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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry


























CONCEPTUAL IMPROVEMENT
OF ISOMERISM


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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP-1 Time: 20 Minutes
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 are _ _ _ _ _ _ _
(c)
H
CH
3
C = C
H
O

&
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 Column II
(A)
N
CH
3
H
& CH
2
NH
2
(P) metamers
(B) H
O
||
C

OCH
3
& CH
3

O
||
C

OH (Q) functional isomers
(C)

& (R) position
(D)

&
PhOCO
H
H
C = C
H
O
(S) identical















H
H
C = C
H
O
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5


IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 2 Time: 15 minutes
Compounds Relationship

1. &

2.
O
&
O


3. &

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



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6


Compounds Relationship
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

&
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





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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 3 Time: 15 minutes
Q.1 Which of following is 2 alcohol ?
(A)
OH
(B)
OH
(C)
OH
(D)
OH


Q.2 Which of following is 3 alcohol ?
(A)
OH
(B)
OH
(C)
OH
(D)
OH


Q.3 Which of following is 2 amine ?
(A)
NH
2
(B)
NHCH
3
(C)
N
CH
3
(D)
NH
2


Q.4 Which of following compound has presence of 1, 2, 3, 4 carbon ?
(A)

(B)

(C) (D)

Q.5 How many ether is/are possible for molecular formula C
4
H
10
O.
(A) 1 (B) 2 (C) 3 (D) 4

Q.6 How many ketone is/are possible for molecular formula C
4
H
8
O
(A) 1 (B) 2 (C) 3 (D) 4

Q.7 How many alcohol is/are possible for Molecular farmula C
4
H
10
O (only structural)
(A) 2 (B) 3 (C) 4 (D) 5
Q.8
OH
O
O

Number of Functional group in above compound is
(A) 3 (B) 4 (C) 5 (D) 6


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Q.9 The functional groups in Cortisone are:
O
O
HOH C
2
CH
3
OCH
3
Cortisoe

(A) Ether, alkene, alcohol (B) Alcohol, ketone, alkene, ether
(C) Alcohol, ketone, amine (D) Ether, amine ketone

Q.10
O
O
O H
SH
OH
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

Q.14 Present functional group is
O
O CH
3
CH
3

(A) ketone (B) ester (C) ether (D) alcohol

Q.15 Present functional group is/are
O
O
OCCH
3
O

(A) ketone (B) ester (C) ether (D) A and B both
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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 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
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O O
|| ||
(f) C H (g) C OH
| |
C H C OH
|| ||
O O

Q.4 Which of the following is the staggered conformation for rotation about the C
1
C
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 conformation 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 potential 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 stabilities 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 (B) I has more steric strain
(C) II has more torsional strain (D) II has more steric strain

Q.8 Draw the Newman projection that represents the least stable conformation 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-bromopropane considering
rotation about the C
1
C
2
bond.

Q.10 Draw a Newman projection of the most stable conformation of 2-methylpropane.

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 represented at
which point

A
B
C
D
E
angle of rotation

(A) A (B) B (C) C (D) D

Q.14 If for 1,2-dibromoethane is 0.75 D and X
anti
= 0.7 Calculate for gauche.


Q.15 Compare relative stabilities of given conformers.
(a)
H
H
H
H
CH
3
CH
3
(b)
H
H
H
H
CH
3
CH
3
(c)
H
H
H
H
CH
3
CH
3



Q.16 Draw most stable conformer of
(a) 3-methyl pentane
(b) 3-methyl hexane

Q.17 Draw most stable forms of
Z CH
2
CH
2
OH
Z = OH, F, Cl, NH
2
, OMe,
O
||
C
OH,
O
||
C
H

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Q.18 (Me
3
) N

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 temperature 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) (iii)
(b)
CH CH
2 2

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 | o | o | o |
(1) (2) (3) (4)
(d)

(i) (ii) (iii)
(e)


(i) (ii)




CH CH
CH
3
CH
3
CH CH
2 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) C O C bond angle in cation. ..
(B) C O C bond angle in neutral molecule .
(C) C O C C dihedral angle in the cation
(D) C O C C dihedral angle in the neutral molecule..

