Beruflich Dokumente
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1
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
CONCEPTUAL IMPROVEMENT
OF ISOMERISM
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2
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP-1
Time: 20 Minut
es
Q.1 Relationship between molecules:
(a)
&
(b)
&
(c)
&
(d) CH
2
OH & O CH
3
(e)
&
(f)
&
(g)
&
(h)
&
(i)
&
(j) CH
3
CH
2
CH
2
NH
2
&
CH CH N
3 2
CH
3
H
(k) O CH
3
& CH
2
OH
COOH
COOH
OH
OH
N
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3
(l)
OH
CH
3
&
CH OH
2
(m)
& CH
3
C C CH
3
(n) CH
3
CH
2
CH
2
CH
2
NH
2
&
(o)
CH C OH
2
O
&
C O CH
3
O
(p)
(q)
&
&
(r)
&
Q.2 Fill in the blanks:
(a) C O
O
& C O
O
are _ _ _ _ _ _ _
(b) O
& O
(c)
H
CH
3
C = C
H
O
are _ _ _ _ _ _ _
&
H
CH
3
C = C
H
O
are _ _ _ _ _ _ _
(d) CH
3
CH
2
CH
2
N
|
H
CH
3
& CH
3
CH
2
N
|
H
CH
2
CH
3
are _ _ _ _ _ _ _
(e) CH
3
CH
2
CH
2
C N
& CH
3
CH
2
CH
2
N
==
C are _ _ _ _ _ _ _
CH CH N
3
2
CH
3
CH
3
N
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4
(f) CH
2
SH
& S CH
3
are _ _ _ _ _ _ _
(g)
CH CH CH C
3 2 2
H
O
& CH
3
CH
2
O
||
C
CH
3
are _ _ _ _ _ _ _
(h)
CH CH CH C
3 2 2
O
CH
3
& CH
3
CH
2
O
||
C
CH
2
CH
3
are _ _ _ _ _ _ _
Q.3 Column matching
Column I
(A)
N
CH
3
H
& CH
2
NH
2
(P) metamers
(B) H
O
||
C
Column II
OCH
3
& CH
3
O
||
C
OH
(C)
&
(D)
&
PhOCO
H
H
C = C
H
O
(S) identical
H
H
C = C
H
O
N
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5
IIT-JEE Chemistry by N.J. Sir
DPP NO- 2
minutes
Compounds
Relationship
1.
&
2.
O
&
O
3.
&
ORGANIC chemistry
Time: 15
4.
&
5.
Br
Cl
&
Cl
Br
6. CH
2
= CH CH
2
OH & CH
2
= CH OCH
3
7.
O
&
O
8. CH CH CH OH
2 2
O
& CH C OCH
3 3
O
9.
&
10.
&
11.
&
12. CH
3
OCH
3
& CH
3
OCH
2
CH
3
N
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6
Compounds
13.
&
14.
O
&
CHO
15.
OH
SH
&
OH
HS
16.
CH
3
H
H
Et
&
CH
3
H H
Et
17.
OH
&
OH
18. OCH
3
&
Relationship
OCH
3
19.
CH
3
CH CH
2 3
H
H
Br
Cl
&
CH
3
CH CH
2 3
H
H
Br
Cl
20.
CH
3
Me
H
Cl
&
CH
3
Me
H Cl
21.
&
22.
N
H
& N
N
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(D)
(A) 1
(B) 2
(C) 3
(D) 4
OH
H
How mnay types of functional groups are presention given compound.
(A) 6
(B) 5
(C) 4
(D) 7
Q.11 The hybridization of carbon atom in the given compound
(A) sp
2
, sp
(B) sp
3
, sp
2
(C) sp
3
, sp
(D) only sp
2
Q.12 Bond X is made by the overlap of which type of hybridized orbitals?
X
(A) sp and sp
3
(B) sp and sp
2
(C) sp
2
and sp
3
(D) none of these
Q.13 The number of sp
2
sp
2
sigma bonds in the compound given below is:
(A) 1
(B) 3
(C) 4
(D) 5
(B) ester
(C) ether
(D) alcohol
(B) ester
(C) ether
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Q.16 Find out the degree of carbon in the following compounds
(a)
CH CH CH CH
CH CH
3 2 2 2 2 3
CH CH CH CH CH
3 2 3
4-ethyl-3-methyloctane
(b)
CH
3
CH
3 CH
3
1,2,7-trimethylcyclopentadecane
(c)
CH
3
CH
3
CH
3
CH
3
1,1,2,5-tetramethylcyclopentane
(d)
CH
3
Q.17 Calculate DBE value of C
4
H
8
and draw possible structural isomer
Q.18 Calculate C
3
H
6
O, DBE value & draw all possible structural isomer.
Q.19 Calculate DBE value of C
5
H
10
& draw all possible structural isomer.
Q.20 Calculate DBE value of C
4
H
6
and draw all the possible structural isomers.
Q.21 Calculate DBE value of C
2
H
4
O
2
and draw all the possible structural isomers.
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10
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 4
Time: 15
minutes
Q.1 Identify relationship between following molecules.
(a)
(b)
(c)
&
&
&
(d)
&
(e) CH
3
CH
2
CH
2
CN & CH
3
CH CH
3
|
CN
(f)
&
(g)
&
(h) CH
3
CH CH
2
CH
3
& CH
3
CH
2
CH
2
CH
2
OH
|
OH
(i)
NH
2
&
NH
2
(j)
&
(k)
&
Q.2 Calculate I.H.D. in the following molecules:
(a)
(b)
O
CH
3
(c)
CHNH
2
(d)
O
O
Cl
CH
3
(e)
O
OH
O
H N
2
Q.3 Calculate No. of o & t/ bonds in the following molecules:
(a)
(b)
(c)
(d)
CN
O
O = COH
Cl
(e) N C C N
N
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11
O
O
||
||
(f) C H
(g)
|
|
C H
C OH
||
||
O
O
C OH
2
bond in the
following structure?
CH CHCH CH
3 2 3
1 2 3 4
CH
3
(I)
H
CH CH
2 3
H
H
CH
3
H
(II)
CH CH
2 3
H
CH
3
H
CH
3
CH
3
(III)
H
H
H
CH
3
H
CH
3
(IV)
H H
C H
2 5
H
H
H
(V)
H H
H
CH
3 CH
3
H
(A) I
(B) II
(C) III
(D) IV and V
Q.5 Which of the Newman projections shown below represents the most stable conf
ormation about the
C
1
C
2
bond of 1-iodo-2-methyl propane?
