
HsCz, _C/OH
(b) H3C/C'CH20H
(c) (XCI
(d) All of these
C1
"1"
ibl e lor
C
67. How many geometnca Isomers are POSSI
CH3~CH3?
H~H
"
(a) 2
(c) 4
(d) All of these
(b) 3
(d) 6
68. How many geometrical isomers are possible for
CH3 -CH =CH-CH=CH-Cl?
(a) 2
(c) 4
(c) HOH2C"C=C/CH3
HzN/
"CHCCH3h
(b) 3
Cd) 5
69. How many geometrical isomers are possible for
Ph-CH=CH-CH
=CH-Ph?
75. Which is a pair of geometrical isomer:
ci;
/Br
Cl'C=C/Br
H/C=C"Br
H/
'CH3
(I)
(II)
CI'C=C/H
Br/
"H
H,
/Br
C=C
Cl/
"CH3
(III)
(IV)
2
(b) 3
Ca) I and II
(b) I and III
Cc) 4
Cd) 5
(c) II and IV
Cd) III and IV
(a)
70. How many geometrical isomers are possible for
~?
Me~.
(a) 0
(c) 2
(b) 1
(d) 3
71. What is the relationship
compounds?
CH3)C=C<H
H
76. The IUPACname of compound:
and
Br
between
H
CH(
M)
the following
C-C<H
-
Br
(a) Configurational isomers
Cb) Conformational isomers
(c) Constitutional isomers
(d) Structural isomers
72. The isomerism shown by H3C-89>-CH=N-O~iS:
C
(a) (Z)- 4,6,7-Trimethyl hept- 4 - en-3-one
(b) (E)- 4,6-Dimethyl oct-4-en-3-one
(c) (Z)- 4,6- Dimethyl oct- 4 - en-3-one
(d) (E)- 4,6-Dimethyl oct-4-en-3-one
77. Which can show Geometrical isomerism:
CH3'C=C/H
Cb) H'C_C/CH3
(a) CH{
'H
tV - "H
78. Which is a pair of geometrical isomers:
cr.'C=C /Me
Br,
/H
(a)
and
'C=C
Br/
"H
Cl/
"Me
85. Which Newman projection formula does not represent
the following compound?
ry---~-~---~;l
and
I
I
I
I
~-------- -- .'
...
H
Cl
Br
Cc) band
Cd)
Me
Ca)
Br
Cb)
Cl
Me
Ph
"C=C/
CH/3
"Me
H
H
and
M~
H
.
Me
Cl
H
79. Geometrical isomerism is shown by:
1"
/CH3
Cb)
/C=C."H
CH3
"
H
Cc)
H
(a) only sp-hybridized carbons atoms
CI
H
H;$tCH
(b) only sp2-hybridized carbon atoms
(a)
(d) Sp,Sp2 and sp3-hybridized carbon atoms
compounds
(a) CH2 = CHBr
(b) CH2 =CBr2
(c) ClCH =CHBr
(d) Br2C=CCl2
Newman
3
(c) both sp and Sp2 hybridized carbon atoms
81. Which of the following
geometrical isomerism ?
Cd)
86. Choose the correct
2-methylpentane.
H
80. The compound 1,2-butadiene has:
Me
Me
H
~
Me
H
CH3
(b)
projection
H:$:~
CH3
H
CH2CH3
Cc)
H:$:H
H
CH2CH3
H;$tCH
H
CH3
Cd)
CH3
Cr-»>:
3
H .
CH2CH3
H
87. Identify conformer of 2-methyl pentane:
(a) 2
Cb) 4
(c) 6
(d) 8
·83. Which of the following compounds
will not show
geometrical isomerism ?
(c) 1-phenylpropene
HJtrCH3
Cc) 4-phenyl-1-butene
Cd) Pentene
(b)
H
H
CH2CH3
(d) 2-bromo-2-butene
will exhibit
H
(a) 1-phenyl-2-butene
(b) 3-phenyl-1-butene
H
(a)
(b) propene
84. Which of the following compounds
geometrical isomerism ?
for
displays
82. The number of cis-trans isomer possible for the
following compound :
(a) 2-butene
HH
H
(c)
Cd)
H
( 44
OH
H
z
H
88.
(III)
H
H
H
Above gauche form is stable when Z is:
(a) -F
Cc) -OCH3
H
(b) -OH
H
(d) All of these
Ell
NMe3
(N)
z
89.
H
H
H
H
H
H
Above gauche form is stable when Z is:
(a) -CH3
(b) -Et
(c) -C-OEt
(d)
o
II
-Ph
90. The eclipsed and staggered forms of ethane are said to
differ in:
(b)
Cc) conformation
Cd) constitution
91. Which of the following is the staggered conformation
for rotation about the C 1 - C 2 bond in the following
structure?
CH3
I
CH3CHCH2CH3
234
H
(b) II
.(a) I
(e) V
configuration
(a) molecular formula
(c) III
(d)
IV
92. Which of the following best explains the reason for the
relative stabilities of the conformers shown?
CH3
H
H
H
(I)
(II)
H
H
H
H
CH3
CH~CH2CH3
(a) I has more torsional strain.
(I)
(b) I has more steric strain
H
H
H
(d) II has more steric strain
CH3
CH3'KX'CH2CH3
(II)
.A0
CH3
H
(c) II has more torsional strain
93. Rotational angle require to get maximum stable
conformer from minimum stable conformer in
n-butane is :
0
Cb) 180
(c) 120
Cd) 240
Ca) 360
0
H
0
0
94. Isomers which can be interconverted through rotation
around a single bond are:
(a) Conformers
(b) Diasereomers
(c) Enantiomers
, (d) Positional isomers
45
C
95. In the given conformation, if C 2 is rotated about
C2 3 bond anticlockwise by an angle of 120 then
the conformation obtained is :
0
4
Cc) diastereomers
(d) identical molecules
100. Which of the following compound is chiral ?
·0
CH3
.
OOOH
.
(a) ~
(b)
H
H
.,
FyfyCH
H
3
lCH3
F
(d) CI••••. C .•••• Br
(c) CH3~F
I
(a) fully eclipsed conformation
H
(b) partially eclipsed conformation
H
101. Identify meso compound:
(c) gauche conformation
(d) staggered conformation
i
HyCl
3
H+CI
96. In the Newman projection for 2,2-dimethylbutane
(a)
Cl---i-H
(b)
~.
Cl
x
H
CH3
ltJ '
CH3
Cl
(c)
y
Cd)
X and Yare can respectively by:
(a) Hand H
(b) Hand C2HS
(c) C2HS and H
(d) propane
Cl
102. In which of the following compound have plane of
symmetry ?
Optical-Isomerism
97. Total number
of stereoisomers
2-~romo-3-chlorobutane is:
Ca) 3
Cb) 4
(c) 5
98. What is the relationship between
and cis-2-butene?
possible
CH3p:CH3
for
Cd) 6
trans-2-butene
(a)
(c)
(c) Enantiomers
lY
,~
0
'~CI
between
the
two
DCJ;
103·0
CH3
CH3
C1
(b) Constitutional isomers
o
(b)
CH3~~·
(a) Unrelated compounds
(d) Diastereomers
99. Determine the relationship
molecules shown ..
Cl~Cl
CA)
(B)
Relation between (A) and (B) is:
.LJ
46
104. Which of the following is chiral compound?
(a)ef
~)C(
,,,,,,,Q
0::
(e)
(d)
105. Which of the following compound is achiral although
it contain chiral center?
108.: r2~:;
Number of plane of symmetry in given
C02H
compound is:
(a) 1
(c) 3
(b) 2
(d) 4
109.S!oH
:z
(a) (Number of chiral center)
~
n~~
(d)
(0)
o
106. Which of the following compound is achiral ?
(a)
(e)
o
~""(O~
(b)
~(b)
"-AC02H
01
~~~"(O
;::1
(Number of chiral center)
sum of(a+b=?):
(a) 3
(c) 5
(b) 4
(d) 6
110. Which of the following are meso compound?
Br
H~~H
Br
(a) H \\\\\\H'IIII/
H
(b) HO~H
CH3 CH3
CH20H
107. Which of the following compound is resolvable?
N02 S03H
(a)#
N02
(e)
~H3
(d) All of these
~OH
S03H
111. For the following compound number of chiral centers
and stereoisomers are:
CH2 -C02H
I
CH-C02H
HO
(c)@-@
(d)
I
CH-C02H
(a) 1, 2
(b) 2,4
(c) 2, 3
Cd) 3,8
112. Which of following compound has one of the
stereo isomers as a meso compound ?
ca)9
~)Q
47
Cd)
ce)~
(5
119. Number of chiral centers present in tartaric acid
:r~:
is:
COzH
How many
compound?
chiral center
(a) 1
(c) 3
are present
in· above.
(b) 2
(a) 1
(c) 3
(d) 4
120. What is the relationship
compounds?
(b) 2
(d) 4
between
the following
!H3
114. What is the optical rotation of (A) ?
and
H ••••..,~CI
O~CI
~,(O)
Clw
(A)
(a) +500
(c) 00
(a) Constitutional isomers
(b) -SOD
Cb) Enantiomers
(d) 100
(c) Diastereomers
0
(d) Conformational isomers
.~CH3
11S.C):)
Ce) Superimposable without bond rotation
Number of chiral center present in above compounds
are:
(a)
0, 1
Cb) 0,2
Cc) 0,3
(d)
1,2
o
121. Which of the following compounds is never chiral?
Ca) 2,3-dibromobutane
(b) 1,3-dibromobutane
(c) 1,2-dichlorobutane
(d) 1,4-dibromobutane
116.(x:
122. Which of the following compounds is chiral?
Number of chiral center present in above compounds
are:
(a)
H
::t= ~):::t::
(a) 1,2
(b) 2,2
(c) 2, 1
Cd) 2,3
H
H
H
CH3
CH3
I
CH3-C-D
I
T
Ce)
Number of chiral center present are:
(a) 0,
°
°
Cb) 1,
Cd) 2,2
(c) 1, 1
118.
