Isomerism DPP PDF

IIT-JEE Chemistry by N.J.
Sir ORGANIC chemistry
IR
.S
CONCEPTUAL IMPROVEMENT
OF ISOMERISM
.J
N
1
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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) &
IR
(d) CH2 — OH & O — CH3
(e) &
.S
(f) &
(g) &
.J
COOH
COOH
(h) OH &
OH
N
(i) &
H
(j) CH3 — CH2 — CH2 — NH2 & CH3—CH2 — N
CH3
(k) O — CH3 & CH2 — OH
2
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OH CH2—OH
(l) CH3 &
(m) & CH3 — C  C — CH3
CH3
(n) CH3 — CH2 — CH2 — CH2 — NH2 & CH 3— CH2 — N

CH 3
O O
CH2—C — OH C — O — CH3
(o) &
IR
(p) &
(q) &
.S
(r) &
Q.2 Fill in the blanks:–

O O
(a) —C—O— & —C—O— are _ _ _ _ _ _ _
.J
(b) —O— & —O— are _ _ _ _ _ _ _
O O
N
(c) H & H are _ _ _ _ _ _ _

C=C C=C
CH3 H CH3 H
(d) CH3 — CH2 — CH2 — N — CH3 & CH3 — CH2 — N — CH2 — CH3 are _ _ _ _ _ _ _
| |
H H
(e) CH3 — CH2 — CH2 — C  N & CH3 — CH2 — CH2 — N 

 C are _ _ _ _ _ _ _
3
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(f) CH2 — SH & S — CH3 are _ _ _ _ _ _ _
O O
||
(g) CH3— CH2—CH2—C & CH3 — CH2 — C — CH3 are _ _ _ _ _ _ _
H
O O
||
(h) CH3— CH2—CH2—C & CH3 — CH2 — C — CH2 — CH3 are _ _ _ _ _ _ _
CH3
Q.3 Column matching

Column I Column II
H
(A) —N & CH2 — NH2 (P) metamers
IR
CH3
O O
|| ||
(B) H — C — OCH3 & CH3 — C — OH (Q) functional isomers
.S
(C) & (R) position
O
O
H
(D) C=C & PhO—C—O H (S) identical
H H C=C
.J
H H
N
4
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DPP NO- 2 Time: 15 minutes
Compounds Relationship
1. &
O
2. &
O
3. &
IR
4. &
Cl Br
.S
5. &
Br Cl
6. CH2 = CH – CH2 OH & CH2 = CH – OCH3
O
O
7. &
.J
O
8. CH2 — CH — CH2 OH & CH3 — C — OCH 3
O
N
9. &
10. &
11. &
12. CH3OCH3 & CH3OCH2CH3
5
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Compounds Relationship
13. &
14. &
O CHO
SH
HS OH
15. &
OH
H CH3
IR
16. &
Et H H H
CH3 Et
OH
.S
OH
17. &
OCH3
18. OCH3 &
CH3 CH2CH3
H Br H Br
.J
19. &
H Cl H Cl
CH2CH3 CH3
CH3 Me
20. & Cl H
N
H Cl
Me CH3
21. &
N
22. & N
H
6
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Q.1 Which of following is 2° alcohol ?
OH
(A) (B) (C) OH (D)
OH OH
Q.2 Which of following is 3° alcohol ?

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

OH
OH
IR
Q.3 Which of following is 2° amine ?
NH2
NH2 NH–CH3
(A) (B) (C) (D)
N
CH3
.S
Q.4 Which of following compound has presence of 1°, 2°, 3°, 4° carbon ?
(A) (B) (C) (D)

.J
Q.5 How many ether is/are possible for molecular formula C4H10O.
(A) 1 (B) 2 (C) 3 (D) 4
Q.6 How many ketone is/are possible for molecular formula C4H8O
N
(A) 1 (B) 2 (C) 3 (D) 4
Q.7 How many alcohol is/are possible for Molecular farmula C4H10O (only structural)
(A) 2 (B) 3 (C) 4 (D) 5
O
Q.8 O–H
O
Number of Functional group in above compound is
(A) 3 (B) 4 (C) 5 (D) 6
7
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Q.9 The functional groups in Cortisone are:
HOH2C
CH3 OCH3
O
O Cortisoe
(A) Ether, alkene, alcohol (B) Alcohol, ketone, alkene, ether
(C) Alcohol, ketone, amine (D) Ether, amine ketone
O
O
O–H
Q.10 H SH
OH OH
How mnay types of functional groups are presention given compound.
(A) 6 (B) 5 (C) 4 (D) 7
IR
Q.11 The hybridization of carbon atom in the given compound
(A) sp2, sp (B) sp3, sp2 (C) sp3, sp (D) only sp2
.S
Q.12 Bond X is made by the overlap of which type of hybridized orbitals?
X
(A) sp and sp3 (B) sp and sp2 (C) sp2 and sp3 (D) none of these
.J
Q.13 The number of sp2 – sp2 sigma bonds in the compound given below is:
(A) 1 (B) 3 (C) 4 (D) 5

N
Q.14 Present functional group is

CH3 O
O CH3
(A) ketone (B) ester (C) ether (D) alcohol
Q.15 Present functional group is/are

O O
OCCH3
O
(A) ketone (B) ester (C) ether (D) A and B both
8
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Q.16 Find out the degree of carbon in the following compounds
CH3
(a) CH3 — CH2 — CH2 — CH2 CH2 — CH3 (b)
CH3 — CH2 — CH — CH — CH3