(A)
H H
H
I
CH
3
CH
3
(B)
H H
H
I
CH
3
CH
3
(C)
H
H
H
I
CH
3
CH
3
(D)
H
H H
I
CH
3
CH
3
Q.6 Among the butane conformers, which occur at energy minima on a graph of pot
ential energy versus
dihedral angle?
(A) gauche only
(B) eclipsed and totally eclipsed
(C) gauche and anti
(D) eclipsed only
(E) anti only
Q.7 Which of the following best explains the reason for the relative stabilitie
s of the conformers shown?
(I)
H
H H
CH
3
CH
3
H
(II)
H
H H
CH
3
CH
3
H
(A) I has more torsional strain
(C) II has more torsional strain
Q.8 Draw the Newman projection that represents the least stable confor
mation of 3,3-dimethylhexane
viewed along the C3-C4 bond.
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Q.9 Draw the Newman structure for the most stable conformation of 1-b
romopropane considering
rotation about the C
1
C
2
bond.
Q.10 Draw a Newman projection of the most stable conformation of 2-methylpropan
e.
Q.11
(a) Write Newman projections for the gauche and anti conformations of
1,2-dichloroethane
(ClCH
2
CH
2
Cl)
(b) The measured dipole moment of ClCH
2
CH
2
Cl is 1.12 D. Which among the following statements
about 1,2-dichloroethane is/are false?
(1) It may exist entirely in the anti conformation.
(2) It may exist entirely in the gauche conformation.
(3) It may exist as a mixture of anti and gauche conformations.
Q.12
H
H
CH
3
CH
3
H
H
; If front carbon is rotated by 180 the conformation formed is:
(A) gauche
(B) anti
(C) partially eclipsed (D) perfectly eclipsed
Q.13
H
H
CH
3
CH
3
H
H
In the given energy diagram for butane the above conformation is repr
esented at
which point
A
B
C
D
E
angle of rotation
(A) A
(B) B
(C) C
(D) D
H
H
CH
3
CH
3
CH
2
CH
2
O
O
||
C
CH
3
; Most stable form of the compound.
Q.19 Draw most stable conformers of
3 2 2
CH CH NH
|
o
& CH
3
3
CH
|
CH
O H
Q.20 What is the effect on dipole moment of 1,2 dichloroethane when the tempera
ture is increased?
Q.21 Most stable conformer of
2
2
CH COOH
|
CH COOH
(succinic acid)
(a) at very low pH
(b) at very high pH.
Q.22 Draw more stable conformation for the following
(a)CH
3
2
3
CHCH
|
CH
|
o
CH
3
(b) CH
3
3 3
CHCH
| |
CH CH
|
o
CH
3
(c)
(d)
(e) C C CH
3
CH
3
CH
3
H
H
Q.22 Compare Rotational barrier.
(a)
3 2 2 3
CH CH CH CH
|
o
3 2 3
CH CH CH
|
o
3 3
CH CH
|
o
(i)
(ii)
(b)
CH CH
2 2
(iii)
CH CH
2 2
(i)
(ii)
(iii)
(c)
CH CH
2 2
Cl Cl
CH CH
2 2
Br Br
CH CH
2 2
I I
CH CH
2 2
F F
o
(1)
(2)
|
(3)
(d)
(i)
(e)
(ii)
(iii)
|
(4)
(i)
(ii)
CH
CH
3
CH
3
CH CH
2
o |
| o
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 5
Time: 15
minutes
Q.1 For the conformation of lowest energy estimate the atomic angles
in the cation and the neutral
molecule drawn below. Provide one number only for each question.
C O:
:
+
O:
:
(A)
(B) C
(C) C
(D) C
O
O
O
C
C
C
Br
H
(IV)
Br
H
(V)
H
Br
(A) I
(B) II
(C) III
(D) IV
(E) V
Q.5 The K
eq
for the interconversion for the two chair forms of methylcyclohexane at 25C is 1
8. What %
of the chair conformers feature an axial methyl group?
(A) 95
(B) 75
(C) 50
(D) 25
(E) 5
Q.6 Which of the following describes the most stable conformation of
trans-1-tert-butyl-3methylcyclohexane
(A) Both groups are equatorial
(B) Both groups are axial
(C) The tert-butyl group is equitorial and the methyl group is axial
(D) The tert-butyl group is axial and the methyl group is equitorial
(E) None of the above
Q.7 Name the compound shown below.
Cl Cl
(A) trans-1, 2-dichlorocyclohexane
(C) trans-1, 3-dichlorocyclohexane
(E) trans-1, 4-dichlorocyclohexane
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(B) K > 1
(D) No estimate of K can be made
HOCHCHF
2 2
(A)
F
H
OH
H
H
H
(B)
F
H
OH H
H
H
(C)
F
H
OH
H H
H
(D)
H
H
H
H
F
HO
Q.10 Most Stable conformer of
(A)
(B)
(C)
(D)
H
H
H
H
H
H
H
H
H
H H
H
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(D)
Q.13 Draw the Newmann projection formula of the most stable conformati
on of 3-hydroxy propanal
across C
2
and C
3
.
Q.14 (a) Below are six conformations for a specific compound. With re
spect to the biggest groups,
determine which structure are eclipsed, anti, gauche, highest in energy and lowe
st in energy.
(A)
(D)
(B)
(E)
(C)
(F)
H
Pr Me
Me
Et
H Et
H
H
+1 +1 +1 +1 +1
Anti All Gauche All eclipsed Highest in
energy
Lowest in
energy
H
H
H
H
Pr
Pr
Pr
Pr
Pr Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Et
Et
Et
Et
H
H
H
H
(P
r
= propyl)
Q.15 The equilibrium constant for the ring-flip of fluorocyclohexane is
1.5 at 25C. Calculate the
percentage of the axial conformer at the temperature.
Q.16 Following eclipsed form of propane is repeated after rotation of
H
H
H
H
CH
3
H
(A) 45
(B) 90
(C) 120
(D) 180
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 6
Time: 15
minutes
Q.1
Column I
ColumnII
(A)
H
CH
3
CH
3
(P) cis-form
(B)
CH
3
CH
3
(Q) trans-form
(C)
CH
3
CH
3
(R) K
eq
is greater than one or equal to one when compound
undergo flip.
(D)
CH
3
CH
3
(S) K
eq
is less than one when compound undergo flip.
Q.2 Write correct order of stability of different form of following compound X
with suitable reason.