H
Br--O--
CI
Number of stereocenters in the compound given are:
(a)
°
Cc) 2
(b) 1
Cd) 3
::t=
Cd)
:::t=
CH3
CH3
.123. What is the relationship between the structures shown
below?
CI
CI
H+Br
CH3
(a) enantiomers
(b) diastereomers
and
Br+CH3
H
48
(c) configurational isomers
(d) identical compounds
124. Which of the following compounds has an 5
configuration?
Cl
CH Cl
2
(a) H+CH3
(c) Constitutional isomers
Cd) Conformational isomers
128. What is the relationship between the following
compounds?
CH3
CH3
Cb) H+CH3
CH2Cl
Cl+H
Cl
(d) CH3+Cl
(c) CH3+H
CH2Cl
Cl .
125. Which of the following compounds has an R
configuration?
H
(a) CH3CH2+
Br
CH=CH2
Cl+H
Cl+H
H
CH2Cl
CH3
Enantiomers
(b) Diastereomers
(c) Constitutional isomers
(d) Conformational isomers
129. How many diastereomers exist for the compound
below?
C02H
(a)
H~*~:
CH=CH2
(b) Br+H
CH2CH3
CH20H
oo
2
(b) 4
(c) 6
Cd) 7
130. Which of the following is a meso compound?
CH2CH3
(c) Br+CH
'.
H+Cl
and
. CH2
HtCH3Cl
H
.
(a)
CH2CH3
H tCH3Cl
(b)
H
Cl
Cl
H
(d) CH2=CH+H
CH3
Br
126. Which of the following groups has the highest priority
using the Cahn, Ingold, Prelog rules?
o
II
°II
(a) -C-OH
(b)
-C-H
Cc)·-OH
Cd) -O-CH3
127. What is the relationship between the following
compounds?
CH3
:i':1
and
n» Diastereomers
CH3
CH3
CI
CI
(c) Ht
H
Cd)Ht
Cl
Cl
H
CH2CH3
CH2CH3
131. What is the configuration of the following compound?
CH3
H+Cl
H+Cl
Cl+H
Cl+H
CH2CH3
CH3
(a) Enantiomers
CH3
Ca) 25,3R
(c) 2S,35
(b) 3R,35
Cd) 2R,3R
-------------~------------~-----------------------------
49
132. In the Fischer projection below, what are the
configurations of the two asymmetric centers?
C02H
:+::3
(b) 6
«n 12
(a) 0
(d) 2S,3S
133. How many chiral carbon centers are in the following
molecule?
CH3
~CH3
\H
(a) 0
Cc) 2
(a) 4
(c) 8
exist for the compound
BrCH2CH(CH3)CH2CH3
(b) 2R,3S
o
Total number of stereoisomers are:
138. How many stereoisomers
given below?
CH2CH20H
(a) 2R,3R
(c) 2S,3R
(b) 1
Cd) 3
134. How many stereo isomers are there for the following
structure?
(b) 1
(c)
139. How many stereoisomers
given below?
2
(d) 4
exist for the compound
CH3CHCICH2CHCICH3
«n
(a) 0
(b) 1
Cc) 2
3
140. The simplest alkanol exhibiting optical activity is :
(a) n-butyl chloride
(b) Isobutyl chloride
(c) s-butyl chloride
(d) r-butyl chloride
H3C) _ /H
141. HSC2 C-C)c<H
H C
3
OHExhibits:
CO
(a) Tautomerism
(b) Optical isomerism
Cc) Geometrical isomerism
(a) 1
(c) 3
Cd) Geometrical and optical isomerism
(b) 2
(d) 4
135. Shikimic acid is an important natural product. How
many stereoisomers are possible for shikimic acid?
o
142. Meso-tartaric acid
I:=i=~:]
~
Ca) Optically active
HO~OH
is:
COOH
(b) Optically inactive
HO~
(c) G.!.
OH
Cd) Structural isomer
(a) 16
(c) 4
(b) 8
(d) 2
143. Which is optically active molecule:
136. Total number of stereoisomer
(a) C6Hs -C-OH
rH3 ~r*H
CH-CH
(b) CH3 -CH-C2HS
II
o
CH = CH-CH3
CH/
I
CH3
CH = C = CH-CH3
NH2
(c) C6HS -CH-OH
CH=CHz
I
OH
(a) 23
(c) 2s
o
II
137. CH3 -C-CH2
-CH
l'
=CH-CH-CH3
I
CI
144. Identify R configuration:
COOH
(a) Enantiomers
(b) Diastereomers
(c) Identical
(d) Epimers
147. The absolute configuration of the compound is:
CH3
Br+H
CH3
Br+H
CN
C2HS
(b) CH3+C~CH
(a) 2S,3R
(b) 2S,3S
(c) 2R,3S
(d) 2R,3R
148. Which one of the following is a meso-compound?
CH20H
(e)
COOH
(a) H-f--OH
H-t--OH
H+NH
CH3
(b)
H~OH
HO-t--H
CH20H
CH3
2
COOH
D
(c) HO=+=H
HO
H
CH3
+
COOH
. 149. Which compound is optical active?
H
H
N
(d) H2
OH
I
CH3
(a) CH3-
145. The correct statement about the compoud (A)(B) and
I
C-COOH
I
(b) CH3-
C -COOH
I
H
·H
(C):
COOH
COOC2HS
(A) H-f--Cl
(B) H-f--Cl
H-t--C1
H-f--Cl
COOC2HS
COOH
CH3
CH3
I
(c) CH3-
I
C -COOH
I
(d) CH3-
C -COOH
I
OH
COOH
(C) H-f--Cl
Cl
150. Which of following have asymmetric carbon atom?
C1-t--H
COOC2Hs
Cl
Br
I
I
(a) H-C-C-H
I
I
H
Cl
I
I
(b) H-C-C-Cl
I
I
H
H
H
H
(c) (A) and (C) are enantiomers
H
Cl
H
H
(d) CA) and CB) are enantiomers
I
I
I
I
I
I
(a) (A) and (B) are identical
(b) (A) and (B) are diastereomers
146. The following two compounds are
H+F andF+a
Cl
I
H
(c) H-C-C-H
I
H
I
H
Cd) H-C-C-CH3
Br OH
151. Mesotartaric
acid and
d-tartaric
acid
HOOC-CH-CH-COOH
(Tartaric acid) :
I
OH
156.
OH
H
(b) enantiomers
(c) diastereomers
(d) racemic mixture
H
HO
OH
H-+--OH
H
3c
152.
C02H
C02H
I
(a) Position isomers
r
are
H
C02H
OH
HO
HO-+--H
OH
H
H
H-+--OH
OH
C02H
C02H
CO
(II)
H
OH
C02H
.(III)
]
C02H.
H
C2HS
C02H
HO-+--H
The compound with the above configuration is called:
H-+--OH
HO
H
HO
H
HO
H
HO
H
(a) (2S,3S)-2-chloro-3-hydroxypentane
(b) (2S, 3R)-2-chloro-3-hydroxypentan
(c) (2R,3R)-2-chloro-3-hydroxypentane
C02H
(d) (2R, 3S)-2-chloro-3-hydroxypentane
(IV)
Which of the above formulae represent identical
compounds?
153. The correct decreasing pnonty
of ligands
-N02.,-C
:=N,-NH2
and -CH2NH2
is
absolute configuration of an enantiomer is :
(a) N02 >NH2 >C =N>CH2NH2
(b) N02 >C =N>NH2
>CH2NH2
(a) I and II
(b) I and IV
(c) II and IV
(d) III and IV
157.
C02H
(c)NH2 >NO~ > C =N > CH2NH2
(d) NH2 > N02 > CH2NH2 > C =N
154. The full name of the compound
HOH ·r'H;s,
C02H
C02H
H
OH
H
OH
HO
H
H
OH
HO
H
H
OH
H
OH
H
OH
H
OH
Cl
C2HS
C02H
C02H
(II)
(III)
(a) (2R,3R)-3-chloro-2-pentanol
(b) (2R, 3S)-3-chloro-2-pentanol
(c) (2S, 3R)-3-chloro-2-pentanol
(d) (2S, 3S)-3-chloro-2-pentanol
155. How many stereoisomers can exist for the following
acid
H-C(OH) ·C02H
C02H
HO
H
H
OH
HO
H
HO
H
HO
H
HO
H
I
H-C·C02H
C02H
C02H
C02H
(IV)
(V)
Which of the above compounds are enantiomers ?
I
H-C(OH)·C02H
Ca) two
(b) four
(c) eight
(d) sixteen
(a) II and III
(b) III and IV
(c) III and V
Cd) I and V
158. Applying the sequence rule, which of the following
priority arrangements is correct in determining the
R/S configuration of :
(a) -C 6H 5 > -CH
= CH 2 > -CHO > -COOH
(b) -COOH>
=CH2
-CH
-C6H
>-CH
5 > -CHO
164. Which of the following
stereoisomerism ?
(b) 3-methylbutyne-1
(c) 3-methylbutanoic acid
(d) 2-methylbutanoic acid
165. The correct statements(s) about the compound
*
(a) enantiomers
(b) identical
(c) optically inactive
(d) diastereomers
will no
show
I
=C
COOH
=CH-CH-CH3
I
Br
I
OH
OH
is (are):
(a) The total number of stereo isomers possible for X
is 16
.
(b) The total number of diastereomers possible for X
is 50
(c) If the stereochemistry about the double bond in X
is trans, the number of enantiomers possible for X
is 14
(d) If the stereochemistry about the double bond in X
is cis, the number of enantiomers possible for X is
20.
optical
(a) CI-CH=C=C=CH-CI
(b) CI-CH
*
*
CH3 -CH-CH-CH
Br
following
=C =C =CH-CI
(c) H+OH
H+OH
.-
,
Tautomerlsmand Applications of
COOH
. Tautomerism
H
CI
H
Me
CI
9=0
Cd)
166'~
Me
o
161. Which of the following compounds is optically active?
(A)
°
(B)
(a) 1-Bromobutane
Enol content of (A) and (B) is:
(b) 2-Bromobutane
(a) B>A
(c) A = B
(c) 1-Bromo-2-methylpropane
(d) 2-Bromo- 2-methylpropane
HSC2"-..