4-ethyl-3-methyloctane
CH3 CH3
1,2,7-trimethylcyclopentadecane
CH3
CH3
(c) (d)
CH3
CH3 CH3
1,1,2,5-tetramethylcyclopentane
Q.17 Calculate DBE value of C4H8 and draw possible structural isomer
IR
Q.18 Calculate C3H6O, DBE value & draw all possible structural isomer.
Q.19 Calculate DBE value of C5H10 & draw all possible structural isomer.
Q.20 Calculate DBE value of C4H6 and draw all the possible structural isomers.
Q.21 Calculate DBE value of C2H4O2 and draw all the possible structural isomers.
.S
.J
N
9
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Q.1 Identify relationship between following molecules.
(a) & (b) &
(c) & (d) &
(e) CH3 — CH2 — CH2 — CN & CH3 — CH — CH3

|
CN
(f) & (g) &
IR
(h) CH3 — CH — CH2 — CH3 & CH3 — CH2 — CH2 — CH2 — OH
|
OH
NH2
(i) & (j) &

.S
NH2
(k) &
Q.2 Calculate I.H.D. in the following molecules:–

CH—NH
.J
O 2 2
(a) (b) (c)
CH3
N
CH3 O O O
(d) Cl (e) H2N OH
O
Q.3 Calculate No. of  & / bonds in the following molecules:–
(a) (b) (c)
O = C—OH
Cl
(d) (e) N C — C  N
O
CN
10
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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 C1 C2 bond in the
following structure?
CH3
CH3CHCH2CH3
1 2 3 4
H CH3 H
CH3 CH2CH3 CH3 CH2CH3 CH3 CH3
(I) (II) (III)
H H CH3 H H H
IR
H H H
H H
C2H5 H H
(IV) (V)
H H CH3 H H CH3
H
.S
(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
C1–C2 bond of 1-iodo-2-methyl propane?
CH3 CH3 CH3 H
H CH3 I H I I CH3
H
(A) (B) (C) (D)
H H H H H CH3 H H
.J
I CH3 H CH3
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
N
Q.7 Which of the following best explains the reason for the relative stabilities of the conformers shown?
CH3 CH3
H H H CH3
(I) (II)
H H H H
CH3 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.
11
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Q.9 Draw the Newman structure for the most stable conformation of 1-bromopropane considering
rotation about the C1–C2 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
(ClCH2CH2Cl)
(b) The measured dipole moment of ClCH2CH2Cl 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.
CH3
H CH3
Q.12 ; If front carbon is rotated by 180° the conformation formed is:–
H H
H
IR
(A) gauche (B) anti (C) partially eclipsed (D) perfectly eclipsed
CH3
H CH3
Q.13 In the given energy diagram for butane the above conformation is represented at
H H
H
.S
which point
D B
E
A
C
angle of rotation
(A) A (B) B (C) C (D) D
.J
Q.14 If  for 1,2-dibromoethane is 0.75 D and Xanti = 0.7 Calculate  for gauche.
Q.15 Compare relative stabilities of given conformers.

CH3 CH3 CH3
H
N
H H CH3 CH3 H
(a) (b) (c)
H H H H H H
CH3 H H
Q.16 Draw most stable conformer of

(a) 3-methyl pentane
(b) 3-methyl hexane
Q.17 Draw most stable forms of

Z — CH2 — CH2 — OH
O O
|| ||
Z = OH, F, Cl, NH2, OMe, — C — OH, — C — H
12
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O
 ||
Q.18 (Me3) N — CH2 — CH2 — O — C — CH3; Most stable form of the compound.
 
Q.19 Draw most stable conformers of CH3 — CH2 — NH2 & CH3 — CH — O — H
|
CH3
Q.20 What is the effect on dipole moment of 1,2 – dichloroethane when the temperature is increased?
CH2 — COOH
Q.21 Most stable conformer of | (succinic acid)
CH2 — COOH
(a) at very low pH (b) at very high pH.
Q.22 Draw more stable conformation for the following–
   
(a)CH3 — CH — CH2 — CH3 (b) CH3 — CH — CH — CH3
| | |
CH3 CH3 CH3
 
(c)
IR
CH3 H
— CH — CH —
(d) (e) — C—— C — CH3
CH 3 CH 3
H CH3
Q.22 Compare Rotational barrier.
.S
     
(a) CH3 — CH2 — CH2 — CH3 CH3 — CH2 — CH3 CH3 — CH3
(i) (ii) (iii)
(b) — CH2— CH2 — — CH2— CH2 —
(i) (ii)
.J
— CH—2 CH —2
 
(iii)
(c) Cl Cl Br Br I I F F
CH2— CH2 CH2— CH2 CH2— CH2 CH2— CH2
N
          

(1) (2) (3) (4)
(d)
(i) (ii) (iii)

(e)
(i) (ii)
13
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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?
Br
(I) H (II) (III) (IV)

Br H
IR
Br
H H Br
Br
(V)
H
(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?
.S
(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
.J
Q.5 The Keq for the interconversion for the two chair forms of methylcyclohexane at 25°C 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
N
(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
14
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Q.8 What can be said about the magnitude of the equilibrium constant K for the following process?
H H
CH(CH3)2 CH3
H H
CH3 CH(CH3)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 () 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.
IR
Q.9 Most stable conformer of given compound is
HO—CH2—CH2—F
F F OH
HH H
H H H OH H H H
(A) (B) (C) (D)
H H HO
H H H F F
.S
OH H H
Q.10 Most Stable conformer of
.J
(A) (B) (C) (D)
Q.11 Which of the following pairs of structures represent conformational isomers?

CH3 CH3
N
H H H CH3
(A) (B)
H H H H
CH3 H
H
H
Br H H H H
(C) (D) H
Cl Br
Cl H H
H
H H
15
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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 C2 and C3.
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.
Me Me Me
H H Et
H H
(Pr = propyl)
H
Pr Me Pr Me Pr Me
Et
IR
Et H
(A) (B) (C)
.S
H Me H
Me Et Me
Et
Et H
Pr Me Pr Me Pr Me
H H
H
(D) (E) (F)
.J
+1 +1 +1 +1 +1
Anti All Gauche All eclipsed Highest in Lowest in

energy energy
N
Q.15 The equilibrium constant for the ring-flip of fluorocyclohexane is 1.5 at 25°C. Calculate the
percentage of the axial conformer at the temperature.
Q.16 Following eclipsed form of propane is repeated after rotation of

CH3
H
H H
H H
(A) 45° (B) 90° (C) 120° (D) 180°
16
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Q.1 Column I ColumnII