CMe
3
Me
(I)
CMe
3
Me
(II)
CMe
3
Me
(III)
Me C
3
Me
(IV)
Me C
3
Me
Q.3 Identify most stable form of given compound
Et
CH
3
(A)
CH
3
Et
(B)
CH
3
Et
(C)
CH
3
Et
(D)
CH
3
Et
Q.4 Dipole moment of a compound W CH
2
CH
2
W is 1.5 D. If dipole moment of its gauche form is
6.0 D. what will be mol fraction of its anti form.
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Q.5 Compare stability:
(a)
OH
HO
and
OH HO
(b)
OH
HO
and
(c)
and
(d)
and
(e)
(f)
and
and
(g)
and
(h)
and
H
R
Keq
R Keq
H 1
CH
3
18
CH
2
CH
3
23
CH
CH
3
CH
3
38
3800
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 7
minutes
Identify E/Z configuration:Q.1
(1) C = C Me
(2)
C = C
CH Cl
2
CH
3
HOCH
2
N
C
(3)
C
H
Me
CH
3
(4)
C = C
Cl
Br
F
I
(5) C = C
O
O
O
O
(6) C = C
O
O
O
O
HOCH
2
N
C
(7) C = C
CH OCl
2
COCl
HOC
HOH C
2
O
(8)
C = C
CN
CH OH
2
HOCH
2
OHC
(9) C = C
Time: 15
Me
(10) C = C
C
C H
C
CH
CH = CH
2
CH CH
2
CH
3
CH
3
CH
3
CH
3
Me Me
(11)
C = C
C C H
C
N
CH
OH CH
2
Me
Me
(12) C = C
H
D
F
Cl
(13)
C = C
CH C
2
I
CH Cl
2
I CH
2
Cl CH
2
H
H
(14)
C = C
CH CH
2 3
CH CD
3
Cl CH CH
2 2
HO CH CH
2 2
D
(15)
C = C
CH
3
OH
CH CH
3 2
HS
(16)
H
(17)
H H
(18)
Cl
Et Me
Br
(19)
C = C
CH
3
H
CH
3
H
(20)
C = C
CH
3
H
CH
3
H
N
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21
(21)
H H
(22)
H
H
(23)
H
H
(24)
O
O
(25)
(26)
(27)
H
Br
CH CH Cl
2 2
CH CH Br
2 2
(28)
H
Cl
O
O
(29)
H
Br
CH
3
OCH
3
Q.2
1. Which of the following will show G.I. in acidic medium
(A)
O
(B)
O
(C)
O
(D) C = O
H
H
(E)
O
(F) O
2. Which of the following will show G.I.
(A) CH
3
CH
2
O
||
C NH
2
(B) CH
O
||
C NH CH
3
(C)
O
||
C NH CH
3
(D)
CN
Me
Me
O
Cl
Cl
(J)
Cl
Cl
(K)
Cl
Cl
(L)
Cl
Cl
N
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 8
Time: 15
minutes
Calculate of geometrical isomer:
Case I If both the ends are different
2
n
when n is number of stereogenic area or t bond which can show G.I.
Case II If both the ends are same
2
n1
+ 2
p1
If n = even ; P = n/2
If n = odd ; P =
n 1
2
+
Hint Rules for cyclic system:(i) 3 member to 7 member cyclo alkene exist in only cis form.
(ii) 8 to 11 member can form cis & trans but cis is more stable.
(iii) from 12 member trans is more stable.
Q.1 Calculate total number of only geometrical isomers in following compounds (
Theoritical).
(1)
(2)
(3)
(5)
(4)
(6)
(7)
(8)
(9)
(11)
(10)
H
Me Me
H
(12)
H
H
(13)
H
Me Me
H
(14)
H
Me
Me
H
(15)
Me
Me
(16)
(17)
(18)
(19) CH
3
CH=CHCH=CHCH=CHCH
3
(20) CH=CHMe
CH =HC
2
(21) MeCH=C=CHCH
2
CH=C=C=CHMe (22)
N
.
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(23) BrCH=C=C=CHCH=CHBr
(24)
(25)
(26)
H
H
CH
3
CH=C=CH
2
(27) CH
3
CH=CH CH=CHCH
3
(28) CH
3
CH=C=C=CHCH=CHCH
3
(29)
(30)
(31)
H
CH
3
(32) CH
3
CH = CH CH = N OH
(33)
O
O
Q.2
&
are
Q.3
-------------------------
&
are --------------------Q.4 Calculate total no. of geometrical isomers for the following:
(A)
(B) CH
3
CH = CH CH = C= CH CH
3
(C) CH
3
CH = C = C = CH CH
3
(D) CH
3
CH=CHCH=C=CHCH=C=C=CHCH
3
(E)
Q.5 C = N
Et OH
CH
3
Correct name of above compound is
(A) syn methylethyl ketoxime
(B) anti methylethyl ketoxime
(C) syn ethylmethyl ketoxime
(D) syn methylethyl ketoxime
Q.6
C
Cl H
is
(A) E
(B) Z
(C) none
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 9
Time: 15
minutes
Q.1 C = C = C
CH
3
H
CH
3
H
l
1
C = C = C
CH
3
H
CH
3
H
l
1
(I)
(II)
I and II are not geometrical isomers of each other because
(A) I
1
= I
2
(B) I
1
> I
2
(C) I
2
> I
1
(D) they are geometrical isomers
Q.2
C = C = C = C
CH
3
H
CH
3
H
l
1
C = C = C = C
CH
3
H
CH
3
H
l
2
(I)
(II)
I and II are not geometrical isomers of each other because
(A) I
1
= I
2
(B) I
1
> I
2
(C) I
2
> I
1
(D) they are geometrical isomers
Q.3 MeCH = CH CH = C = CH CH = CH
2
Total number of geometrical isomers possible for above compounds are:
(A) 16
(B) 8
(C) 4
(D) 2
Q.4 Find total number of Geometrical isomerism of following compounds.
(A) CH
3
CH = CH CH = N OH (B)
(C)
(D) CH
3
(CH = CH)
3
Ph (E)
CH=CHCH
3
H
(F)CH
3
CCCH=CHCH
3
Q.5 Which of the following compound can show geometrical isomerism.
(A) C = C
Cl
Cl
Br
I
(B)
C
CH
3
CH
3
(C) C = C
Et
Et
F
Cl
(D)
C
CH
3
CH
3
CH
3
CH
3
Q.6 The geometrical isomerism is shown by
(A)
CH
2
(B)
CH
2
(C)
CHCl
(D)
CHCl
Q.7 Which of the following double bond will not exhibit geometrical isomerism.