162. The
exhibits
compounds
(a) 2-methylbutene-1
= CH 2
> -CH
:t::~t:
I
(d) 4
=CH2
159. The two compounds given below are
D
CI
160. Which of the
isomerism?
(c) 3
> -CHO > -C6HS
(c) -COOH>-CHO-C6Hs
(d) -COOH>
(a) 1
/H
/C=C",.{H·
shows:
HSC2
I---COOH
C2HS
(a) geometrical isomerism
(b) optical isomerism
(c) geometrical and optical isomerism
(b) A>B
«n A»> B
167. Which of the following compound will not show
tautomerism ?
OH
0
6
(C)D°
Cb)
(a)
Cd)
(d) tautomerism
163~How many optically active stereoisomers are possible
for butane-z, 3-diol ?
168. Which of the
tautomerism ?
following
D°
D
compound
will
show
o
0
II
o
(a)
(b)
>tJ<
0
o
II
@rC-H
(c)
(a) a> b > c
(b)
(c) b » c> a
(d) a> b > C
~ ~
o172.~
o
(d) ~CH3
o.J:::)=o
(a)
o
(c)
o
II
II
~(ii)
Stability order of enol forms is:
(a) i > ii > iii
(b) ii > i > Hi
(c) iii > i > ii
(d) i > iii > ii
(b) Ph~
o
(d)M
0
(c) Ph~Ph
-C-CH3
174. Which of the following are enol forms of 2-butanone ?
o
"
CH3CCH2CH3
6
(B) Tautomer (B) is:
N
(a) CH3C = CHCH3 and CH3CHCH = CH2
I
0
OH
I
H
I
OH
(b) CH3CHCH = CH2 and CH2 = CCH2CH3
(A)
OH
(a)
'("'
~(iii)
o
170.
./
(a)~
°t{
(d) CH3 -C-CH2
oJlJl
~(i)
173. Which of the following compound has highest enol
content?
o 0
o 0
0
L=(o
(b)
b >a >c
0
~
169. Which of the following compound has negligible enol
content?
-C-O-Et
(c)
o
o
II
CH3 -C-CH2
OH
@
(b)
N
6
I
I
OH
OH
(c) CH3C = CHCH3 and CH2 = CCH2CH3
I
I
OH
OH
N
I
H
~OH
(c)
l.'-!)
(d)
N
(d) None
@
175. Which of the following compounds forms the most
stable enol tautomer ?
N
I
171. Order of stability of enol forms of the following keto
forms is:
o
II
CH3 -C"':""-CH3
(a)
o
o
II
CH -C-CH2
"
-C-CH3
3
(b)
(b) CH3CCH3
(a) CH3CH
OH
0
"
0
"
(c) CH3CCH2CCH3
(d) CH3C-CCH3
II
II
0
0
" 0"
0
0
176. Which of the following
4-phenyl-2-butanone?
is the
enol
form
of
178. Which of the following' will not form an enolate?
V
~
(a)~
(b)
(a)~
o
.~
(C)~
V
(d)
(C)~
177. When compared to the keto form, the enol form of
which of the following compounds is most stable ?
o
0
(i)
6
CH3~
(ii)
(iii)
(iV)Q
6
(a) i
U
(b) ii
Cc) iii
(a) 1
(b) 2
(c)
3
(d) 4
180. Keto and enol forms of a compound are related to each
0
0
179. How many tautomers can you draw for the following
diketone?
.other as:
(a) resonance structures
0
(b) conformations
Cd) iv
Cc) configurational isomers
Cd) constitutional isomers
1.
2.
11.
12.
17.
21.
Cd)
22.
27.
28.
31.
(b)
32.
37.
38.
41.
(c)
42.
47.
51.
(€I)
52.
55.
61.
(e)
62.
65.
66.
71.
(a)
72.
75.
81.
(e)
82.
(b)
48.
57.
58.
Cd)
67.
68.
76.
(c)
77.
78.
85.
86.
. (b)
87.
$)
•(c)
79.
80.
I(d)
89.
90.
~(d) 99.
tOO.
93.
(b)
94.
95.
96.
102.
103.
(a)
104.
105.
106.
111.
112
113.
Cc)
114.
115.
116.
119.
121.
122.
123.
(b)
,
124.
125.
126.
129.
131.
132.
133.
(c) 134.
135.
136.
139.
141.
142.
143.
(b)
144.
145.
146.
149.
91.
101.
(a)
(b)
92.
151.
(d
152.
153.
(a)
154.
155.
156.
159.
(a)
161.
(b)
162.
163.
M
164.
165.
166.
169.
(a)
171.
(c) 172.
173.
(c) 174.
175.
176.
179.
Cc)
(a)
(c~
Level 2 : tical
Problems
1. Which of the following compound will show G.!. ?
Ph"",
(a)
/C=C
HID
A
o
18
(b) H "'C = C / OH
/"'OH
(d) None of these
6. Calculate the total number of stereo isomers in the
given compound ?
CH3 -CH =CH"':""CH =CH-CH-CH-CH-CH3
I
.16
(d) All of these
(c) ~
I
CI
Br
(a) 5
(b) 16
(c) 32
(d) 8
I
OH
7. Which of the following having [E] configuration?
2. Which of the following compound will be pair of G.1. ?
Et -,
/ F
ci ,
/ Et
(a)
"c =C
and
"c =C
,
Cl /.
'" Et
Et /
'" F
.
cr •
/
C=CH
'\C =C/
CH3
OHC/
-, I
C-CH3
I
/ Br
Cb)
"c =C
and
"c =C Br /
'" Br
Cl /
'" CI
(c)
Cl
HO
(a)
Br -,
. CH3
Et -,
/ Et
H -,
/ Et
"c =C <, H and Et / "c =C -, H
H/
F
(b)
(d) All of these
I
sr ,
/ C-C-C
CI/
'" C-C-C
"c =C
I
3. Which of the following will show G.!. ?
Br
(a) CH3 "'C=C=C/CH3
H /
'" H
Cl",
/ Cl
(b) Br /C =C =C\-. Br
. /1
"c =C =C
'" Cl
F
Et",
/ Et
Cd) H /C =C =C =C'" H
H2C '"
(c)
I"
ci >'
I
4. What is the relationship between given compound A
andB?
H"
/COOH
HOOC '" _ / COOH
"C=C
H/C-C",
H
HOOC/
'" H
(Maleic acid)
(A)
(B)
(b) Geometrical isomers
(c) Conformers
(d) Structural isomers
5. Which of the following having highest B.P.?
CH"
/ CH
3 "c =C
3
H/
"'H
C =C/
CH2/
OCH3
"'C=N
I
Br
8. Which of the following will show G.I. ?
OOH
(Fumaric acid)
(a) Optical isomers
(a)
(d)
(a)
(e)
G
Q
(b)
(d) All DE these
D D
9. I-bromo propene will show?
(b)
H "'C =C/
CH3
H3C/
"'H
Cc) Both (a) and (b)
(a) Geometrical isomerism
(b) Optical isomerism
G
OOH
( 56 '
(c) Structural isomerism
(a) Enantiomers
(b) Diastereomers
(d) Position isomers
(c) Identical
(d) Epimers
15. Which of the following compound will show optical
isomerism?
10. Which of the following 'is trans isomers?
Ca)
0
. (b)
Ph"
(a) H)C
/ Ph
=C =C"'- H
H
I
(b) HO-C-Br
I
Cd)
NH2
Et
11. In which of the following
configuration will given?
(a) D "'-C=C/
H/
compound
syn anti
(c)
H+OH
H
D
"'-H
OH
Et
Cd) All of these
16. Which of the following compound will be meso
compound?
COOH
Et
(c) @-CH=N-OH
(d)
H+H
6>
H
'C=N
H/
(a) H
'OH
H+OH
(b) H
H
Et
H
H
12. Calculate the total no. of geometrical isomers?
e-:
9"
e-:
e-:
9"
(a)
32
(b) 16
(c)
5
(d) 8
CHO
H+OH
(c) H
OH
13. Relation between given compound?
SH
Br
HO+B' HO+SH
CN
CN
(A)
(B)
17. Which of the following compound having maximum
chiral centre?
CHO
(b) Homomers
H
OH
(c) Enantiomers
(d) Not isomers
HO
H
(a)
HfSH
Br
H
C2HS
HfSH
H
C2HS
Br
Me
CH3
CHO
Ca) Diastereomers
14.
HfMe
Cd) H
H-If--OH
Cb)
H
OH
57
NH
COOH
(c)
(c) H+OH
V
L~
(d) All of these
(d)
HToH
COOH
OH
H
18. Relationship between given compound:
CHO
CHO
H--If--OH
HO--lf--H
22. Which of the following will show optical isomerism?
H
Br
'H
I
e» C(C~~ CH3
(ale)
Me
HO
H
H
OH
H
OH
HO
H
H
OH
HO
H
BY,0H
Cl
I
/c.~
(d) F
l Et
U
(c)
CH3
CH2-OH
(B)
(a) Diastereomers
(b) Enantiomers
(c) Identical
(d) Not isomers
19. Relationship between given compound:
23. Which of the following compound will be chiral
molecule?
(a)~
~
'Br
H+OH
HO+H
HToH
HOTH
I
(b) :)C=C=C(:
H
CH3
(A)
I
CH3
CB)
Cc) H3C/
Cb)
(c) Identical
(d) Not isomers
20. Which of the following will be optically active?
COOH
SH
Diastereomers
Ca) Enantiorners
C
~OH
(d) All of these
24. Which of the following compound
centre?
OH
having chiral
OH
(al ~COOH
Me
(bl ~OH
(a)
Br
c\
(b)
H
NH2
Br
21. Which of the following will be optically inactive?
COOH COOH
(al~Cl
(bl
V
Cd)
(c)
Cl
F
.1)
25. How many optically active compound will possible in
the given compound?