CH3
(A) H (P) cis-form
CH3
CH3
(B) (Q) trans-form
CH3
CH3
(C) (R) Keq is greater than one or equal to one when compound
CH3
undergo flip.
CH3
IR
(D) (S) Keq is less than one when compound undergo flip.
CH3
Q.2 Write correct order of stability of different form of following compound X with suitable reason.
Me
.S
CMe3
Me Me
Me
(I) (II) (III) (IV)
Me3C
.J
CMe3 CMe3
Me
Me3C
Et
N
CH3
Q.3 Identify most stable form of given compound
CH3 Et Et
Et
(A) (B) (C) (D)
Et CH3 CH3
CH3
Q.4 Dipole moment of a compound W – CH2 – CH2 – 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.
17
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Q.5 Compare stability:
OH
OH HO
(a) HO and
OH
(b) HO and
OH
HO
(c) and
IR
(d) and
(e) and
.S
(f) and
.J
(g) and
N
(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.
18
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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:–
R
IR
H
Keq
R Keq
.S
–H 1
– CH3 18
– CH2 — CH3 23
CH3
– CH 38
CH3
3800
.J
N
19
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Identify E/Z configuration:-
Q.1
HOCH2 CH2Cl
(1) C=C Me (2) C=C
N C CH3
CH3
F Cl
(3) H (4) C=C
C I Br
Me
O O
HO—CH2
O O
(5) C=C (6) C=C
IR
O N C O
O O
O
HO—C CH2O—Cl HOCH2 CN

(7) C=C (8) C=C
.S
HOH2C COCl OHC CH2 — OH
CH3 CH3
Me CH2 = CH C C—H
(9) C=C (10) C=C CH3 CH3
CH2 — CH C CH
Me Me
Me
CH C C—H F H
.J
(11) Me C=C (12) C=C

OH — CH2 C N Cl D
H
I CH2 CH2—C—I Cl — CH2 — CH2 CH2 — CH3
N
C=C H C=C
(13) (14)
Cl2 CH CH2—Cl HO — CH2 — CH2 CH — CD3
D
HS OH
(15) C=C (16)
CH3 — CH2 CH3 H
Br Cl
(17) (18)
H H
Me Et
CH3 CH3 CH3 H
(19) C=C (20) C=C
H H H CH3
20
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H H H
(21) (22) H (23) H

H
O
(24) (25)
H CH2—CH2—Br
(26) (27)
Br CH2—CH2—Cl
IR
H O Br OCH3
(28) (29)
Cl H CH3
O
Q.2
.S
1. Which of the following will show G.I. in acidic medium
(A) O (B) O (C) O
H
(D) C=O (E) O (F) O
H
.J
2. Which of the following will show G.I.

O O
|| ||
(A) CH3 – CH2 – C – NH2 (B) CH3 – C – NH – CH3
O O
|| Me
(C) C – NH – CH3 (D) C–N –
N
Me
3. Write cis/trans in the following of it show G.I.
(A) CH3 (B) (C)

CH3 Cl Cl
Cl Cl
C
21
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(D) (E) (F) (G)
Cl Cl Cl
(H) (I)
Cl
(J) Cl (K) Cl (L) Cl

Cl Cl Cl
IR
4. Following will show G.I.
(A) (B) (C) (D)

.S
C C C C
H CH3 H H H H H CH3
.J
N
22
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Calculate of geometrical isomer:
Case I  If both the ends are different
2n when n is number of stereogenic area or  bond which can show G.I.
Case II  If both the ends are same
2n–1 + 2p–1
If n = even ; P = n/2
n 1
If n = odd ; P=
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).
IR
(1) (2)
(3) (4)
(5) (6)
.S
(7) (8)
(9) (10)
H
H
(11) Me Me (12)
.J
H H
H H
Me Me
(13) (14)
H H Me Me
Me
N
(15) (16)
Me
(17) (18)
(19) CH3–CH=CH–CH=CH–CH=CH–CH3 (20) CH2=HC CH=CH–Me
(21) Me–CH=C=CH–CH2–CH=C=C=CH–Me (22)
23
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(23) Br–CH=C=C=CH–CH=CH–Br (24)
CH3 H
(25) (26)
H CH=C=CH2
(27) CH3—CH=CH CH=CH—CH3 (28) CH3–CH=C=C=CH–CH=CH–CH3
(29) (30)
CH3
(31) (32) CH3 – CH = CH – CH = N – OH
H
O
IR
(33)
O
Q.2 & are -------------------------

.S
Q.3 & are ---------------------
Q.4 Calculate total no. of geometrical isomers for the following:–
(A) (B) CH3 – CH = CH – CH = C= CH – CH3

(C) CH3 – CH = C = C = CH – CH3 (D) CH3–CH=CH–CH=C=CH–CH=C=C=CH–CH3
(E)
.J
CH3
Q.5 C=N Correct name of above compound is
Et OH
(A) syn – methylethyl ketoxime
(B) anti – methylethyl ketoxime
(C) syn – ethylmethyl ketoxime
(D) syn – methylethyl ketoxime
N
Q.6 is
C
H Cl
(A) E (B) Z (C) none (D) can‘t predict
24
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CH3 CH3 CH3 H
Q.1 C=C=C C = C = C
H l1 H l1 CH3
H
(I) (II)
I and II are not geometrical isomers of each other because
(A) I1 = I2 (B) I1 > I2 (C) I2 > I1 (D) they are geometrical isomers
CH3 l1 CH3 CH3 l2 H

Q.2 C=C=C=C C=C=C=C
H H H CH3
(I) (II)
I and II are not geometrical isomers of each other because
(A) I1 = I2 (B) I1 > I2 (C) I2 > I1 (D) they are geometrical isomers
IR
Q.3 MeCH = CH — CH = C = CH — CH = CH2
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) CH3 — CH = CH — CH = N — OH (B) (C)

.S
CH=CH–CH3
(D) CH3 — (CH = CH)3 — Ph (E) (F)CH3—CC—CH=CH—CH3
H
Q.5 Which of the following compound can show geometrical isomerism.