(A)
C = C
Ph
C H
6 5
Me
CH
3
(B) C = O
Me
Ph
(C) C = N Me
Me
Ph
(D) Me N = N Me
N
.
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Q.8 Which of the compound show geometrical isomerism.
(A)
CH Br
Br
(B)
N
H
CH
3
(C)
N
H
O
(D)
N
CH
3
(E)
N
Cl
Me
H
(F)
N
Cl
Me
Me
(G)
N-H
COEt
O
N
Me
EtOC
O
(H)
N
N
H
N
(I)
O
N
H
COOMe
COOMe
NC
(J) H C = CH C
2
Me
Me
N
OMe
OCH Ph
2
(K)
C = C = C = C
Cl Cl
(CH ) C
3 3
(CH ) C
3 3
(L)
Br Cl
CH=CHCOOH
(M)
O
O
(N)
Q.9
Cl
Cl
The above conformation is
(A) cis
(B) trans
(C) will not show G.I. (D) cant predict
Q.10 for the boiling point of given compounds:
Cl
H
C = C
CH
3
H
Cl
H
C = C
CH
3
H
1
(A) 1 > 2
2
(B) 1 < 2
(C) 1 = 2
(D) none
(C) 1 = 2
(D) none
N
.
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Q.12 For which of the following keq > 1?
(A)
(B)
(C)
(D)
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP-10
Time: 2
0 Minutes
Q.1
Compound P.O.S. C.O.S. Optically active
1.
CH
3
CH
3
H H
2.
CH
3
CH
3
H
H
3.
CH
3
CH
3
H
H
4.
H
CH
3
H
CH
3
5.
H
Cl
H
Cl
6.
H
H
Cl
Cl
7.
H
H
Cl
Cl
Cl
Br
8.
Cl
H
Cl
H
Cl
H
N
.
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9.
C = C = C
H H
Cl
Cl
10.
C = C = C
H Cl
Br
Cl
11.
C = C = C = C
H H
Cl
Cl
12.
C
H
Cl
H
Cl
C
13.
C
H
Cl
Cl
H
C
14.
H
Cl
Cl
H
15.
3 CH
CH 3
H
H
16.
H
Cl H
Cl
17.
C
H
Cl
18.
H
C
CH
3
CH
3
H
N
.
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19.
H
C
CH
3
CH
3
Cl
20.
21.
22.
Cl
I
I
Cl
23.
24.
O = C = O
25.
O = C = O
H
26.
O = C = O
H
H
27.
N = N = N
H
H
28.
C
H
H
H
H
No. of POS _ _ _ _ _ _ _ _
29.
C
H
H
H
Cl
No. of POS _ _ _ _ _ _ _ _
N
.
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31
30.
No. of POS _ _ _ _ _
31.
No. of POS _ _ _ _
Q.2 Match the following structural formulae with their possible geometrical iso
mers?
Column-I
Column-II
(Structural formula (Total geometrical isomers excluding
mirror image)
(A) CH
3
CH = CH CH
2
CH
3
(P) 8
(B) CH
3
CH =
CH=CHCH
3
CH=CHCH
3
C
(Q) 6
(C) CH
3
CH = CH CH = CH CH
3
(R) 4
(D) Cl CH = CH CH = CH CH = CH CH
3
(S) 2
Q.3 Statement 1:
C = C
CH
3
H C
5 2
Br
Cl
and C = C
CH
3
H C
5 2
Br
Cl
are structural
Statement 2: The above mentioned compounds can show geometrical isomerism.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explan
ation for statement-1.
(B Statement-1 is true, statement-2 is true and statement-2 is NOT correct exp
lanation for
statement-1.
(C) Statement-1 is false, statement-2 is true.
(D) Statement-1 is true, statement-2 is false.
Q.4 Which compound(s) will show Geometrical isomerism?
(A)
CH
3
NH
(B)
C = C = C
H
Cl
H
Cl
(C)
H C
3
CH
3
(D)
O
O
H
H
N
N
Q.5 Find out the correct option(s) ?
(A)
C = C
H
CH
3
NH
NH
Orientation is E (B)
H
CH
3
CH
3
H
Orientation is Z
C = C
H H
CH
3
CH
3
C = C
H
H
CH
3
CH
3
N
.
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(C)
C = C
H
D
Orientation is Z (D)
CH
3
CH
3
geometrical isomers are not possible
Q.6 Calculate total number of geometrical isomers in following compounds. (Excl
uding mirror image)
(i) CH
3
CH = CH CH = CH CH = CH CH
3
(ii) CH
2
= HC CH = CH Me
(iii) Me CH = C = CH CH
2
CH = C = C = CH Me
(iv)
Me
D
(v)
(vi) Br CH = C = C = CH CH = CH Br
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
Date:
DPP- 11
Time: 15
minutes
Q.1 How many chiral carbon atoms are present in the following compounds?
(i)
H
N
O
H
H
CH
3
(ii)
O
O
S
PhOCH
2
C NH
N
COOH
Coccinellin
Penicillin V
(iii)
O
(iv)
COOH
HO
Estrone
Betulinic acid
Q.2 Assign priority number to the following groups as per Cahn, Ingold, Prelog
sequence rule
(a) CH
2
OH, CH
3
, CH
2
CH
2
OH, H
(b) Cl, Br, CH = CH
2
, CH
3
(c)
O
C H
, OH, CH
3
, CH
2
OH
(d) CH(CH
3
)
2
, CH
2
CH
2
Br, Cl, CH
2
CH
2
CH
2
Br
(e) CH = CH
2
, CH
2
CH
3
,
,
3
CH
(f) CH = CH
2
, C CH,
CH CH
2
CH
3
CH
3
C CH
CH
3
CH
3
CH
3
CH
3
(g) CH
2
CH
2
CH
2
I
CH CH CH
3
Br
CH CH
2
CH
3
Cl
F
Q.3 Indicate whether each of the following structure has the R configuration or
the S-configuration.
(a)
C
CH
3
CH
2
CH
3
CH
2
Br
CH(CH
3
)
2
(b)
C
CH
3
CH
2
CH
2
CH
2
Cl
CH
2
Br
OH
(c)
C
Cl
H
F
Br
(d)
C
H
OH
CH
2
Br
CH
3
(e)
C
CH
3
CH
2
H
D
CH
3
(f)
C
CH
3
CH
2
H
Br
CH
3
(g)
CH
2
CH
3
Cl
CH
3
H
(h)
CH
3
CH
2
Cl
F
H
(i)
CH =CH
2
CH
3
F
OH
(j)
SH
Me
H
NH
2
N
.