CH3 -CH-CH-CH-CH3
I
I
. Br
I
CI
(b) 8
4
(d) 2
4
(c) 2
Cc) Diastereomers
Cd) Not isomers
31. Which of the following will show GI ?
(a)
26. How many optical isomers are possible in the given
compound?
CH 3 -CHCH- CH 3
(a)
Cb) Racemic mixture
I
(a) 3
(c)
(a) Enantiomers
I
I.
I
I
Cb)
(c)
(b) 3
0
0-0-0
Cd) All of these
(d) 1
32. IUPAC name for the given compound is:
Cl
27. Which of the following will be optically active?
A;0H
~B'
(a) V~OH
I
F\;0H
(c) ~.~r
yr
U'~C H
2
U
(b)
5
benzene
(b) 2-Bromo-1-chloro-3-fluoro-5-iodo
berizene
(c) 2-Bromo-3-chloro-1-fluoro-5-iodo
benzene
33. Number of total isomers possible with the molecular
formula C sH 10 :
C
(a)
(a) 1-Bromo-2-chloro-4-iodo-6-fluoro
(d) 1-Bromo-6-chloro-2-fluoro-4-iodo benzene
28. Which of the following will be optically active?
r-\;Et
F
(a)
(c)
10
13
(b) 8
«n 14
34. How many monochloroderivatives
will form by monoehlorination
H3~C~
(e)
Br
~
NH
(d)
~~2
including sterect
?
2
H
(a)
4
(b) 5
7
«n
(c) 6
35. Which statement is wrong?
29. Relationship between given compound?
COOEt
COOH
HO~H
H-li-0H
HO~H
(a)
H-li-0H
CHO
COOEt
(A)
(B)
(a) Enantiomer
(b) Diastereomers
(c) Identical
(d) Not isomers
30. W50% D serine and 50% L serine form a mixture
known as a:
99
are G.L
CH3
CI
Cb) , .,,,~H
~and
«t
17
""JI/
CI
are P.1.
C-OH
are P.L
H
o
(c) HO-C
II
and
II
o
COOH
59
Me
Me
«n H~±~H
(a)
and ~±~~
H==F=OH
Me
are diastereomers
H==F=OH
Me
(a) E
(c) S
gi"
b'''''''111111 His:
~Cl
Br
(b) R
(d) Z
ci.;
(b)
H323
c/o
cr.;
CHi
H,
(c)
CHi
H,
(d)
,./Br
C=C
c=c
c=c
C=C
CHi
'CH
H
(a) (S)-2-bromo-CZ)-hex-3~
en-4-one
37. Which of the following represent E-configuration ?
(a)
(b) R,R
(d) R,S
42. The IUPAC name (including the stereochemical
rotation for the chiral carbon) of
Br
36. The configuration of the compound
.
H3C/
S,R
(c) S,S
(b) (R)-2-bromo-(E)-hex-3en-4-one
(c) CR)- 5 - bromo - (Z) - hex - 3 --'en-2-one
Cd) CS)-5-bromo-(E)-hex~3en-2-one
43. Which of the following compound is achiral ?
CH
/C2Hs
'CHO
/CH=CH2
'Cl
(a)
".(
~'"
o
'1
Cb)
O~
OJ
,(
~\\"" 0
/CH2Cl
(j
'CHC12
(el••
3S. Compound A below
CH2
B-+-=OH
H-t-CI
is:
CH3
(a) is called thero isomer
44.
and
H~H
CHMcH
(b) is called erythro isomer
H3C~H
H
3
3
(c) is called diastereomer
(a) Conformational isomers
Cd) is a racemic mixture
(b) Position isomers
drsr
39. Number of chiral centre in the given compound is:
(c) Chain isomers
45. Geometrical isomerism is not observed in :
Ca)O
(b) 3
(d) 5
(c) 4
40. Total number of conformers of ethane is :
I
(a) 2
(c) 4
Cb) 3
(d) Infinite
41. Assign the configuration of C- 2 and C- 4 of
following molecule :
~H
OHC
1
NH
(elL
Me
Cd) ~CH=CH-<1I
3
CH3
(d) Identical
CH3
Ca) 2
are.
H~H
CHO
5
60
46. Which of the following is correctly match ?
(a) ~NH2
and ~NH/
~
~
(b) ~ ~CI and ~
51. Correct relationship between given compound is:
CI
(Diastereomer)
OH
(c) ~OH
(d)
~T
(Homologue)
and ~
(Not homologue)
OH
I
r~u
and ~
(Chain Isomer)
~
OH
47. What is correct relationship
compound- A & B ?
between
(b) Chain Isomer
(c) Diastereomer
(d) All of these
52. Total number of structural ether possible for given
skeletal formula
H7C3 -O-C3H7
following
i-. HW
s
CI
CI
(B)
(A)
(a) Positional isomer
(a) Enantiomer
(b) Diastereomer
(c) Chain isomer
(d) . Positional isomer
48. Which of following is correct?
(a) neobutyl bromide-S primary carbon
(b) isopentyl alcohol-S primary carbon
(c) isobutyl aldehyde-I secondary hydrogen
(a) 1
(c) 3
53. Correct IUPAC name of given compound is:
~
(a) 2-ethyl-6-methy1cyclohexa-1,2-dienecarboxylic
acid
(b) 3-ethyl-1-methy1cyclohexa-1,3-diene-2carboxylic acid
(c) 6-ethyl-2-methylcyclohexa-l,
5-diene carboxylic
acid
(d) 2-ethyl-6-methylcyclohexa-2, 5-diene carboxylic
acid
54. Total number of structure isomers possible for
C4HgCl2 :
(a)
(c)
(d) Acetonitrile-I primary carbon
49. Choose correct statement:
(a) All organic compound with C = C show
geometrical isomerism
(b) Presence of Multiple bond is only condition for
unsaturation.
(c) Homologue should have different molecular mass
and general formula.
(d) But-z-ene and but-Lene are position isomer
50. Which of following statement is correct, regarding
given molecule?
(b) 2
(d) 4
6
9
(b) 8
(d) 10
55. Which is most stable form among following for given
structure?
(aJ~
(bJ~
(CJ~
(dJr
CI
(a) Locant position of -OH is 3
(b) It is secondary alcohol
(c) It have only one secondary carbon
(d) Degree of unsaturation is 2
56. Which of following compound will show geometrical
isomerism?
61 1
(a)9
(c)
(b)
>=()==C
(d)
U
O~~l
-;=Q-
57. Number of carbons in parent chain of the following
compound are :
1 ·9H ~
~OH
(a) 4
(c) 6
(b) 5
Cd) 7
C
I
H
(a) 4-formyl-6-methyl
cyclo hex-2-ene
methyl
carbonyl chloride
(b) 2- (4' -formyl-6' -methylcyclohex -2'-enyl) ethanoyl
chloride
(c) 4-(3'-chloro-2' oxopropyl-S methylcyc1ohex-2enecarbaldehyde)
(d) None of these
63. Increasing order of dipole moment is :
H3C,
58. What will be configuration of multiple bond of parent
chain?
H./
C=C
./CH3
H3C,
'H
H./
./H
C=C.
(i)
H3C,
'CI
(ii)
./H
C=C
H./
'C2Hs
Ciii)
(a)
(b) E and cis
Ca) E'and Z
Cd) Z
Cc) E
59. Number of possible structural isomers of CsH 10 which
can show geometrical isomerism:
(a) 2
(b) 4
(c) 3
Cd) 1
60. Among following, which has least molecular mass and
can not show only geometrical stereoisomerism :
ii
c-
iii
io
(b)
(c) i» ii> iii
iio
iiic-
i
(d) iii> ii> i
64. The most stable conformer of 1, 2-diphenyl ethane is:
(a) H
~6H5
(b) C6H5~H
H~CJ'5
.
C6H~H
H
(a) D~CH ./
3
(d)Hh
'H
H
(b) D~H
./
'H
D,
(c)
C=C
H'/·
=
C
H¥H
C6HS
./CH3
'H
'
65. Which of the following is optically inactive?
D,
./D
(d)
C=C = C
H./
'H
61. Total number of possible geometrical
(excluding optical)of following:
(a) H2~>O<><~H2
isomer
.~.
(a) 2
(c) 6
(b) 4
(d) 8
62. Correct IUPAC name of following compound is :
CI~_C
Cc) Br~H~Br
Cd)Br~Br
CI
<Br
( 62
66. Which of the following compound
psuedoasymmetric carbon-atom:
(a) CH3 -CHCH
contain
a
Gi2
I I I
Br Br Br
(b) CH3CH-CH-CH-CH3
I
I
I
Br
OH
Br
Cc)
«n All
. (c) CH3 CH-CH-CH-CH3
I
I
I
OH
Br
Br
71. Which is optically active?
Ca) H3C/'f"'CH3
CI
Cd) CH3 CH CH CH-CH3
I I I
Br OH CI
CH
COOH
H-+-OH
F$
67. CI
Sr
CH
3 H
H$
Hand H
H
H
CH3
(a) @-CH
Cb) Enantiomer
(c) Identical
(d) Structural isomer
H
CH3
M M
and
H
CH3
H3C
H
(e)
(b) Enantiomer
Cc) Structural isomer
(d) Identical
69. Which of the following is resolvable?
CH3
I
. ·CI~
both are:
H
= CH-CH3
/CI
(b) CI~C'CI
(a) Diastereomer
(a) CH3-C-H
0
72. Which can show geometrical isomerism?
Sr
CH3
H
«n
Cc) H+OH
COOH
CI
F both are:
(a) Diastereomer
H3C
68.
3
HO H
I
(b) CH3-C-H
I
I
OH
CH3
OH
::0
Cd) All
73. Given molecules are:
CH3 .
CH3
H~OH
HO~H
Cl+H
H3C+H
CH3
CI
(a) Identical
(b) Diastereomers
(c) Enantiomers
(d) Structural isomers
I
(c) C2H3 -C-H
74. ~
I
NH3
Ell
70. Which of the following has plane of symmetry ?
H3C,/CH3
(a)
C= C=C
H/
~~---~~-.