Br Cl CH3
(A) C=C (B) C
.J
I Cl CH3
F Et CH3 CH3
(C) C=C (D) C
CH3 CH3
Cl Et
Q.6 The geometrical isomerism is shown by

N
CH2 CH2 CHCl

(A) (B) (C) (D)
CHCl
Q.7 Which of the following double bond will not exhibit geometrical isomerism.
Me Ph Me
(A) C = C (B) C=O
CH3 C6H5 Ph
Me
(C) C = N — Me (D) Me — N = N — Me
Ph
25
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Q.8 Which of the compound show geometrical isomerism.
CH — Br H H
N N CH3 N
(A) (B) (C) (D)
Br CH3 O
O
Cl H Cl Me C–OEt
N N
(E) Me (F) Me (G) N-H
EtO–C
N
O Me
COOMe OMe
Me
NC COOMe N
(H) N N (I) (J) H2C = CH – C OCH2Ph
N
O H Me
N
H
IR
CH=CH–COOH
(CH3)3C (CH3)3C
C=C=C=C
(K) (L)
Cl Br
Cl Cl
.S
O
(M) (N)
O
Cl
Q.9
.J
Cl
The above conformation is
(A) cis (B) trans (C) will not show G.I. (D) can‘t predict
Q.10 for the boiling point of given compounds:–

N
H H H Cl
C=C C=C
CH3 Cl CH3 H
1 2
(A) 1 > 2 (B) 1 < 2 (C) 1 = 2 (D) none
Q.11 For the melting point of given compounds

Et CH3 H CH3
C=C C=C
H H Et H
1 2
(A) 1 > 2 (B) 1 < 2 (C) 1 = 2 (D) none
26
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Q.12 For which of the following keq > 1?
(A)
(B)
(C)
(D)
IR
.S
.J
N
27
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DPP-10 Time: 20 Minutes
Q.1 Compound P.O.S. C.O.S. Optically active
1.
CH3 CH3
H H
2.
H CH3
CH3 H
IR
3. H
H
CH3
CH3
.S
H H
4.
CH3 CH3
5. H H
.J
Cl Cl
6. Cl H
H Cl
N
7. Br
Cl H
Cl
H Cl
H
8. H
Cl
H
Cl
Cl
28
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9. H H
C=C=C
Cl Cl
10. H Cl
C=C=C
Cl Br
11. H H
C=C=C=C
Cl Cl
12. H H
C C
Cl Cl
13. Cl H
C C
H Cl
IR
14. H H
Cl Cl
15. H
.S
CH 3
CH3
16. Cl H
H Cl
.J
17.
C
H Cl
N
CH3 CH3
18.
C
H H
29
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CH3 CH3
19.
C
H Cl
20.
21.
IR
22. Cl I
I Cl
.S
23.
24. O = C = O
25. H
O=C=O
.J
H H
26. O=C=O
27.
N
N=N=N
H H
H
28. C No. of POS _ _ _ _ _ _ _ _
H H
H
H
29. C No. of POS _ _ _ _ _ _ _ _
Cl H
H
30
----------------------------------------------------------------------------------------------------
H H
C=C
30. No. of POS _ _ _ _ _
CH 3 CH 3
CH 3
H
C=C
31. No. of POS _ _ _ _
H CH 3
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) CH3 – CH = CH CH2 – CH3 (P) 8
IR
CH=CH–CH 3
(B) CH3 – CH = C (Q) 6
CH=CH–CH 3
(C) CH3 – CH = CH CH = CH – CH3 (R) 4
(D) Cl – CH = CH – CH = CH – CH = CH – CH3 (S) 2

.S
H5 C2 Cl H5 C2 Cl
Q.3 Statement 1: C=C and C=C are structural
CH3 Br Br CH3
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.
.J
(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? H

CH3 Cl Cl
N O
N–H CH3
N
(A) (B) C=C=C (C) (D)

H3 C
O N
H H
H
Q.5 Find out the correct option(s) ?

NH
CH3 CH3 CH3
(A) C=C Orientation is E (B) Orientation is Z
NH H H
H
31
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D
C=C
CH3
(C) H Orientation is Z (D) geometrical isomers are not possible
CH3
Q.6 Calculate total number of geometrical isomers in following compounds. (Excluding mirror image)
(i) CH3 – CH = CH – CH = CH – CH = CH – CH3
(ii) CH2 = HC CH = CH – Me
(iii) Me – CH = C = CH – CH2 – CH = C = C = CH – Me
Me
(iv) (v)
D
(vi) Br – CH = C = C = CH – CH = CH – Br
IR
.S
.J
N
32
----------------------------------------------------------------------------------------------------
Date: DPP- 11 Time: 15
minutes
Q.1 How many chiral carbon atoms are present in the following compounds?
H O H O
N PhOCH2 – C – NH S
(i) (ii)
CH3 N
H O COOH
Coccinellin Penicillin V
COOH
(iii) (iv)
IR
HO
Estrone Betulinic acid
Q.2 Assign priority number to the following groups as per Cahn, Ingold, Prelog sequence rule
(a) – CH2OH, –CH3, –CH2CH2OH, –H
(b) – Cl, –Br, –CH = CH2, –CH3
.S
O
(c) – C – H , –OH, – CH3, – CH2OH
(d) – CH(CH3)2, –CH2CH2Br, –Cl, –CH2CH2CH2Br
(e) – CH = CH2, – CH2CH3, , – CH3
CH3 CH3
.J
(f) – CH = CH2, – C  CH, – CH – CH2 – C – CH

CH3 CH3 CH3 CH3
(g) – CH2CH2CH2I – CH – CH – CH3 – CH – CH2CH3 –F
Br Cl
N
Q.3 Indicate whether each of the following structure has the R configuration or the S-configuration.
CH(CH3)2 CH2 – Br Br CH2 – Br D