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(k)
CH
3
CH
2
CH
3
H
Cl
(l)
CH
2
CH
2
Br
H
NH
2
(m)
CH
3
CH
2
CH
3
H
CH
2
I
(n)
CHO
CH
2
OH
H
OH
(o)
CH
3
CH
2
CH
3
H
COOH
(p)
CH
3
CH
2
OH
HO
CH
2
CH
2
CH
2
OH
(q)
CH
3
CH
2
CH
3
HO
H
H
Cl
(r)
CH
3
CH
2
CH
3
Br
H
H
Br
(s)
CH
3
CH
2
CH
3
Br
H
H
Br
(t)
CH
3
CH
2
CH
3
H
Br
CH
2
CH
3
CH
3
(u)
OH
H
COOH
OH
H
COOH
Q.4 Indicate whether each of the following structure has the R configuration or
the S-configuration.
(a)
C
H
CH
3
COOH
CH = CH
2
(b)
C
CH
3
CH
2
CH
2
Cl
SH
CH
2
Cl
(c)
C
OH
CH
3
NH
2
F
(d)
C
D
OCH
3
T
CH
2
OH
(e)
C
CH
3
O
OCH
3
H
CH
3
18
(f)
C
HS
D
NH
2
I
(g)
DCH
2
SO
3
H
CH
3
SCH
3
(h)
CH
2
CH
3
CH
2
F
CH
2
OH
NH
2
(i)
CH
3
CH
2
CH
3
(j)
H
SR
Et
NR
2
(k)
CH
3
CH
2
CH
3
CH
2
CH
2
CH
3
I
(l)
CH
3
CH
2
OH
OPh
(m)
CH
3
H
D
CH
2
Cl
(n)
CH
3
COOH
H
OH
(o)
Me
Et
D
CHO
(p)
CH
2
NH
2
CH
2
CH
2
CH
2
NH
2
H
2
N
CH
2
CH
3
(q)
Me
CH
2
CH
2
CH
3
2
H
2
N
D
D
Br
(r)
CH
3
CH
2
CH
2
CH
3
2
I
Et
CH
3
I
(s)
CH
2
Cl
CH
2
CH
3
2
H
OMe
H
Br
(t)
CH
2
CH
3
CH
2
CH
3
2
CH
3
H
I
H
(u)
SO
3
H
H
Cl
SO
3
H
Cl
H
(v)
CH
2
CH
2
CH
2
COOH
H
CH
3
H
CH
3
(w)
Et
D
CH
2
CH
3
HO
Me
D
(x)
CH
2
CH
2
CH
3
H
Br
Cl
CH
2
CH
2
CH
3
H
(y)
COOH
OH
H
CH
2
OH
OH
OH
H
H
(z)
CH
3
H
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 12
Time: 15 min
utes
Q.1
Column-I
Column-II
(A)
O
Cl
Me
Me
Cl
(P) Total number of stereo isomers are odd.
(B)
Br
Br
(Q) Total number of stereocenter are even or have
centre
(C)
C
C
H
H
Cl
Cl
(R) Compounds having plane of symmetry or axis of
symmetry
(D)
HO
H OH
COOH
COOH
H
(S) Compounds have zero dipole in given form.
Q.2 Column-I
Column-II
(A)
Plane of symmetry
(P)
H
C
Me
Me
H
C
(B)
Me
Me
Centre of symmetry
(C)
H
Me
Me
Meso Compound
(Q)
(R) C
(S)
(T)
C = C = C = C
H
Cl
Cl
H
Comprehension (Q.3 to Q.5)
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On the basis of the following set of compounds, answer the following questions
.
(I)
H
OH
HO
H
CHO
H
CH OH
2
HO
OH
H
(II)
H
OH HOH C
2
HO
CHO
HO
H
HO H
H
(III)
H HO
H
CHO
H
CH OH
2
H
OH
OH
OH
(IV)
H
OH
HO
H
CHO
H CH OH
2
HO
OH
H
(V)
H HO
H
CHO
H
CH OH
2
HO H
HO
HO
Q.3 Which of the following represent enantiomeric pair?
(A) I & II
(B) II & V
(C) I & V
(D) II & IV
(E) III & V
Q.4 Which of the following does not represent active diastereomeric pair?
(A) III & IV
(B) I & II
(C) I & III
(D) I & IV
(E) None of these
Q.5 Which of the following represent D sugar.
(A) I
(B) II
(C) III
(D) IV
Q.6 Select the pair of enantiomer and diastereomers out of the following:
CH
3
CH
3
CH
3
H H
H
A
CH
3
CH
3
H C
3
H H
H
B
CH
3
CH
3
CH
3
H
H
H
C
CH
3
H C
3
H
H
H
D
H C
3
s
Q.7 Which of the following compounds should have the larger energy ba
rrier to rotation about the
indicated bond ?
(a) Me
3
C
|
CMe
(b) Me
3
Si
|
SiMe
3
Q.8 How many compounds are theoretically possible for formula C
3
H
6
O (excluding stereoisomers)?
Q.9 How many acyclic isomers of C
5
H
10
are possible which are incapable of showing Optical
Isomerism?
Q.10 How many stereoisomers are possible for the following?
CH=C=C=CHMe
Me
CH=CHCH=CH
2
Me
(A) 16
(C) 6
(B) 4
(D) 8
(D) 12
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.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
Date:
DPP NO- 13
Time: 15
minutes
Q.1
Column-I
Column-II
(A)
OH
OH
H
H CO H
2
CO H
2
(P) chiral
(B)
OH
OH
H
CO H
2
CO H
2
OH
(Q) achiral
(C)
H
H
CO CH CH OH
2 2 2
COH
2
(R) meso
(D)
CO CH CH O C
2 2 2 2
CO CH CH O C
2 2 2 2
H
H H
H
(S) compounds containing even number of chiral
center
Q.2 Column-I
(A)
Me H
Cl
Cl
and
Me
H
Cl
Cl
are
(B)
CH
3
H
CH
3
H
and
CH
3
H CH
3
H
are
(P)
Column-II
Structural isomers
(C)
C
C
CH CH COOH
2 2
Me
H
H
and
Et
C
C
Me
H
O
CH
3
C
O
are (R) Compounds which are
geometrical isomer and
diastereo isomers
(D)
OH H
COOH
H
COOEt
OH
and
H HO
COOH
HO
COOEt
H
are
(S) Compounds are
geometrical
isomers and enantiomers
(T) Not isomers
N
.