'H
and~lare:
. (a) Positional isomer
(b) Chain isomer
(c) Identical
(d) Metamer
75. Which of the following alkenes is not show G.I. ?
(a) H2C =CH2
Cc)
H3C,
H3C/
(b) CH3 -CH
C= CH2
0
•
Cd) All
=CH2
63
76. The possible number of monochloro products in given
reaction is :
(a) 10
77. The compounds
.
.
ISOmerISmare :
which cannot
(a)-O
(e)
(b)
--y
show geometrical
-Q-
(c)
CH2 =CH-CH2
and ~are
I
are
geometrical
and CH3CH2CH2NH2
(a) chain isomerism
(b) position isomerism
(c) functional isomerism
(d) all of the above
(a) methanol
(b) acetone
(c) diethyl ether
(d)
dimethyl ether
(a) 1, 2, 2
(b) 1, 2, 1
(c) 2, 1, 1
Cd) 3, 0, 1
(i)
(r
CI
and
((Cl
I
::::....
Cl
OH
H
Cti)~
~OH
isomers
(d) ~
(CH3hN
86. Examine the relation between the following pairs of
compounds:
Cl
OH
U
(d) Metamers
85. The number of primary, secondary and tertiary
amines possible with the molecular formula C3H9N
respectively :
are metamers
and
Cc) Functional isomers
84. An isomer of ethanol is :
78. Select the correct statementts) :
Me,
/OPh
Me........
/H
(a)
C=C
and
C=C
H/
<, H
H/
<, OPh
(b) CH3 -C-CH3
tautomers
(b) Position isomers
and ~
and
OHtr°
::::....
I· .
are positional
79. The total number of structural isomers of C4HUN
would be:
(a) 4·
(c) 5
(a) All (i), (ii), (iii) are identical
(b) 7
(d) 10
(b) All (i), (ii), (Hi) are isomers
80. Which of the following pair is the chain isomer?
(a)~,~
(b)
Cd)
0,0
>-<,
>y
81. How many geminal dichloride with different formula
are possible forC3H6C12 ?
(a) only one
(b) two
Cc) three
Cd) four
and
represent:
(d) NH=<>=N-H
o
II
(a) Chain isomers
83. The compounds
(b) 11
(d) 8
Cc) 12
82. What is the relation between 3-ethylpentane
3-methylhexane ?
(c) (i), (ii) are identical, (iii) is isomers
(d) (i) is identical and (H), (Hi) are isomers
87. Given compound shows which type of isomerism?
o
0
@-~-O-O
and O-~-o-@
o
(a) Chain isomerism
(b) Positional isomerism
(c) Metamerism
(d) Functional group isomerism
0
t 64
(a) Chain isomers
(b) Position isomers
(c) Functional isomers
(d) Identical
92. Which one of the compound is not isomer of others?
Functional isomers
~e~
Ca)
~t
CgJ Et and C9l.Me
Metamers
(c)
0'
Cb)
(I)
Cd)
93. CH3-CH2-NH-CHO;
Metamers
Me....--N-Me
@
CQJ .
Functional isomers
(a) TFTF
(b) FTTF
(c) TTFT
Cd) TTFF
(a)~
Cb)~
(Cl~
(d)~
90. Which' of the following is not the correct relationship?
Me
I
NH2
CO
(ii)
Which type of isomerism is observed between Ci)and
(a) Chain isomers
(b) Position isomers
(c) Functional isomers
(d) Metamers
(i)~o~o~
(a) chain isomers
(b) positional isomer
(c) metamer
(d) functional isomer
95. Which of the following is a pair of metamers ?
y'
MeliMe
(ii)
CH3-CH-CHO
94. The correct relationship among the following pairs of
given compounds is :
o
0.·
89. Which compound is not the isomers of 3-ethyl.2methylpentane ?
(i) Me*Me
<Cc>
(ii) ?
~2-NH-CH3
and
<>-<>
(a)~,~
OH
O-Me
Me
y,
Me
(b)OA
(iv)A
(ili)~
d
V'
YO-Me
(a) (ii) and (iv) are metamers
.
OH
(b) (i) and (ii) are functional isomers
(c) (i)and
(iii) are chain isomers
(d) (i) and (iv) are positional isomers
91. What is the correct relationship between the following
compounds?
CH3 -CH2-CH-CH2
-CH3,
I
.
CH3
CH3 -CH2
o~
I
96. Geometrical isomers differ in :
(a) position of functional group
-CH2
-CH2
-CH2
(b) spatial arrangement of atoms
I
(c) position of atoms
CH3
Cd), length of carbon chain
Isomerism
97. Stereoisomers have different :
103. The" E"-isomer is :
(a) Molecular formula
(b) Structural formula
(c) Configuration
(d)
Molecular mass
98. Which of the following compounds has restricted
rotation?
H3C.,-...
/CH3
a)
C=C
(
H3C/
<,CH3
F......... /H
(a)
Cl/
C=C
<, Br
(b)
H3C......... /CH3
H/C=C
H
(c)
H3C......... /C2Hs
C=C
H/
<, CH(CH3)2
(d) none of the above
104. The "Z"-isomer is :
Cl.......... /H
(a)
C=C
(c) @-C=C-@
F/
(d)
99. Which of the following compounds does not have
restricted rotation ?
CH3
(a)
O-
CH3
Br.........
(c)
<,Br
Allofthese
ci-"
C=C
(b)
0
r r
H
/CH3
H
3
«n H-C-C-H
<, H
I
Br
(b)
I
Br
100. Which compound can show geometrical isomerism?
/CH3
F/
<, C H
C-C
2
s
CH3......... /Cl
C=C
()
c C2HS/
<,COOH
(d)
3
ci.,
HOOC.......... /COOH
C=C
H/
<, H
105. Which of the following compounds cannot show
geometrical isomerism ?
(a) CH3CH=C(CH3)2
(b) CH3CH=CH2
(a) Cl~Br
(c) CH3CH=CHCH3
Cl
(d) CCH3)2C=CCCH3)2
isomerism?
A
CH3
101. Which of the following will not show cis-trans
H3C"r-{CH3
Cc))--\.
(d)
H3C
CH3
H3C
CH3
106. The total number of geometrical isomers possible in
following compound is :
(b) CH3 -
CH-CH
= CH-CH2
-CH3
Ph-HC=HC-Q-CH=CH-CH3
I
CH3
(c) CH3 -CH
=CH-CH3
(d) CH3 -CH2
-CH
(a) 2
(c) 6
=CH~CH2
107. The total number of geometrical isomers possible in
-CH3
102. Geometrical isomerism is shown by:
H.........
/1
H.........
/1
(a) /C=C.........
Cb) CH /C=C <, B
H
fu
r
3
H.........
(d)
CH /
3
/Cl
C=C
(b) 1
(d) 8
<, Cl
following compound is :
[:>-CH=CH-CH=CH
(a)
4
(c) 3
(b) 6
(d) 2
-<1
108. The number of geometrical isomers in the following
compound is :
CH3 -CH =CH-CH
=CH-C2HS
n» 3
(a) 4
(c) 2
Cd) 5
109. Number of chiral carbon atoms in the compound X ,Y
and Z respectively would be :
Me
Me
MevMe
6
6
X
(a) 0,2, 1
(b) 1,0, 1
(c) 1,2, 1
Cd) 1,2,
115. The correct configuration assigned for compound (i)
and (ii) respectively is :
CH3
COOH
I
(i)H+CH3
(ii) HOOC'!~COOCH3
COOCH3
(a) R,R
H.
(b) S,S
(c) S,R
(d) R,S
116. The R/S configurations
respectively:
Z
Y
(a) 0
(c) 3
°
of these compounds
H°)5.~H3HS\JH
lQJ
~COOH~
2
110. Number of chiral carbon present in the following
compound is :
CH3 - CH-CH2 -CHCH-CH3
.
I
I
(a) R,R,R
(b) S,R,R
OH
Br
C2Hs
(c) R,S,S
(d) S,S,S
(a) 2
(c) 4
117. Which of the following compound has plane of
symmetry (POS) but not centre of symmetry (COS) ?
(b) 3
(d) 5
111. Which of the following have asymmetric
atom?
Cl Br
H Cl
I
(a) H-C-C-H
I
I
carbon
(b) H-C-C-Cl
I
I
I
H
H
H
H
I
I
I
I
I
I
I
I
H
H
Br
OH
-CH3
(a) positional isomers
(b) enantiomers
(c) diastereomers
(d) racemic mixture
(a) H+OH
Br
. CH3
(c) Br+oH
following
compound
Hf-d
P---fH
l
has
(c)
Br
112. Meso-tartaric acid and d-tartaric acid are:
113. Which of the
configuration ?
CH3
H
Br
H
Cl
C-C
~H
(b)
I
(d) H-
J---dr
H
I
H
H
(c) H-C-C-H
\jH3CHO
-"'"
I
are
" S"
OH
(b) Br+CH3
H
H
F
118. The two compounds given below are:
D
Cl
H~Br
I~H
CI
I
Br
H-t-
D-t-H
(a) enantiomer
(b) identical
(c) meso compound
(d) diastereomers
119. How many stereoisomers can exist for the following
acid?
H-C(OH)·
CH3
C02H
I
Cd) HO+Br
H
H
114. The number of optically active isomers observed in
2,3-dichlorobutane is :
(d) ~
H-C·C02H
I
H-C(OH)
(a) Two
(c) Eight
·C02H
(b) Four
(d) Sixteen
67
120. CH3 -CH-CH-CH-CH3
126. In which of the following has minimum torsional
strain and minimum van der Waals, strain?
I
I
I
Br
Br
Br
Total number
compound is :
of
stereoisomers
(a) 6
(c) 8
in
the
YKH
above
(ii)H~CH3
(b) 4
(d) 16
CH3
121. Total number of stereo isomers of the compound is
given below
CH3 -CH-CH-CH3
I
I
OH
Br
(a) 2
(c) 6
H~CH3
(iV)H~CH3
CH3
(b) 4
(d) 8
122. How many stereoisomers of the following molecule
are possible?