(a) C CH2CH3 (b) C (c) C (d) C (e) C
CH2CH2Cl H OH CH3
CH3 CH2 – Br CH3CH2 OH Cl H CH3CH2 H
F CH3
Br Cl H CH =CH2 SH
(f) C (g) CH3 CH2CH3 (h) CH3CH2 F (i) F OH (j) H NH2
H
CH3CH2 CH3 Me
H Cl CH3
33
----------------------------------------------------------------------------------------------------
CH2 – Br
H NH2
CH3 CH2CH3 CHO CH3
CH2
(k) H Cl (l) (m) CH3 CH2I (n) H OH (o) H COOH
CH2 – CH3 H CH2 – OH CH2 – CH3
CH3 CH3 CH3 CH2CH3

CH2 – OH
HO H Br H H Br CH3 H
(p) HO CH3 (q) H Cl (r) H Br (s) H Br (t) Br CH3
CH2CH3 CH2CH3 CH2CH3 CH2CH3
CH2CH2CH2OH
COOH
H OH
(u) H OH
COOH
Q.4 Indicate whether each of the following structure has the R configuration or the S-configuration.
CH2 – Cl CH2 – OH
IR
CH = CH2 F
(a) C CH3 (b) C CH2CH2Cl (c) C CH3 (d) C OCH3 (e)
H CH3 OH D
COOH SH NH2 T
CH3
C OCH3
CH3O 18
H
.S
I SO3H NH2 CH3 CH2CH3 SR
(f) C D (g) DCH2 SCH3 (h) CH2 CH2OH (i) (j) H NR2 (k)
HS
NH2 CH3
CH3 CH2F Et
CH2OH
CH2CH3 CH3 OPh CH3 COOH Me
CH3 I (l) (m) D CH2Cl (n) H OH (o) D CHO
CH2CH2CH3 H CH3 Et
.J
CH2NH2 Me CH3 CH2Cl CH2CH3

(p) H2N CH2CH3 (q) H2N D (r) I Et (s) H OMe (t) CH3 H
D Br CH3 I H Br I H
CH2CH2CH2NH2 CH2CH2CH3 CH2CH2CH3 CH2CH3 CH2CH3
N
2 2 2 2
SO3H CH2CH2CH2COOH Et CH2CH2CH3

H Cl CH3 H Me D Cl H
(u) H (v) H (w) HO D (x) Br H
Cl CH3
SO3H CH2CH3 CH2CH2CH3
COOH
H OH
H OH H
(y) (z) CH3
H OH
CH2OH
34
----------------------------------------------------------------------------------------------------
Q.1 Column-I Column-II
Cl O
(A) Me (P) Total number of stereo isomers are odd.
Me Cl
Br
(B) (Q) Total number of stereocenter are even or have
Br
centre
H Cl
C
(C) (R) Compounds having plane of symmetry or axis of
C
IR
Cl H
symmetry
COOH
H OH
(D) (S) Compounds have zero dipole in given form.
HO H
COOH
.S
H Me
(A) Plane of symmetry (P) C C
Me H
Me Me
.J
(B) Centre of symmetry (Q)
Me
N
H
(C) Meso Compound (R) C
Me
Ph COOH
OOH
(D) Chiral atom is / are present (S) C H Ph H
H H
Cl H
(T) C=C=C=C
H Cl
Comprehension (Q.3 to Q.5)
35
----------------------------------------------------------------------------------------------------
On the basis of the following set of compounds, answer the following questions.
CHO H CH2 OH CHO CHO
HO H HOH 2C OH H OH H OH HO H
H OH HO H HO H HO H HO H
(I) H OH (II) H (III) H
HO OH (IV) HO H (V) HO H
HO H HO H H OH H CH2 OH HO H
CH2OH CHO CHO OH CH2 OH
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:
IR
CH3 CH3 CH3 CH3 H CH3 CH3 H
H H H H CH3 H H H3 C
H CH3 H3 C H H CH3 H3 C H
A B C D s
.S
Q.7 Which of the following compounds should have the larger energy barrier to rotation about the
indicated bond ?
(a) Me3C  CMe (b) Me3Si SiMe3

Q.8 How many compounds are theoretically possible for formula C3H6O (excluding stereoisomers)?
Q.9 How many acyclic isomers of C5H10 are possible which are incapable of showing Optical
.J
Isomerism?
Q.10 How many stereoisomers are possible for the following?

Me CH=CH–CH=CH 2
N
Me CH=C=C=CH–Me
(A) 16 (B) 4 (C) 6 (D) 8
Paragraph for question nos. 11 to 13

Answer the following questions based on given reaction
Cl2
hv
Products.
(monochlorination)
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
36
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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 (C6H6)?
(b) How many chiral centres are present in the following compound?
O
Ph
S
O
Br
(c) Minimum carbon atoms required for an alkane to show optical isomerism.
IR
.S
.J
N
37
----------------------------------------------------------------------------------------------------
Date: DPP NO- 13 Time: 15
minutes
H CO2 H
OH
(A) (P) chiral
OH
CO2 H H
CO2 H H
OH
(B) (Q) achiral
OH
OH CO2 H
H
CO2 CH2 CH2 OH
(C) (R) meso
IR
CO2 H
H
H H
CO2 CH2 CH2 O2 C
(D) (S) compounds containing even number of chiral
CO2 CH2 CH2 O2 C
.S
H H
center

Cl Cl Cl Cl
(A) and are (P) Structural isomers

.J
H Me Me H
CH3 CH3 CH3 H
(B) and are (Q) Compounds are optical
H H H CH3
N
isomers and enantiomers