Q.2 Which of the following is the most stable conformation of bromocyclohexane?
(I)
H
Br
(II)
H
Br
(III)
Br
H
(IV)
Br
H


(V)
H
Br

(A) I (B) II (C) III (D) IV (E) V

Q.3 Which of the following correctly lists the conformations of cyclohaxane in order of increasing
energy?
(A) chair < boat < twist-boat < half-chair (B) half-chair < boat < twist-boat < chair
(C) half-chair < twist-boat < boat < chair (D) chair < twist-boat <boat < half-chair

Q.4 In the boat conformation of cyclohexane, the flagpole hydrogens are located:
(A) on the same carbon (B) on adjacent carbons
(C) on C-1 and C-3 (D) on C-1 and C-4
(E) none of the above

Q.5 The K
eq
for the interconversion for the two chair forms of methylcyclohexane at 25C is 18. 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-3-
methylcyclohexane
(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 (B) cis-1, 2-dichlorocyclohexane
(C) trans-1, 3-dichlorocyclohexane (D) cis-1, 3-dichlorocyclohexane
(E) trans-1, 4-dichlorocyclohexane




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Q.8 What can be said about the magnitude of the equilibrium constant K for the following process?

H
H
H
H
CH
3
CH
3
CH(CH )
3 2
CH(CH )
3 2

(A) K = 1 (B) K > 1
(C) K < 1 (D) No estimate of K can be made


Paragraph for Question Nos. 9 to 11

Groups bonded by only a sigma (o) bond (i.e., by a single bond) can undergo rotation about that
bond with respect to each other. The temporary molecular shapes that result from rotation of groups
about single bonds are called conformations of a molecule. Each possible structure is called a
conformer. An analysis of the energy changes associated with a molecular undergoing rotation
about single bonds is called conformational analysis.

Q.9 Most stable conformer of given compound is

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)

Q.11 Which of the following pairs of structures represent conformational isomers?
(A) (B)
H H
H H
CH
3
CH
3
H H H
H CH
3
CH
3


(C)
Cl Br
Cl
Br

(D)



H
H
H
H
H
H
H
H
H
H H
H
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Q.12 Which of the following pairs of structures represent conformational isomers?
(A) and (B)

and
(C) and (D)
C
and
C



Q.13 Draw the Newmann projection formula of the most stable conformation of 3-hydroxy propanal
across C
2
and C
3
.

Q.14 (a) Below are six conformations for a specific compound. With respect to the biggest groups,
determine which structure are eclipsed, anti, gauche, highest in energy and lowest 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) and



(f) and


(g)

and



(h)

and



Q.6 Draw 1,2,3,4,5,6-hexamethyle cyclohexane in which all
(a) methyl at axial position (b) methyl at equitorial position.

Q.7 Draw most stable form of methyl-cyclohexane.


OH
HO
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Q.8 Compare stability of the following:
(a) (b)
(c) (d)

Q.9 Draw structure & compare stabilities of following
(a) cis & trans 1, 2 dimethyl cyclohexane.
(b) cis & trans 1, 3 dimethyl cycohexane.

Q.10 Explain:

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 Time: 15 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
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


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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
3

O
||
C NH CH
3

(C)
O
||
C NH CH
3
(D)
CN
Me
Me
O


3. Write cis/trans in the following of it show G.I.
(A)
CH
3
CH
3
C
(B)
Cl
Cl

(C)
Cl
Cl


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(D) (E) (F)

(G)


(H)
Cl
Cl
(I)
Cl
Cl


(J)
Cl
Cl

(K)
Cl
Cl
(L)
Cl
Cl



4. Following will show G.I.
(A)
C
CH
3
H
(B)
C
H
H
(C)
C
H
H
(D)
C
CH
3
H





















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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) (4)
(5)

(6)
(7)

(8)
(9) (10)
(11)
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)
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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 (D) cant predict




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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


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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 2
(A) 1 > 2 (B) 1 < 2 (C) 1 = 2 (D) none

Q.11 For the melting point of given compounds

Et
H
C = C
CH
3
H

Et H
C = C
CH
3
H

1 2
(A) 1 > 2 (B) 1 < 2 (C) 1 = 2 (D) none


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Q.12 For which of the following keq > 1?
(A)

(B)

(C)

(D)



























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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP-10 Time: 20 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


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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


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19.

H
C
CH
3
CH
3
Cl


20.



21.



22. Cl
Cl
I
I


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 _ _ _ _ _ _ _ _

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30.


No. of POS _ _ _ _ _


31.

No. of POS _ _ _ _



Q.2 Match the following structural formulae with their possible geometrical isomers?
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 explanation for statement-1.
(B Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation 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
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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. (Excluding 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



























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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
,

, CH
3

(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

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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





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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 12 Time: 15 minutes
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) Centre of symmetry (Q)
Me
Me


(C) Meso Compound (R) C
H
Me
Me


(D) Chiral atom is / are present (S)
H H
H
H Ph
Ph
C
O
O
H
COOH


(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 barrier 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 (B) 4

(C) 6 (D) 8

Paragraph for question nos. 11 to 13
Answer the following questions based on given reaction
Cl
2
hv
(monochlorination)
Products.