HOOC ·CH = C = CH ·COOH
(a) i
(c) iii
127. The dihedral angle between two methyl groups in
partially eclipsed conformation n-butane is :
(a) Two optical isomers
(a) 180°
(b) Two geometrical isomers
Cc) 90°
(b) 120°
(d) 109°28'
128. Which of the following is most stable?
(c) Two optical and two geometrical isomers
(d)
(b) ii
Cd) iv
YKH
None
123. Total number of stereoisomer of compound is given
below
CH3 -CH =CH-CH-CH
=CH-CzHs
I
(b)
C
H~CH3
.
CH3
Cl
(a) 2
Cc) 6
(b) 4
8
«n
(d) H~CH3
124. CH3 -CH-CH-CH-CH3
I
I
I
Cl
Br
OH
Total number
compound is :
(a)
H~CH3
CH3
of stereoisomers
6
in
the
(b) 4
(d) 16
(c) 8
(a) 2
(c) 4
H
H~H
H3C~CH3
H
(a) conformational isomers
(b) stereoisomers
(ii)
129. The possible number of alkynes with the formula
CSH6 is :
(a) 2
Cb) 3
(d) 5
(c) 4
130. How many isomers of C sH II OH will be primary
alcohols?
125. The two structures (i) and (ii) represent :
(i)
above
Hh
(b) 3
Cd) 5
131. Number of isomeric forms of C7H9N having benzene
ring will be :
H3C~H
CH3
Ca) 7
(b) 6
(c) 5
(d) 4
132. Which of the following is an isomer of diethyl ether?
(c) constitutional isomers
(a) (CH3)3COH
(d) identical
(c) C3H70H
(b) CH3CHO
(d) (CzHs)zCHOH
133. Total number of isomeric alcohols with the formula
C4HlOO is:
(a) 1
(c) 3
(b) 2
(d) 4
134. The type of isomerism found in urea molecule is :
CH3
I
(iv) C2HS -
CH-C2HS
it is true that :
(a) All four are chiral compounds
(a) chain
(b) position
(b) only (i) and (ii) are chiral compounds
(c) tautomerism
(d) none of these
(c) only (iii) is a chiral compound.
135. The number of geometrical isomers in case of a
compound with the structure
CH3 -CH =CH-CH
=CH-C2Hs
is:
(a) 4
(c) 2
(b) 3
139. Amongst the following compounds, the optically
active alkane having lowest molecular mass is :
(a) CH3 -CH2
(d) 5
136. Which one of the following will show geometrical
isomerism?
CH2CI, /CH3
C
(a)
H/ 'CH=C(CH3h
CH3,
(b)
(d) only (ii) and (iv) are chiral compounds
/H
.
C
CH2CI/
'CH=C(CH3h
CH2=CH,
(c)
C
H/
/CH2CI
'CH=CH2
(d) CH3CH2CH=CHCH2CH3
137. Which of the following does not show geometrical
isomerism?
-CH2 -CH3
CH3
I
(b) CH3 -CH2-CH-CH3
H
-{-<1
(c) CH3
C2HS
(d) CH3 -CH2 -C
=CH
140. Which of the following compounds is not chiral ?
(a) 1-chloropentane
(b) 2-chloropentane
(c) 1-chloro-2-methylpentane
Cd) 3-chloro-2-methylpentane
H02C
141. The absolute configuration of
(a) 1, 2-dichloro-l-pentene
(b) 1,3-dichloro-2-pentene
(a) R,R
(c) 1,1-dichloro-1-pentene
Cc) S,R
(d) 1,4-dichloro-2-pentene
138. Among the following four structures (i) to (iv)
CH3
I
(i) C2HS- CH--C3Hy
°
1/
(ii) CH3 -C
H
(iii) H_CEfl
I
I
H
CH3
I
- CH-C2HS
C02H
Ir--i"UIlIiOH
HO H
R,S
(d) S,S
is:
H
(b)
142. The alkene that exhibits geometrical isomerism is:
(a) 2-methyl propene
(b) 2-butene
Cc) 2-methyl-2-butene
Cd) propene
143. Out of the following, the alkene that exhibits optical
isomerism is :
(a) 3-methyl-2-pentene
(b) 4-methyl-1-pentene
(c) 3-methyl-1-pentene
Cd) 2-methyl-2-pentene
144.
Structure
S.No.
1.
A
3.
~
5.
",
-
G.I.
"
s.xe.],
9.
11.
13.
15.
17.
~
4.
~
6.
A
L
6H
A.
n
't:(
0
~
8.
~
10.
~
12.
A
14.
K
16.
c(
18.
20.
22.
21.
~
23.
:t=(
G.I.
"-
~
19.
Structure
2.'
~
7.
,,'
O!, "1!
!'
24.
n;
:t=t
.~
.
'
Obi~ctive CMm;,stD!, lor~EETIAIlMS·
.~
s.xe.!
25.
, . 'l~;1,
Structure
)=(
4
"c'k,
,~:
..
'
.~. .,
'G.I.
"
~,
.,j
S.No;
Structure·
£
,
+:
G.I.
26.
~
27.
28.
>c(
~
29.
Cll=:{.
:ex:
31.
Br
33.
tr:
B
30.
Br
'
32.
Cll=(
34.
Cl>cJ
Br
Cl~
F
35.
37.
c(
HOD
36.
38.
39.
40.
.~
41.
)=(0
HO~
)=(
S::c
42.
~F
43.
b=(
44.
)-=(
45.
~
46.
~
48.
if
50.
if
47.
iY
erN
/OH
49.
'.
. ,tt ..'
~
j
",,",
S.No,.
51.
c..
..Structure
Iil, ';:"
.(y6
, ~'
'"
v
,,),
,'
I\,G.I.<. ' >ii
.
S.No.
52.
=
c;
/OH
N
NH
53.
6
54.
6
¢
/OH
N
/OH
N
55.
,
D
56.
57.
U
58.
Q
59.
H~.JJH
60.
HNj
LNH
<,
61.
N-N
63.
T
65.
67.
<,
/
62.
LJ
:cr
T
HN/'..NH
\:=l
C('OH
N,
LN <,
64.
HN~H
66.
6
68.
0)
LJ
69.
HN=NH
70.
0=0
71.
-,N=N
72.
25
73.
8
-,
74.
.
t ':;'"
fj' ;';. StrUcture
'"""
I ~"'"
D
,
'1
e.
;.:""
G.I.·
,
,-
r 72 J
• 1I'i
S.No.
'
Sttue~re
I,
"j
..<\'
-',JJl'L
,~
j
".
~.I. ",
"
'~
S.~O.
""
'
"iI
"
~tructure
/OH
75.
76.
H~
~N
NH
/
HO
/
77.
78.
N~N
-r-,
/
79.
81.
83.
85.
==<
~
80.
"=<
82.
<.
84.
~
>=<
86.
88.
87.
-:
~
"=C
~
.,
90.
89.
~
91.
>=r
\
92.
,
,
-
.
-
-
~
X
»<: ./
1'1",
;;
(T.I.
.
:~'
'c
,,,
" <.. ,:
structure.
S.No.
,}
105.
51.1•
. , S.No.
;i(>ti.. i.
,
>
~tt:!:tcture~,~'
106.
~
107.
/""
~
'r>:
108.
109.
110.
~
111.
112.
~
v'<:
~
~
113.
~
145.
N02 COOH
Cl
N02 COOH
2.
1.
~
COOH
~
N02COOH
N02
H
3.
H,
/C=C=C,
CH3
..."H
CH3
4.
D+CH3
CH3
",COOH
Ph
5.
HOOC~COOH
§§'
"~H
C
6.
I
CH3
Cl
7.
H3C+H
8.
H~H
Br
9.
F~Br
H
R
H
D
10.
~
, ' ,:<\~~<.Y~I:.~
".
:.".
iii
11.
12.
13.
14.
CH3--<)--CH3
,
.u,
Cl
16.
Cl
CH3
Cl
18.
17.
¢
CH3
20.
6'
10.
C3H6C12
146. Calculate the total number of structural isomer.
·11.
CsHlO (only one benzene ring)
.12.
C7HsO (only one benzene ring)
1.
C~-!s
13.
CSH12
2.
C3H6
14.
C7H14 (cyclobutane ring)
3.
C~12 (having cyclobutane ring)
15.
CsHlOO (only aldehyde and ketone)
4.
C~6
16.
CsHlO (cyclic)
5.
C7H16
17.
CsHnBr
6.
C4HlOO
18.
C~l1N
7.
C~14
19.
C3HSBr3
8.
C3H~
20.
C7H7Cl (only one benzene ring)
9.
C~12 (cyclopropane ring only)
21.
CsH120 (only ether)
(cyclic)
Ilso-",'o~i"m
,::'i.,;~.,f~£~;J;i.~~!i,t~-.~
"...',,'':14,',;,,~~m;;/.t,·1,-:~}iE
'}S': '[i*,TI~f_~"',;;;0.I'i)
147. Find the number of stereo center and chiral center in
all structural
isomers of gives molecular
formula:
Stereoc-e
nter
S.No. Molecular Formula
''''1'
CH3
(xi)
CH~
3
/CH3
C"""
H
'
Chiral
Center
J>=
3
(i)
Ce;H12 (open chain)
(ii)
Cc)112 (excluding cyclopropane
ring)
(iii)
Ce;H14
(iv)
C3H6Cl2
(v)
CsH12
(xiv)
(vi)
CsHlO (all cyclic isomers)
(xv)
(vii)
CSHllBr
(xii)
CH
/CH3
C"""
CH3
CH
3
(xiii)
CH3»=
CH3
CH
3
-
/CH3
C"""
CH3
CH3-CH-CH2
"0/
2, 4- Hexadiene
yCHCOHlCH3
(viii) C4H6 (all cyclic isomers)
(ix)
··,g·;iT;:~~.ir~:r,(
75
(xvi)
C7H14 (cyc!opentane ring)
Cl
(x)
148. Find relationship
between
given pairs as enantiomer,
-.-
S.~o. Identify the relation;.,
T
H
1.