Me H
Me H C
C C
(C) and Et are (R) Compounds which are
C O CH3 geometrical isomer and
C
H CH2–CH2–COOH diastereo isomers
O
COOH COOH
(D) H OH and HO H are (S) Compounds are
H OH HO H
COOEt COOEt
geometrical
isomers and enantiomers
(T) Not isomers
38
----------------------------------------------------------------------------------------------------
F F
Q.3 Statement 1:
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
IR
Q.5 The correct stability order of the following species is
H H Me
Me H Me
Me
H Me
H H Me
.S
(a) (b) (c)
(A) c < a < b (B) c = b < a (C) c < a = b (D) a = b = c
Me
Q.6 This compound shows:
Et
(A) geometrical isomerism (B) optical isomerism
(C) both (D) none
.J
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°
N
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
39
----------------------------------------------------------------------------------------------------
Q.11 Select resolvable compounds.
HO
(A) (B) Cl
O
N
OH
CH3 O
H
H
H Me O
(C) (D) O N–H
CH3 O
H
Q.12 Calculate total number of stereocentre, prochiral carbon and theoretical stereoisomer in the
following compound.
IR
N
S
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
.S
4434.
Q.13 How many geometrical isomers are possible for the following structure.
H
Q.14 Relationship between molecules:–
CH3 CH3 CH3 CH3
.J
(a) &
C C
H H H H
N
H H Cl H
(b) C=C=C=C & C=C=C=C
Cl Cl H Cl
CH3 CH3 CH3 CH3
(c) &
Cl Cl
(d) CH3 & CH3
CH3 CH3
40
----------------------------------------------------------------------------------------------------
(e) &
(f) &
Q.15 Calculate total no. of optical isomers, optically, active, meso & enantiomer pairs corresponding to
the following:–
(a)
IR
.S
.J
N
41
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DPP-14 Time: 15 minutes
Q.1 Match the following :

Column I Column II
O
Me C – Me
(A) (P) Meso compound
Me Progesteron
O
Me2N
Me OH
C  C – Me
(B) (Q) Compound having even no. of chiral carbon
IR
(RO–486/mifepristone)
O
H
(C) O (R) Optically active compound
H
O N
H
COOH
.S
H OH
(D) (S) Compound having odd no. of chiral carbon
H OH
COOH
(T) Compound having odd no. of prochiral carbon.

Column I Column II
Et N
(A) Compound having only plane symmetry and (P) N
.J
N
Et
Et
axis of symmetry (Consider the given chair form
only)
Me Me
N
(B) Compound having center of symmetry, plane of (Q)
symmetry and axis of symmetry
(C) Compound having axis of symmetry (C3) (R)

N
:
(D) Compound having C2 axis of symmetry but absence (S) 2,2,3,3-Tetramethyl butane in
of plane of symmetry staggered conformer
42
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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.
Et
Q.4 Assertion : Et is most stable of conformer of
Me Me Me
Me
Reason : Torsional strain and flag pole interactions cause the boat conformation to have
considerably higher energy than the chair conformation.
IR
Q.5 Correct statement about D-mannitol (in given form) :
OH OH
HO
OH
OH OH
(A) C3 axis of symmetry (B) C2 axis of symmetry
.S
(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.
D H Me Me Cl
O O O O
(A) H O–C Me and D O–C OH (B) and
Cl Cl
Me OH H H Cl
.J
COOH COOH Me Me
Me
H OH HO H
(C) HO H and HO H (D) and
COOH COOH Me
Q.7 An unknow compound weighing 4.5 gm is dissolved in enough carbon tetrachloride to make a total
N
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 :
F
Br I Cl
F C=C=C
(a) (b) (c)
Cl
Br Cl
H
CHO NO2 SO3H H H
H OH CH3
(d) (e) (f)
H OH
CO2H SO3H NO2 CH3 CH3
43
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Me CH3 CH3
H
Et H CH3 CH3 CO2H
(g) (h) C=C (i) N–N
Cl H H HO2C
H
Me H CH3 CH3
H3C CH3
HO2C CO2H C H
N  H H C
N H C
N
(j) H5C6 C6H5 (k) C6H5 (l) O C
H5C2O2C
HO2C CO2H C
H CH3
C=C=C=C
(m)
IR
NO2 NO2
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
.S
following molecule. Also draw the structures of pair of distereomers.
H
N H
N O
COOH
.J
Q.10 Select chiral molecule out of the following list compound.

H
CH3 HOOC O
OH
HO H C=C=C C
(i) (ii) (iii) (iv) N C6H5
HO H H
O N
COOH HO2C
N
CO2H CH3 CH3 Cl

N=N
(v) HO2C (vi) (vii)
(Azodiformic acid) CH3 CH3
CH3 CH3
(viii) (ix)
CH3 CH3 CH3 CH3
44
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DPP-15 Time: 15 minutes
Column I Column II
H
(A) H C (P) It can show geometrical isomerism
Cl
(B) H H (Q) Optically active compound

C
CH3 CH3
O O
(C) (R) Presence of odd, number of chiral carbon
NH NH
Br Br
H
IR
(D) C=C—C–C=C (S) Resolvable compound
H HH H Br
(T) Presence of Pseudo chiral centre

Column I Column II
OH OH
.S
(A) H (P) Total number of stereoisomers is odd for the structure
CH3
O
H
H CH3
(B) (Q) Total number of stereoisomers is even for the structure
CH3 – C
CH2
CO2H
.J
H OH
(C) H OH (R) Odd number of chiral centre
CO2H
OH
H
HO
(D) CH2NH2 (S) Even number of chiral centre
N
HO
(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.
45
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CH3 O
Q.3 Assertion : is an optically active compound.
Cl CH3
Cl
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 ?
F Br
F HO
H
H3C
Cl CH3
F F F F
H3C H H3 C H H CH3 H3C H
(A) F Br (B) Br F (C) F Br (D) F Br
Cl CH3 H3C Cl H3C Cl H3C Cl
IR
OH OH OH OH
Q.6 How many plane of symmetry are present in following compound.
(A) 2 (B) 1 (C) 0 (D) 3

.S
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 -pinene has a specific rotation D20 = + 50°. A sample of -pinene containing
both the enantiomers was found to have a specific rotation value D20 = 30°. The percentage
.J
of the (+) and (–) enantiomers present in the sample are, respectively.
Q.8 Consider the following six structures :

OH OH
H H
N N
(I) O (II) O
N
HO CH3 CH3 HO CH3 CH3
OH OH
H H
N N
(III) O (IV) O
OH OH
H H
N N
(V) O (VI) O
46
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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

Br I NO2 SO3H
(i) (ii)
I Br SO3H NO2
N Me
(iii) Ph – S = O (iv)
CH3 Me N
.. Br
N
(v) MeCHBrCH2Me (vi) Me
IR
Me
..
N
(vii) (viii)
Me O
H Me Cl
Me N
.S