Q.11 The number of theoretically possible products (including stereo) are

(A) 6

(B) 8

(C) 10 (D) 12

Q.12 How many products are resolvable.
(A) 4 (B) 6 (C) 8 (D) 10
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Q.13 How many factions are present on fractional distillation?
(A) 4 (B) 5 (C) 6 (D) 8

Q.14
(a) How many plane of symmetry are present in prismane (C
6
H
6
)?

(b) How many chiral centres are present in the following compound?
O
S
O
Ph
Br

(c) Minimum carbon atoms required for an alkane to show optical isomerism.





























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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 Column-II
(A)
Me H
Cl
Cl

and
Me
H
Cl
Cl
are (P) Structural isomers
(B)
CH
3
H
CH
3
H
and
CH
3
H CH
3
H
are (Q) Compounds are optical
isomers and enantiomers
(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

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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 explanation for statement-1.
(B Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation 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) (c)
(A) c < a < b (B) c = b < a

(C) c < a = b (D) a = b = c

Q.6
Et
Me
This compound shows:
(A) geometrical isomerism (B) optical isomerism

(C) both (D) none

Q.7 (+)-Tartaric acid has a specific rotation of +12.0. Calculate the specific rotation of a mixture of 68%
(+)-trataric acid and 32% ()- tartaric acid.

(A) 4.32

(B) 4.32 (C) 12 (D) 12

Paragraph for question nos. 8 to 10
24 gm of optically pure tartaric acid is dissolved in water to make 240 ml solution. It is kept in 20 cm
polarimeter tube & plane polarized light is passed through it to product rotation of 2.4.
Q.8 If mixture of d and l tartaric acid has the specific rotation 4.0, calculate the % of optical purity of
this mixture?
(A) 50% (B) 66.67% (C) 33.33% (D) None

Q.9 Calculate the % of d tartaric acid in a mixture of d and l tartaric acid which has the observed specific
rotation + 6.0.
(A) 25% (B)75% (C) 50% (D) 66.67%

Q.10 If original solution is diluted by 2 times and length of polarimeter is increased four times of previous
length. What will be the specific rotation.
(A) 4.8 (B) + 4.8 (C) 6 (D) 12

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Q.11 Select resolvable compounds.
(A)
HO
O
H
N
CH
3
(B)
Cl
OH
O

(C)
H
(D)
CH
3
H
NH
H
O
Me
O
O


Q.12 Calculate total number of stereocentre, prochiral carbon and theoretical stereoisomer in the
following compound.
S
N
O

Number of stereocentre =v ; Number of prochiral carbon =x and number of stereoisomer =
yz. Represent your answer as vxyz. For example v =4, x =4 and yz =34 so represent it as
4434.

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

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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)




























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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP-14 Time: 15 minutes

Q.1 Match the following :
Column I Column II
(A)

Me

O

Me
C Me

O

Progesteron

(P) Meso compound
(B)

O

Me

OH

C C Me

Me
2
N

(RO486/mifepristone)

(Q) Compound having even no. of chiral carbon
(C)

H

O

O

H

N
H

O

(R) Optically active compound

(D)

H

OH

COOH

H

COOH

OH

(S) Compound having odd no. of chiral carbon
(T) Compound having odd no. of prochiral carbon.

Q.2 Match the following :
Column I Column II
(A) Compound having only plane symmetry and (P)

Et
N
N
N
Et
Et

axis of symmetry (Consider the given chair form
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
) (R)
:
N



(D) Compound having C
2
axis of symmetry but absence (S) 2,2,3,3-Tetramethyl butane in
of plane of symmetry staggered conformer




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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 the 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 crystallisation.
(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 tetrachloride 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 rotation is +355.50. Calculate
specific rotation for this compound. (assuming length of polarimeter tube is 1 dm)

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

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(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
20.0 cm polarimeter tube. The observed rotation is 1.25 counterclockwise.
(b) 0.050 g of sample is dissolved in 2.0 mL of ethanol, and this solution is placed in a 2.0 cm
polarimeter tube. The observed rotation is clockwise 0.043.
(c) Indicate the stereo centres in the following molecule and total number of stereomers in the
following molecule. Also draw the structures of pair of distereomers.


COOH

H
N
H

N

O

O


Q.10 Select chiral molecule out of the following list compound.
(i)

CH
3
O

(ii)

H

H

H

OH

COOH

HO

HO

HOOC


(iii)

C = C = C
(iv)

N
N
C
C
6
H
5

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


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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP-15 Time: 15 minutes
Q.1 Match the following :
Column I Column II
(A)

H C
H
Cl
(P) It can show geometrical isomerism
(B)
C
H
CH
3

CH
3

H (Q) Optically active compound
(C)


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)

OH
O

H

H

CH
3
(P) Total number of stereoisomers is odd for the structure
(B)


H

CH
3
C

CH
2
H

CH
3
O

(Q) Total number of stereoisomers is even for the structure
(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) Even number of chiral centre
(T) Optically active diastreomers possible
(U)
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 the correct explanation of the
"Assertion".
(C) If "Assertion" is correct, but "Reason" is incorrect.
(D) If "Assertion" is incorrect, but "Reason" is correct.
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Q.3 Assertion :

CH
3
Cl

O

Cl

CH
3
is an optically active compound.
Reason : No symmetry element is present in above compound.