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Q.3 Statement 1:
F
F
F
F
(I)
(II)
(I) and (II) are optically inactive molecules.
Statement 2: Molecules containing plane of symmetry or centre of symmetry are
optically inactive.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explan
ation for statement-1.
(B Statement-1 is true, statement-2 is true and statement-2 is NOT correct ex
planation for
statement-1.
(C) Statement-1 is false, statement-2 is true.
(D) Statement-1 is true, statement-2 is false.
Q.4 Minimum C atoms required for a compound to show geometrical isomerism:
(A) 2
(B) 3
(C) 4
(D) None of these
Q.5 The correct stability order of the following species is
Me
Me
H
Me
H
H
H
Me
H
H
Me
Me
(a)
(b)
(A) c < a < b
(C) c < a = b
(c)
(B) c = b < a
(D) a = b = c
Q.6
Et
Me
This compound shows:
(A) geometrical isomerism
(C) both
(D) none
Q.7 (+)-Tartaric acid has a specific rotation of +12.0. Calculate the specific r
otation of a mixture of 68%
(+)-trataric acid and 32% ()- tartaric acid.
(A) 4.32
(B) 4.32
(C) 12
(D) 12
Q.13 How many geometrical isomers are possible for the following structure.
H
Q.14 Relationship between molecules:
(a)
C
H H
CH
3
CH
3
&
C
H H
CH
3
CH
3
(b)
C = C = C = C
H H
Cl Cl
&
C = C = C = C
H
H
Cl
Cl
(c)
CH
3
CH
3
Cl
&
CH
3
CH
3
Cl
(d) CH
3
CH
3
& CH
3
CH
3
N
.
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41
(e)
&
(f)
&
Q.15 Calculate total no. of optical isomers, optically, active, meso &
enantiomer pairs corresponding to
the following:
(a)
N
.
J
.
S
I
R
Meso compound
O
Me
OH
C C Me
Me
2
N
(RO486/mifepristone)
(Q)
(C)
H
O
O
H
N
H
O
(R)
(D)
H
OH
COOH
H
COOH
OH
(S)
(P)
Et
N
N
N
Et
Et
axis of symmetry
m
only)
(B) Compound having center of symmetry, plane of
(Q)
Me Me
symmetry and axis of symmetry
(C) Compound having axis of symmetry (C
3
)
:
N
(R)
N
.
J
.
S
2,2,3,3-Tetramethyl butane in
staggered conformer
I
R
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Question No.3 to 4 (2 questions)
Questions below consist of an "Assertion" in column I and "Reason"
in column II. Use the
following key to choose the appropriate answer
(A) If both " Assertion" and "Reason" are correct and "Reason" is
the correct explanation of the
"Assertion".
(B) If "Assertion" and "Reason" are correct, but "Reason" is not th
e correct explanation of the
"Assertion".
(C) If "Assertion" is correct, but "Reason" is incorrect.
(D) If "Assertion" is incorrect, but "Reason" is correct.
Q.3 Assertion : Cyclopropane is planar while cyclobutane is non-planar.
Reason : Angle strain in cyclopropane is more than that in cyclobutane.
Q.4 Assertion :
Me
Et
Me
is most stable of conformer of
Me
Me
Et
Reason : Torsional strain and flag pole interactions cause the boat
conformation to have
considerably higher energy than the chair conformation.
Q.5 Correct statement about D-mannitol (in given form) :
OH
HO
OH OH
OH
OH
(A) C
3
axis of symmetry (B) C
2
axis of symmetry
(C) Centre of symmetry is present (D) 3-chiral centre are present
Q.6 Which of the following pair of compounds can be separated by fractional cry
stallisation.
(A)
D
O
H
Me
O C
H
OH
Me
and
Me
O
D
H
O C
Me
H
OH
(B)
Cl
Cl
O
and
Cl
O
Cl
(C)
H
OH
COOH
HO
H
COOH
and
H
HO
COOH
HO
H
COOH
(D)
Me
Me
and
Me
Me
Q.7 An unknow compound weighing 4.5 gm is dissolved in enough carbon tetrachlor
ide to make a total
volume of 250 c.c. The observed rotation of this solution is +357.75
in a 25 cm cell using the
sodium D line. But if 4.5 gm is dissolved in 125 cc we observed ro
tation is +355.50. Calculate
specific rotation for this compound. (assuming length of polarimeter tube is 1 d
m)
Q.8 Identify chiral and achiral compounds from the list given below :
(a)
Br
F
Br
F
(b)
I
C = C = C
Cl
(c)
Cl
Cl
(d)
OH
CO
2
H
H
H
CHO
OH
(e)
NO
2
SO
3
H
NO
2
SO
3
H
(f)
H
CH
3
CH
3
H
CH3
H
N
.
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44
(g)
Me
Me
Et
Cl
H
H
H
H
(h)
C = C
CH
3
H H
CH
3
(i)
CH
3
CH
3
N N
CH
3
CH
3
CO
2
H
HO
2
C
(j)
HO
2
C
CO
2
H
CO
2
H
HO
2
C
H
5
C
6
C
6
H
5
N
N
(k)
N
C
6
H
5
H
H
5
C
2
O
2
C
H
(l)
C
H
3
C
C
CH
3
C
C
C
O
H
H
CH
3
H
(m)
C = C = C = C
NO
2
NO
2
Q.9 Calculate the specific rotations of the following samples taken at 25 using
the sodium D line.
(a) 1.00 g of sample is dissolved in 20.0 mL of ethanol. Then 5.00 mL of this
solution is placed in a
O
H
HO
2
C
(v)
HO
2
C
N = N
CO
2
H
(Azodiformic acid)
(vi)
CH
3
CH
3
(vii)
Cl
CH
3
CH
3
(viii)
CH
3
CH
3
(ix)
CH
3
CH
3
CH
3
CH
3
N
.