(ix) MeN DH2Br (x) MeCH2CHCH2Me
OH
SO3H NO2
Cl
(xi) (xii) C = C = CH2
H
SO3H NO2
.J
N
47
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Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
(1)
(a) (b)
OH OH OH
(2)
IR
OH OH OH
(a) (b) (c)
(3)
CO2H CO2H
.S
(a) (b)
H Me H H
(4)
Me H Me Me
(a) (b)
HH
.J
(5)
(a) (b)
Me Et
H OH HO H
N
H OH HO H
(6) Et Me
(a) (b)
Cl Cl Cl Cl
(7)
Br Br Br Br
(a) (b)
(8)
48
----------------------------------------------------------------------------------------------------
(a) (b)

isomer
OH OH
(9)
(a) (b)
(10) OH OH
O O
(a) (b)
HO
H
(11) NH2
IR
HO COOH
(a)
OH
HOOC
OH
H NH2
(b)
.S
(12)
(a) (b)
Cl
.J
(13)
Cl
(a) (b)
O H Cl
(14)
N
H O
Cl
(a) (b)
(a) (b)
O Me
(15) S—O
O
(a)
Me
O
O—S
O
(b)
49
----------------------------------------------------------------------------------------------------
isomer
Cl
(1) Cl
(a) (b)
(2) N N
(a) (b)
IR
Me H Me H
O
(3) Me
H OH
O O
(a) (b)
.S
COOH COOH
(4) H OH HO H
H OH HO H
COOEt COOEt
(a) (b)
Cl Cl Cl Cl
.J
(5)
H Me Me H
(a) (b)
OH OH
N
(6)
H H
(a) (b)
H H
Me H
Br Br
(7)
H H H
(a) (b)
Me Et
(8) H OH HO H
H SH HS H
Et Me
50
----------------------------------------------------------------------------------------------------
(a) (b)