~I/I!HT
~"I/fH
Cl
D
Cl
3.
4.
~'If!£tF
~II$I
Cl
D
I
F
2.
~
Br
Cl
Br
T+D H+D
D+: C+F
H
F
F
T
CH=CH2
D
Cl
CH=CH2
;~j
diastereomer
or other:
Bnantiomer
Ditastereomer
"'"
e.
-"F
Ii
, ~".Other
ill,.
-I!!,~ -.
·r 76 1
r!$
';0
... II
S.No.. Identify the relatio.n"
H+-OH
6.
se 1il.l
.'.'"
.~
H+OH
HO-+-H
HO-+-H
Et
7·O::CX::
Me
··9
9
.:Dy
Br
Br
9.
§
T
T
s: Y"
OH
10.
OH
Et
11.
Me
H=+=OH H=+=OH
C}
.
C}
H
Me
Et
H
12.
0
OH
13.
H
~
H
CH3
~H ~~H
,.'
Other
r
77 }
~o~o
(A)
(B)
-v-
14.
~o
(C)
(D)
CH=NH
~CH=NH
~~ 0
---'
15.
o
o
o
(a)
(b)
l-0H A ~
-\ F\
~!·~Me
16.
rOH
H
(a)
18.
H
Br=t=COOH
H=t=Br
H
CN
HO
H
OH
CN
(a)
(b)
Jf Jf
H
..I
Br
Br
(a)
(b)
Me
B'1---{
r
~~..
~~..
~'
19.
Br
..
0
Br
""H
(b)
OH
A A
(a)
(b)
- CH3
CH3
21.
\
H
H
(a)
20.
a
(b)
COOH
17.
~Me
~C\"Ii!tt;(H
H+OH HO+H
H
OH
H
CH3
CH3
(a)
(b)
CH3
OH
H+OH
HO
H
CH3
(c)
.
Obje,ctive Chen,.istr:;>!.{£rNElfT/AIlM§
22.
COzH
H+OH
H-t-0H
COzH
HO+H
H0-tH
COzH
COzH
(b)
(a)
23.
I
24.
I
Br
OH
I
l\
H
l\
HW~
C1 Br
H)/D
OH
Br
H)/I
H~
F
C1 F
HO
OH
CH3
••
25.
-1~••
and Br+H
••••
26.
~Hand
27.
~
CH2CH3
•
~OH
~OH
28.
and
HO
H
~ HO
wH
and
~
H
OH
HCk
~
29.
"..~
HO~\"
CHzOH
~CH20H
and
HCk
~~•.
30.
31.
"..~
HO~'"
CHzOH
Ho:$H
H
and
and
~CH20H
H3C
~
HO
OH
H
~
~•.
HO
*~"
CHzOH
H
CHzOH.
H
~
32.
H"''/5
CH3
CH
3
and
H,o.;.::;
H
~H3
W H
.
79
.
"":
S.Ne.
Itien.ffl' tJte,'!ttati
•.
Op,'i.!~;;~'~~j:~~i'
33.
H
1
,,,~,It'l .'
~: ~:
~: Bf+H
~: ~:
and
H
CH3
CH3
CH3
34.
H
and
H
35.
H
and
Br
CH3
36.
H3C
Br
C02H
CH3
CH3
~OHand
H3C~
OH
37.
(CH3hC
38.
J::::JI
and
(CH3hC
cQ=dctrCH3
cQ H3}b
CH3
39.
and
CH3
40.
41.
H;&
1)
:l) 1)
and
and
i:
,,;:i\l\~0'~F'I'~~Ltiom~
J::::J
'
I
~~=~;"
• ~'~
, l!l$\!l!~e~ther'
'~ ' ..~
~
l~
,QH
f.....H
OHC"
42.
H 11111111"'" C - C
,
and
-,
HO
CH20H
D-erythrose
and
43.
44.
OH
OHC
!?
-,
F~H
HIIIIIII"'''''C-C
HI
"CH20H
D-erythrose
,QH
LH
45.
OHC"
HlllliIlII:;C-C
4
HO
and
"CH20H
D-erythrose
HO H~r H
46.
XX
XX
H OH~r H
and
HO HBr H
47.
,
Br H !jOH
and
HO H~r H
48.
~
~.
H
and
HO HBr H
49.
XX
XX
XX
XX
XX
and
Br!j
OH
H OH!j
Br
50.
tJ
~H3
H,~~Br
51.
I
H'!~CH3
F
and
Br,~~CH3
I
F'!~H
CH3
"',>'
S.No. Id~tify,t,h~
52.
re,l,a~on?
qCl
d~
d)J:CI CILJCI
57.
Cl
Cl
. ".J': '8;,13'"
\"
CH2CH3
HO+H
HO+H
Cl
H
Cl and H
CHzCH3
CH3
CH3
H+OH
HO+H
H
. Cl and Cl
H
CH3
CH3
uandQ
~andU
H
Cl
Cl
Cl
H
Cl
CI
H
.
~H2CH3
CH3CH2••••.. <;:--CH3
~
H
59.
~,,,:
Enan~~mef I"':"f)i~~~«;re~mer
Ill'
Cl
,H2Cl
58.
,>1z~ ,~\(
,
and
CH3
56.
.''>
dl,
Cl
CH3
55.
5' :;
:""
'
and
Cl
54.
,,'
'"
Cl
53.
.
HABr
Br
H
and CH3--~ -~
H
and BrAH
H
60.
Q
61.
H3C"
/H
C=C
H3C/
"Br
Br
OCH2CH3
and
CH3
and
H"
/CH3
C=C
Br/
"CH3
CH2Cl
,l:: '
Other
·"~·~~·".~~l
.
0';
• .
.
.~'.#.
S.Ng. Identify:
the-relatien
"'(it}
'.
. ,"':'
,v
62.
;.j~
,
,H3
~H3
Cl•.•.. C.....•• H
H •.•.. C.....•• CH3
r......•
I
CH ••••.
3
and
I
H
H •.•.. C.....•• Cl
~
CH2CH3
H
-
CH3
CH3
CH3
H#qll/t,
64.
CH3
CH3
H#qullt
H
~~\\
H
Et
Et
COpH
COOH
H=+OH
HO
H·
COOH
and
HO+H
H
OH
c,
COOH
H H
H H
'f Y 'f
and
Et
I
H
Cl
Br+Fand Br+I
&.and
H
/\
H
F
I
71.
CH3
CH3
H+Me
and Me+H
H
Me
Me
Cl
70.
".,
Et
H
69.
CH3
H
CH3
H H
68.
''''
and
Et
67.
CH3
and
0 0
''''
""
H~~"
66.
CH3
.."'\\\~
H
~CH3
.\"~'\
63.
65.
·f
0"""1$$
cY and()
ff and'0""
Et
~
". ',\~.,.
.
f,
~
,
.
;:).
,.~,
. Dlaste1.'eomel'
\~.Enan~ont~r"11\
.",
"
""
i(;;".
",,;,
'.O~her
iz
83
~"
""
,,)~!
~, . "","$"",,,,,
'<""
c,
d ~,;,:
,i'
S.l."la.• Identify tlle T~lafiQJ'
72.
H:$H H:$H
H
CH3
,CH3
.
CH3
H
H$Br Br40H
Br
73.
CH3
Br
H
OH
H
OH
Me
MeH
Me H
Et
Et
OH
Et H
74.
Y
~
Me
Et
OHH
75.
OH
V
~
H
H
76.
H
\/
H
H
Cl
D
I
OH
OH
~
H
H
I
Br
)/
Br
H
OH
H
~
I
H
OHH
F
Br
'f
77.
V Y
V Y
H
~
Br
F
HW
Cl
E
F
r )L-l3
HOOH
78.
H
Brx)):H Hx)):Br
H
79.
CH3
H
CH3
CH3
Br
Br
H
Br
H
CH3
CH3
B~WCI B~~a
Br
80.
CH
3CH3
CH
3CH3
Cl
:J,?t~i~
,'"
>1
.".
!'~;r""'4' ;'t'}" , ',/~~;l~I'~ Fi
E,panti0it!et',>;,
mer :,
0'
,
U!l
~",~J,"!:f
OU1't;,r''I<" :,~
84
.·~:~i:l;
'C
S.No.
tJie relation
Identify
-,,-.:
d~H Hi
0,
Br
81.
H
H
,Br
CH3
CH3
H3l')(\CH
o~
82.
Cl
3
iji>
H
CH3
H3C
'OH
H$H
HdiH
H
83.
H
H
H
CH3
Me
84.
H:o/H H:o/H
H
H
H
CH3
H
CH3
H$CI H:$d
OH
Cl
85.
OH
C
H
H
OH
OH
CH3
OH
I
86.
Hd\CH CH CH
z
z
I
and
C"""'I{'/f//H
/C""'I{/III//CH
CH3CHzCHz
3
Cl
CHzBr
I
CH3
I
and
/C\/II/IICI
87.
/C\/III//CH3
CH3CHz
CH CH
z 3
H
CH3Br
I
/\I{II/I/OH
88.
H
CH3
\H
and
I
/\'I{/II/CH3
HO
CHzBr
CHzBr
3
z EnaritioriJ;er
.~Di~te~eotnera
Other
"
CI
89.
CH3+CHzCH3
CH3
I
HIIIII""" .. C
t···",,\\\\\\H
"Br
Bl'OH
HO,
I
HIlIi"""""C
HO'"
/Br
H\I\I\\I,,""Y
CH3
"Br
CH3
92.
H
,t
I
HIII'IJ"",,·C
HO'"
H3CIIIIJ,,,,,,..
HO'fl"""""Br
"Br
CH3
93.
OH
I
HlflIJ",,,,,,,C
HO'"
BrlflIJ""'''.'~
H3C'fI"""""H
"Br
CH3
94.
~"
HO
95.
CH3
I
HIIIIi""""C
HC
3
Enantiomer
CHzCH3
CH3
91.