Q.4 Assertion : Cis form of 1, 3-dimethyl cyclohexane is more stable than its trans form.
Reason : Heat of combustion of trans form of 1,3-dimethyl cyclohexane is more compared to its cis
form.

Q.5 Which of the following Fischer projection is the enantiomer of the following molecule ?

Cl

Br
F

HO

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



Q.6 How many plane of symmetry are present in following compound.


(A) 2 (B) 1 (C) 0 (D) 3

Q.7 (i) The specific rotation of (S)-2-iodobutane is +15.90.
(a) Draw the structure of (S)-2-iodobutane
(b) Predict the specific rotation of (R)-2-iodobutane
(c) Determine the percentage composition of a mixture of (R) and (S)-2iodoobutane with a
specific rotation of 7.95.
(ii) Dextrorotatory o-pinene has a specific rotation | |
20
D
o = + 50. A sample of o-pinene containing
both the enantiomers was found to have a specific rotation value | |
20
D
o = 30. The percentage
of the (+) and () enantiomers present in the sample are, respectively.

Q.8 Consider the following six structures :
(I)

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


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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)




Q.9 Select resolvable compounds
(i)

Br
I
Br I
(ii)

NO
2
SO
3
H
NO
2
SO
3
H


(iii)

Ph S = O
CH
3

(iv)

N

N
Me

Me



(v) MeCHBrCH
2
Me (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














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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 16 Time: 15 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) (c)

(3)
CO H
2

CO H
2
(a) (b)

(4)
H
H
Me
Me

H H
Me Me

(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 Enantiomer Diastereomer Constitutional Other
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) (b)

(15)
O
SO
O
Me

(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) (b)

(4)
OH
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) (b)

(8)
SH
OH
Me
Et
H
H

H
H
Me
Et
HS
HO

N
.
J
.

S
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(a) (b)

Identical Enantiomer Diastereomer Constitutional Other
isomer

(9)
Cl
Cl
Cl

Cl
Cl
Cl

(a) (b)

(10)
O
N
H

OH
N

(a) (b)

(11)


(a) (b)

(12)
H
H
Me

H
H
Me

(a) (b)

(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
.
J
.

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52

IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 18 Time: 15 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) (b)

(5)
Br
Br
H
H
Br
Br
Me
H
H

(a) (b)

(6)
O

OH

(a) (b)
N
.
J
.

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Identical Enantiomer Diastereomer Constitutional Other
isomer

(7)
CH
3
H
OH
CH
3
OH
H

CH
3
H
H
CH
3
OH
HO

(a) (b)
CH
3
HO
OH
CH
3
H
H

(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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Identical Enantiomer Diastereomer Constitutional Other
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) (b)

NH
2

NH

(c) (d)
N
.
J
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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 19 Time: 15 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
.
J
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Identical Enantiomer Diastereomer Constitutional Other
isomer

(8)
OH
O

OH O
H

(a) (b)
O
H
O

(c)

(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) (b)



N
.
J
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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 20 Time: 15 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
Br
Br




N
.
J
.

S
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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 21 Time: 15 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
.
J
.

S
I
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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 22 Time: 15 minutes
1. Find (m) meso compounds & optically active (a) and total stereoisomer (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
.
J
.

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Compound Meso (m) Active isomer (a)

(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
.
J
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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 24 Time: 15 minutes
1. Find (m) meso compounds & optically active (a) and total stereoisomer (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
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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 24 Time: 15 minutes
1. Find (m) meso compounds & optically active (a) and total stereoisomer (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
.

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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 25 Time: 15 minutes
1. Find (m) meso compounds & optically active (a) and total stereoisomer (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
.

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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 26 Time: 15 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
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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
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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 27 Time: 15 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)
Me
Me

(2) Me
Me
H
H

(3)
NO
2
NO
2 F
COOH

(4)
Cl Cl
F F

(5)
Me
Me
Cl
Cl
Cl H
H
H

(6) O = C = O

(7) C C
Br
Br
H
H

(8)
C = C = C = C
NO
2
Me Cl
F



N
.
J
.

S
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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 CH O C
2 2 2 2
CO CH CH O C
2 2 2 2
H
H H
H

(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
.

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IIT-JEE Chemistry by N.J. Sir ORGANIC chemistry
DPP NO- 28 Time: 15 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
.

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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