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IIT-JEE Chemistry by N.J. Sir
DPP-15
utes
Q.1 Match the following :
Column I
Column II
(A)
ORGANIC chemistry
H C
H
Cl
(P) It can show geometrical isomerism
(B)
C
H
CH
3
CH
3
H
O
NH
O
NH
(R) Presence of odd, number of chiral carbon
(D)
C = C C C = C
Br
H H
Br
H H Br
H
(S) Resolvable compound
(T) Presence of Pseudo chiral centre
Q.2 Match the following :
Column I
Column II
(A)
Time: 15 min
OH
O
H
H
CH
3
(P)
(B)
H
CH
3
C
CH
2
H
CH
3
O
(Q)
(C)
OH
H
CO
2
H
OH
H
CO
2
H
(R) Odd number of chiral centre
(D)
HO
H
CH
2
NH
2
HO
OH
(S)
H
3
C
CH
3
H
F
(A)
OH
Br
Cl
CH
3
H
3
C
F
H
F
(B)
OH
Br
Cl
H
3
C
F
H
F
H
3
C
(C)
OH
Br
Cl
CH
3
F
H
F
H
3
C
(D)
OH
Br
Cl
F
H
F
H
3
C
H
3
C
OH
HO
H
N
O
CH
3
CH
3
(II)
OH
HO
H
N
O
CH
3
CH
3
(III)
OH
HO
H
N
O
CH
3
CH
3
(IV)
OH
HO
H
N
O
CH
3
CH
3
(V)
OH
HO
H
N
O
CH
3
CH
3
(VI)
OH
HO
H
N
O
CH
3
CH
3
N
.
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Establish the stereochemical relationship between : (a) I and II, (b) III and
IV, (c) II and III, (d) I and
V, (e) IV and (VI)
(v)
2
Me
MeCHBrCH
(vi)
Me
Br
N
..
Me
(vii)
H
Cl
N
..
Me
(viii)
Me
O
Me
N
(ix)
MeN DH
2
Br
O
(x)
MeCH
2
CHCH
2
Me
OH
(xi)
NO
2
SO
3
H
NO
2
SO
3
H
(xii)
C = C = CH
2
H
Cl
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 16
Time: 1
5 minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
(1)
(a)
(b)
(2)
OH
OH
OH
OH
OH
OH
(a)
(b)
(3)
CO H
2
CO H
2
(a)
(4)
H
H
Me
Me
H H
Me Me
(b)
(c)
(a)
(b)
(5)
H
H
(a)
(b)
(6)
OH
OH H
H
Me
Et
H
H HO
HO
Me
Et
(a)
(b)
(7)
Br Br
Cl Cl
Br Br
Cl Cl
(a)
(b)
(8)
N
.
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(a)
(b)
Identical
isomer
(9)
OH
OH
(a)
(b)
(10)
OH
O
OH
O
(a)
(b)
(11)
H
NH
2
COOH HO
HO
(a)
H
NH
2
HOOC
OH
OH
(b)
(12)
(a)
(b)
(13)
Cl
Cl
(a)
(b)
(14)
O
Cl
H
O
Cl
H
(a)
(b)
(a)
(15)
O
SO
O
Me
(b)
(a)
O
OS
O
Me
(b)
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 17
Time: 15
minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
(1)
Cl
Cl
(a)
(b)
(2)
N
N
(a)
(b)
(3)
H
H
Me
OH
O
H
Me
Me
O
O
(a)
(4)
OH
(b)
OH
COOH
COOEt
H
H
H
H HO
HO
COOH
COOEt
(a)
(b)
(5)
H Me
Cl Cl
H
Me
Cl Cl
(a)
(b)
(6)
OH
H
OH
H
(a)
(b)
(7)
H H
H
Me
Br
H
H
H
Br
(a)
(8)
SH
OH
Me
Et
H
H
H
H
Me
Et
HS
HO
(b)
N
.
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(a)
(b)
Identical
er
isomer
(9)
Cl
Cl
Cl
Cl
Cl
Cl
(a)
(b)
(10)
O
N
H
OH
N
(a)
(b)
(a)
(b)
(11)
(12)
H
H
Me
H
H
Me
(a)
(b)
Enantiomer
(13)
Cl
Br
Cl
Br
(a)
(b)
(14)
H
HO
OH
H
HO
OH
(a)
(b)
(15)
Cl
Et
H
H
Cl
Cl
Et
H
H
Cl
(a)
(b)
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 18
Time: 1
5 minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
(1)
H C = N
2
CH = NH
O
O
(a)
H C = N
2
CH = NH
O
O
(b)
(2) C
O
H
Me
OH
(a)
C
O
H
Me
OH
(b)
(3)
CN
Br
OH
COOH
H
H
CN
Br
HO
COOH
H
H
(a)
(b)
(4)
O
Br
O
Br
(a)
(5)
Br
Br
H
H
Br
Br
Me
H
(b)
H
(a)
(b)
(6)
O
OH
(a)
(b)
N
.
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Identical
Enantiomer
isomer
(7)
CH
3
H
OH
CH
3
OH
H
CH
3
H
H
CH
3
OH
HO
(a)
CH
3
HO
OH
CH
3
H
H
(b)
(c)
(8)
(a)
(b)
(9)
CO H
2
H
OH
CO H
2
OH
H
CO H
2
H
CO H
2
HO
H HO
(a)
(b)
(10)
Me
Et
Me
Et
(a)
Et
Et
Me
Me
(b)
(11)
O
O
(a)
O
O
(b)
N
.
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Enantiomer
isomer
(12) N
N
(a)
(b)
(13) N
N
(a)
(b)
(14)
I
Cl
Br
I
Cl
Br
(a)
(b)
(15)
O
O O
O
(a)
O
O
O
O
(b)
O
O
O
O
(c)
(16)
NH Me
NH
2
(a)
NH
(b)
2
NH
(c)
(d)
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 19
Time: 1
5 minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
(1)
OH
O
(a)
(b)
OH
(c)
(2)
N
H
O
N
OH
(a)
(b)
(3)
OH
O
(a)
(b)
OH
OH
(c)
(d)
(4)
(a) (b)
(c)
(5)
N
Me
O
N
OH
(a)
(b)
(6) Me C N Me N
C
(a)
(b)
(7)
OH
OH
(a)
(b)
N
.
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Identical
isomer
(8)
OH
O
OH O
H
(a)
(b)
O
H
O
(c)
Enantiomer
(9)
O
O
(a)
(b)
(10) CH
3
OH
OH
(a)
(b)
(11)
OH
CH
3
OH
(a)
(b)
(12)
Cl
Cl
Cl
Cl
(a)
(b)
(13)
CN
CN
(a)
(b)
(14)
CO H
2
CO H
2
(a)
(b)
(15)
(a)
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 20
5 minutes
If there is presence of given symmetry then writes (\) otherwise (x)
Compound
P.O.S(s) C
2
C
3
S
4
S
2
(1)
N
(2)
Cl
(3)
C
C
C
H
H
H H
(4)
(5) C
Br
CH
3
CH
3
CH
3
(6)
CH
3
CH
3
(7)
Br
Br
Br
Br
Time: 1
Br
Br
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 21
Time: 1
5 minutes
If there is presence of given symmetry then writes (\) otherwise (x)
Compound
P.O.S(s) C
2
C
3
S
4
S
2
(1)
(2)
(3)
O
(4)
(5) C = C
Cl Cl
H
H
(6)
C = C
Cl
Cl H
H
(7)
H
H
Br
Br
(8)
CO H
2
H
CO H
2
HO
OH H
(9)
(10)
N
.