>
and H+CI
CH3
HO'"
"",,iii
CH3
H
90.
'f
,
S.No. Identify the relation.
I
C,,"'\I\\\\\\D
Br
Br/
.
"
~
'"
.c-C'::"'OH
CI~\"J
"OH
.
~
HO~'
/CH3
/C-C~/QICI
"CH3
H3C
H
H
96.
~OH
./~
'C-C...-.H
H3C".,.J'H
..C-C"'-'OH
H"
CI?"J
H
CI?"J
"CH3
"CH3
H3C
p q
p
H
97.
H3
Br
Br
H
98.
H3
Br
~,
C
H
,
, :l;)iasteveo.mer.
",,'
Ot4er,
j,
99.
OH
OH
100.
~Br
OH
101.
102.
COOH
H3C+H
NH2
H
1.
4.
11.
14.
21.
Cd)
31.
(d) 32.
34.
41.
(~t,42.
44.
51.
(b)
52.
54.
61.
(b)
62.
71.
Cd) 72.
22.
24. '
63.
64.
Cd} 73.
74.
81.
83.
84.
91.
93.
101.
103.
111.
113.
121.
123.
131.
133.
141.
143.
(C)
104.
(e)
144.
1.
No
11.
21.
31.
Yes
41.
Yes
42.
51.
N'Q
52.
No
61.
Yes
62.
39.
71.
49.
50.
54.
59.
60.
Yes
64.
69;
70.
Yes
74.
79.
80.
A
81.
Yes
91.
82.
84.
89.
92.
94.
99.
101.
Yes
102.
111.
Yes
112.
1.
Yes
2.
'No
11.
No
12.
'No
90.
113.
145.
, 3.
13.
5.
Yes", j 6.
15.
No,"
16.
Yes
7.
yes
17.
20.
Yes
( 88
146.
1.
(5)
2.
5.
11.
(4)
1'2.
15.
21.
(6)
8.
147. Short abbreviations *~ (S.C. = Stereocenter) (C.c. = Chiral center)
(i)~'~'~'~
,~
,~
I
, [S.c. ~ 5; C.c. ~ 1]
[S.c.~ 4; c.c.~
[S.c.=zero;
(iii)~'~'~'~
Cl
(iv)~
~
«1
Cl
~
Cl~Cl
Cl
~-t
(v)~
c.c.=zero]
ts.c., 1; c.c.. 1]
*
Cl
2]
[S.c.=zero;
C.C.=zero]
[S.C.=2; C.C.=2]
fu
(vii)
~Br~~~~1
.
"I
T
Br
Br
fu
I ~
Br
I
Br~
[S.C.=3; C.C.=3]
(viii)
D ~ ~
l [SJ
(crlcS cS 6' ~
. [S.c.= zero; C.c.= zero]
[S.c.= 4; C.C.= 4]
I
't
Br
89
[S.c.= 3; c.c. = 1]
[S.C.=2; c.c.=zero]
[S.C.=2; C.C.=2]
rs.c.. 1; c.c.= 1]
*
[S.c.= 1; C.c.= 1]
'k
[S.c.= 4; c.c.= zero]
,(xv)~
*
. ~CH(OH)CH3
[S.c.= 3; c.c., 3]
(XV1)~
CI
14~.
1.
Enantiomer
2.
Enantiomer
3.
Identical
4.
Identical
5.
Enantiomer
6.
Identical
7.
Diastereomer
8.
Diastereomer
9.
Diastereomers
10.
Enantiomer
11.
Positional isomers
12.
Diastereomers
13.
Diastereomers
14.
A, B, diastereomers; B,C diastereomers, A, D·
15.
Enantiomers; A and C diastereomers
Enantiomer
16.
Identical
17.
Identical
18.
Diastereomer
19.
Diastereomer
20.
Constitutional isomer
21.
Enantiomer (be): Diastereomer
Cab) and (ca)
22.
Identical
23.
Enantiomer
24.
Identical
25.
Enantiomer
26.
Enantiomer
27.
Identical
28.
Diastereomer
29.
Enantiomer
30.
Positional Isomer
31.
Enantiomer
32.
Identical
33.
Diastereomer
34.
Identical
35.
Enantiomer
36.
Diastereomer
37.
Diastereomer
38.
Enantiomer
39.
Identical
40.
Identical
41.
Diastereomer
42.
Diastereomer
43.
Identical
44.
Enantiomer
45.
Diastereomer
46.
Diastereomer
47.
Enantiomer
48.
Identical
49.
Enantiomer
50.
Enantiomers
51.
Identical
52.
Identical
53.
Diastereomers
54.
Constitutional isomers
55.
Enantiomers
56.
Constitutional isomers
57.
Enantiomers
I
{ 90
58.
Identical
59.
Enantiomers
60.
Consitutional isomers
61.
Identical :
62.
Identical
63.
Enantiomers
64.
Different Compound
65.
Identical
66.
Enantiomers
67.
Identical
68.
Enantiomers
69.
Identical
70.
Diastereomers
71.
Diastereomers
72.
Consitutional isomers
73.
Diastereomers
74.
Diastereomers
75.
Identical
76.
Enantiomer
77.
Identical
78.
Identical
79.
Identical
80.
Diastereomer
81.
Enantiomer
82.
Constitutional isomer
83.
Other
84.
Constitutional isomer
85.
Diastereomer
86.
Enantiomer
87.
Enantiomer
88.
Enantiomer
89.
Enantiomer
90.
Enantiomers
91.
Enantiomers
92.
Enantiomers
93.
Identical
94.
Different
95.
Enantiomers
96.
Enantiomers
97.
Identical
98.
Diastereomers
99.
Enantiomers
100.
Identical
101.
Identical
102.
Identical
103.
Identical
104.
Enantiomers
Isomerism
91
1
Level 3 : Com etition Corner
1. When trans -2- Butene is reacted with Br2 then
product is formed:
[AIIMS-2013]
(a) Racemic -2,3 dibromobutane
(b) Meso -2, 3-dibromobutane
(c) d-2, 3- dibromobutane
6. In the following the most stable conformation of
n-butane is:
[AIPMT-2010]
(d) l-2,33-dibromobutane
HH
2. The order of stability of the following tautomeric
copounds is:
[NEET-UG2013]
°I
(I)
i-I,C
H
HW
°II
CH2=C-CH2-C-CH3~
Cc) H
°"
o
di
(a)
HWCH
3
(b)
H
H
H
H
H
(d)
H~
CH3 .
HH
II
CH3-C-CH2-C-CH3~
7. Which of the following compounds will exhibit
cis-trans (geometrical) isomerism? [AIPMT-2009]
(II)
OH
0
I
(a) I-Butanol
(c) 2-Butanol
II
CH3 - C =CH2-C-CH3~
(III)
(b) 2-Butene
(d) 3-Butyne
.8. How many stereoisomer
(a) II> III~ I
(b)
I>II>III
does this molecule have
CH3CH =CHCH2CHBrCH3:
[AIPMT-2008]
(c) III> II> I
(d)
II> I> III
(a) 8
(b) 2
(c) 4
Cd) 6
3. Which of the following acids does not exhibit optical
isomerism:
[AIPMT Pre-2012]
(a) Lactic acid
(b) Tartaric acid
(c) Maleic acid
(d) a-amino acids
4. Find the number of stereo isomers of 1,2-dihydroxy
cyc1opentane:
[AIPMT-2011]
(a) 1
(b) 2
(c) 3
(d) 4
9. CH3 -CHCI-CH2
-CH3 has a chiral centre which
one of the following represents its R configuration:
[AIPMT-2007]
C2HS
C2HS
(al
is most stable:
OH
H~
H
HH
[AIPMT-2010]
OH
o»
3
Cb)
H~OH
HMH
H
HO~
H
HH
Cc)
CiHs
(d)
10. Which of the following is not chiral:
(c) 3-Bromo pentane
(d)
H
OH
H C+Cl
C2HS
(b) 2,3-Dibromo pentane
H*OHH
H
3
H
(a) 2-Butanol
(el
Cl+CH
Cl
5. Which of the following conformers for ethylene glycol
(al
H+CH
H-fCl
(d) 2-Hydroxy propanoic acid
3
H
[AIPMT-2006]
( 92 )
11. Which of the following is optically active:
[AIIMS-2010]
OH
OH
ca)O
a
CH3
(b)
OH
6
Cd)
(,(CH2
(b)
6
(c)
H,+CH,oH
A../
(d)
[AIIMS-2006]
. COzH
C2HS
(b) 25,35
Cd) 2R,3R
Ca) 25,3R
Cc) 2R,35
f'O:
COzH
13. Among the following which one can have a meso
form:
[AIIMS-2006]
(a) CH3CH(OH)CH(Cl)CzHs
(b) CH3CH(OH)CH(OH)CH3
(c) C2HsCH(OH)CH(OH)CH3
(d) HOCHzCH(Cl)CH3 .
14. -Correct configuration of the following is
[AIIMS-2005]
of the following is:
[AIIMS 2013]
H+CI
Cl-f-H
NHz
Cd) H,N
N
Y
CH3
(b) HOH,C+H
H
A../
CHCI
(yCHCI
16. The absolute configuration
12. Amount the following L-serine is:
COOH
(a)
.15. The geometrical isomerism is shown by:
[AIIMS-2004]
CH3
OH
(c)
(c) 2R,3S
17. With respect to the conformers of ethane, which of the
following statements is true?
[NEET 2017]
(a) Bond angle changes but bond length remains
same
(b) Both bond angle and .bond length change
(c) Both bond angles and bond length remains same
(d) Bond angle remains same but bond length
changes
18. How many total number of stereo isomers are possible
in following compound :
[AIIMS2017]
CH3 -CH =CH-CH-CHz
-CH3
I
CH3
(a) 4
(c) 6
(a) 2S,3S
(b) 2
(d) 3
(b) 2S,3R
Solution
Q
16. (b) H+-=-CI
CI+-H
~.
Absolute configuration (25,35)
5 or sinister (left) is used for counterclockwise
configuration R or acutus (right) is used for
clockwise configuration.