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IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 22
Time: 1
5 minutes
1. Find (m) meso compounds & optically active (a) and total stereoiso
mer
(a + m) of following
compounds
Compound
Meso (m) Active isomer (a)
(a + m)
(1)
CH
3
CH
3
H C
3
H C
3
(2)
Br
Cl
Cl
(3)
(4)
N
H
Cl
Cl
(5)
CH
3
H C
3
Cl
Cl Br
Br
(6)
O
O
Cl
Cl
Cl
Cl
OH
HO
(7)
Cl
CH
3
H C
3
(8) H C
3
CH
3
Cl
H C
3
O
O
(9)
N
.
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Compound
(a + m)
(10)
(11)
Br
Br
(12)
Br
Cl
(13)
C
CH
3
H C
3
H H
(14)
Cl
Cl
Cl
Cl Cl
Cl
(15)
CH
3
CH
3
H C
3
H C
3
(16)
H C
3
HN
CH
3
Br
CH
3
CH
3
H
3
C
N
.
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F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
61
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 24
Time: 1
5 minutes
1. Find (m) meso compounds & optically active (a) and total stereoiso
mer
(a + m) of following
compounds
Compound
Meso (m) Active isomer (a)
(a + m)
(1)
(2)
CH
3
Cl
Cl
(3)
(4)
Cl
CH
3
Br
CH
3
Br
(5)
Br
Br
Br
(6)
H C
3
Cl
CH
3
Cl
CH
3
SH
Br
(7)
CH
3
H C
3
(8)
CH
3
H C
3
Cl
Cl
CH
3
CH
3
Cl
N
.
J
.
S
I
R
--------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
62
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 24
Time: 1
5 minutes
1. Find (m) meso compounds & optically active (a) and total stereoiso
mer
(a + m) of following
compounds
Compound
Meso (m) Active isomer (a)
(a + m)
(1)
(2)
Cl
Cl Cl
Br
(3)
Cl
CH
3
CH
3
(4)
(5)
OH
CH
3
H C
3
HO
(6)
Cl
Br
(7)
CH
3 CH
3
Cl Cl
(8)
CH
3 CH
3
Cl Br
(9)
OH
Cl
O
O
Cl Cl
Cl
Cl Cl
Cl
Cl
HO
OH
CH
3
HO
3
N
.
J
.
S
I
R
--------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
63
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 25
Time: 1
5 minutes
1. Find (m) meso compounds & optically active (a) and total stereoiso
mer
(a + m) of following
compounds
Compound
Meso (m) Active isomer (a)
(a + m)
(1)
Cl Cl
(2)
H C
3
CH
3
Cl
Br
(3)
CH
3
CH
3
(4)
Cl
CH
CH
(5)
(6)
CH
2
CH
2
(7)
CH
3
H C
3
(8)
CH
3
H C
3
CH
3
H C
3
CH
3
H C
3
(9)
Br
H C
2 CH
3
(10)
HO
H C
3
CH
3
(11)
OH
Cl
O
O
Cl Cl
Cl
Cl Cl
Cl
Cl
HO
N
.
J
.
S
I
R
--------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
64
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 26
Time: 1
5 minutes
1. Identify correct matching and find out the total number of chiral centre.
S.No. Compound Optically active Chiral Achiral Optically
No. of
molecule molecule inactive
Chiral Center
(1)
N
Et
(2)
C
Me
Me
(3)
COOH
H
HO
(4)
S
Me
O
(5)
OH
OH
(6)
H
OH
OH
H
(7)
Cl
Cl
(8)
O
OH
HO OH
OH
HO
N
.
J
.
S
I
R
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F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
65
S.No. Compound Optically active Chiral Achiral Optically
No. of
molecule molecule inactive
Chiral center
(9)
H
Me
H
Cl
Cl
Me
(10)
H
O O
H
Me
Me
O
O
(11)
Cl Cl
H
H
CH OH
2
CH OH
2
(12)
O
Me
Me
(13)
Br
Cl
F
(14)
(15)
Me
H
H
Cl
Cl
Me
(16)
Me
Me
H
H
Br
Br
N
.
J
.
S
I
R
--------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
N
.
J
.
S
I
R
--------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
67
S.No. Compound Optically active Chiral Achiral Optically
No. of
molecule molecule inactive
Chiral Center
(9)
C = C = C = C
Me
Me H
H
(10)
CO CH
2 2 2
CO CH
2 2 2
H
H H
H
CH O C
2
CH O C
2
(11)
H
H
OH
HO CO H
2
CO H
2
(12)
CO CH CH OH
2 2 2
CO H
2
H
H
(13)
H
OH
CO H
2
CO H
2
H
OH
(14)
NH
HN
O
O
H
H
Me
Me
(15)
NH
HN
O
O
H
H
Me
Me
(16)
Cl
Cl
H H
N
.
J
.
S
I
R
--------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
68
IIT-JEE Chemistry by N.J. Sir
ORGANIC chemistry
DPP NO- 28
Time: 1
5 minutes
1. Identify correct matching and find out the total number of chiral centre.
S.No. Compound Optically active Chiral Achiral Optically
No. of
molecule molecule inactive
Chiral Center
(1)
COOH
COOH H
H
H
H
Ph
Ph
(2)
H H
COOH
Me
(3)
H
H
COOH
Me
(4)
Br
F
Br
F
(5)
C = C = C
Cl
I
(6)
(7)
Cl
Me
Me
(8)
(9)
Me
Me
Me
Me
N
.
J
.
S
I
R
--------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahind
ra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
69
S.No. Compound Optically
Chiral Achiral Optically No. of
active
molecule molecule inactive Chiral center
(10)
H
H
H
Me Me
(11)
Cl
Cl
(12)
Cl
Me
Me
Me
Me
COOH
Br
(13)
Me
Me
Me
Br Me
Me Me
Br
Br H H OH
Br OH
(14)
H
D
Me
COOH
(15)
O
(16)
H
N
N
O
HO C
2
C H
6 5
(17)
CH
3
CH
3
Cl
Cl H
H