isomer
Cl Cl
Cl Cl
(9)
Cl Cl
(a) (b)
O OH
(10)
N N
H
IR
(a) (b)
(11)
.S
(a) (b)
H H
(12)
Me H
H Me
.J
(a) (b)
Br Cl
(13)
N
Cl Br
(a) (b)
(14) OH OH
HO H HO H
(a) (b)
H Cl H
Et
Cl H
(15) H Cl
Cl Et
(a) (b)
51
----------------------------------------------------------------------------------------------------
isomer
H2C = N CH = NH
O
(1)
O
(a)
H2C = N CH = NH
O
IR
(b)
O
(2) C OH
H Me
(a)
.S
Me
C H
OH
O
(b)
COOH H
.J
H Br Br COOH
(3) H CN H
HO
OH CN
(a) (b)
O O
N
(4)
Br Br
(a) (b)
Br Br Me
H
(5) H Br
H
Br H
(a) (b)
O OH
(6)
(a) (b)
52
----------------------------------------------------------------------------------------------------
isomer
CH3 CH3
H OH HO H
(7)
H OH H OH
CH3 CH3
(a) (b)
CH3
H OH
HO H
CH3
(c)
IR
(8)
(a) (b)
CO2H CO2H
H OH HO H
.S
(9) H OH HO H
CO2H CO2H
(a) (b)
Et
(10) Me Me
.J
Et
(a)
Me Et
N
Et Me
(b)
O
(11)
O
(a)
O
O
(b)
53
----------------------------------------------------------------------------------------------------
isomer
N
(12) N
(a) (b)
N
(13) N
(a) (b)
Cl Br
I
IR
(14)
Br Cl
I
(a) (b)
O O
.S
(15)
O O
(a)
O
O
O
O
.J
(b)
O
O
O
O
N
(c)
NH Me NH2
(16)
(a) (b)
NH
NH2
(c) (d)
54
----------------------------------------------------------------------------------------------------
isomer
OH O
(1)
(a) (b)
OH
IR
(c)
H
N N
(2)
O OH
(a) (b)
.S
(3) OH O
(a) (b)
OH OH
(c) (d)
.J
(4)
(a) (b) (c)
Me
N
N N
(5)
OH
O
(a) (b)
(6) Me — C  N 
Me — N —
—C
(a) (b)
(7) OH
OH
(a) (b)
55
----------------------------------------------------------------------------------------------------
isomer
OH H
(8)
O OH O
(a) (b)
O
O H
(c)
O O
(9)
(a) (b)
IR
(10) CH3OH OH
(a) (b)
OH OH
(11)
.S
CH 3
(a) (b)
Cl Cl
Cl
(12)
.J
Cl
(a) (b)
(13) CN
CN
(a) (b)
N
(14) CO2H
CO2H
(a) (b)
(15)
(a) (b)
56
----------------------------------------------------------------------------------------------------
If there is presence of given symmetry then writes () otherwise (x)
Compound P.O.S(s) C2 C3 S4 S2
(1)
N
Cl
(2)
H H
IR
C
(3) C
C
H H
.S
(4)
.J
Br
CH3
(5) C
CH3
CH3
CH3
N
(6)
CH3
Br
Br Br
(7)
Br Br
Br
57
----------------------------------------------------------------------------------------------------
If there is presence of given symmetry then writes () otherwise (x)
Compound P.O.S(s) C2 C3 S4 S2
(1)
(2)
IR
(3)
(4)
Cl
.S
Cl
(5) C=C
H H
Cl H
(6) C=C
H Cl
H
.J
Br
(7) H
Br
CO2H
H OH
(8)
HO H
N
CO2H
(9)
(10)
58
----------------------------------------------------------------------------------------------------
1. Find (m) meso compounds & optically active (a) and total stereoisomer (a + m) of following
compounds
Compound Meso (m) Active isomer (a) (a + m)
H3C CH3
(1)
H3C CH3
Br
Cl
(2)
Cl
(3)
IR
N
H
(4)
Cl Cl
.S
Cl Br
H3C
(5) CH3
Cl Br
O OH
Cl
(6) Cl Cl
Cl
.J
O
HO
Cl
(7)
H3C CH3
N
O Cl
(8) H3C
CH3
H3C O
(9)
59
----------------------------------------------------------------------------------------------------
H3C
(10) CH3
CH3
Br
(11)
Br
IR
Br
(12)
Cl
H H
C
.S
(13)
H3C CH3
Cl Cl
(14)
Cl
Cl Cl Cl
.J
CH3
(15)
CH3
H 3C
H 3C
N
Br
H3C
(16)
HN
CH3
60
----------------------------------------------------------------------------------------------------
compounds
(1)
CH3
IR
(2) Cl
Cl
Cl
(3) CH3
CH3
Cl
.S
Cl
CH3
(4)
Br CH3
Br
Br Br
.J
(5)
Br
CH3 Cl SH
H3C CH3
(6)
N
Cl Br
(7) H3C
CH3
CH3
H3C
(8)
Cl
61
----------------------------------------------------------------------------------------------------
compounds
(1)
Br Cl
(2)
Cl Cl
IR
Cl
CH3
(3)
CH3
OH
HO3
CH3
.S
(4)
OH
H3C
(5) CH3
HO
Br
.J
Cl
(6)
CH3 CH3
N
(7)
Cl Cl
CH3 CH3
(8)
Cl Br
O OH
Cl Cl Cl
Cl
(9) Cl
Cl Cl Cl
HO O
62
----------------------------------------------------------------------------------------------------
compounds
(1)
Cl Cl
CH3
(2)
H3C Cl
Br
CH3
(3)
CH3
IR
CH
(4)
Cl CH
.S
(5)
CH2
(6)
CH2
.J
CH3
(7)
H3C
CH3 H3C
H3C
(8) CH3
N
CH3 H3C
Br
(9) H2C CH3
H3C CH3
(10)
HO
O OH
Cl Cl Cl
(11) Cl
Cl
Cl Cl Cl
HO O
63
----------------------------------------------------------------------------------------------------
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
N
(1) Et
Me
C
(2) Me
IR
(3)
H
HO COOH
.S
O
S
(4) Me
OH
.J
(5)
OH
OH
(6) H
N
H
OH
Cl
Cl
(7)
O OH
HO
(8)
HO OH
OH
64
----------------------------------------------------------------------------------------------------
molecule molecule inactive Chiral center
Me
Cl
H
(9) H
Cl Me
H
Me O
(10) O O
O
Me
H
CH2OH
Cl Cl
(11) H
IR
H
CH2OH
(12)
Me Me
.S
O
Cl
(13)
F Br
.J
(14)
Me
Cl H
(15)
N
H Cl
Me
Br
Me
H
(16)
Br
Me
H
65
----------------------------------------------------------------------------------------------------
Me
Me
(1)
Me
(2) Me
IR
H
NO2 COOH
(3)
NO2 F
.S
Cl Cl
(4)
F F
Me
.J
H Cl
(5) H Cl
H Cl
Me
N
(6) O=C=O
H Br
(7) C C
Br H
F NO2
(8) C=C=C=C
Cl Me
66
----------------------------------------------------------------------------------------------------
Me H
C=C=C=C
(9) H Me
H H
CO2CH2CH2O2C
(10)
CO2CH2CH2O2C
H H
CO2H H
H
(11)
OH
HO CO2H
IR
H
CO2CH2CH2OH
(12)
CO2H
H
H
.S
CO2H
OH
(13)
OH
CO2H H
Me H
O NH
(14)
HN O
.J
H Me
H Me
O NH
(15)
N
HN O
H Me
Cl Cl
H H
(16)
67
----------------------------------------------------------------------------------------------------
Ph COOH
(1) H H Ph
H
COOH H
H H
(2)
Me COOH
H
(3)
IR
COOH
Me H
F
Br
(4) F
Br
.S
I
(5) C=C=C
Cl
(6)
.J
Me Cl
(7)
N
Me
(8)
Me Me
(9)
Me Me
68
----------------------------------------------------------------------------------------------------
S.No. Compound Optically Chiral Achiral Optically No. of
active molecule molecule inactive Chiral center
(10) H H
Me Me
Cl
(11)
Cl
Me Cl
Me
Br
(12) COOH
Me Me
IR
Br Me Br OH Me Br
(13) Me Me
H Me OH Br Me H
D COOH
.S
(14)
Me H
.J
(15)
O
O
H N C6H5
N
N
(16)
HO2C
CH3
H Cl
(17)
Cl H
CH3
69
----------------------------------------------------------------------------------------------------

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IIT-JEE Chemistry by N.J.

Sir ORGANIC chemistry

(k) O — CH3 & CH2 — OH

(l) CH3 &

(m) & CH3 — C  C — CH3

(n) CH3 — CH2 — CH2 — CH2 — NH2 & CH 3— CH2 — N

Q.2 Fill in the blanks:–

(b) —O— & —O— are _ _ _ _ _ _ _

(c) H & H are _ _ _ _ _ _ _

(e) CH3 — CH2 — CH2 — C  N & CH3 — CH2 — CH2 — N 

Q.3 Column matching

6. CH2 = CH – CH2 OH & CH2 = CH – OCH3

12. CH3OCH3 & CH3OCH2CH3

Q.2 Which of following is 3° alcohol ?

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

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

(A) 1 (B) 2 (C) 3 (D) 4

(A) 1 (B) 3 (C) 4 (D) 5

Q.14 Present functional group is

Q.15 Present functional group is/are

CH3 — CH2 — CH — CH — CH3

(a) & (b) &

(c) & (d) &

(e) CH3 — CH2 — CH2 — CN & CH3 — CH — CH3

(f) & (g) &

(i) & (j) &

Q.2 Calculate I.H.D. in the following molecules:–

(a) (b) (c)

(a) (b) (c)

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

Q.15 Compare relative stabilities of given conformers.

Q.16 Draw most stable conformer of

Q.17 Draw most stable forms of

(b) — CH2— CH2 — — CH2— CH2 —

          

(i) (ii) (iii)

(A) C – O – C bond angle in cation. ………………………………………..

(I) H (II) (III) (IV)

(B) Both groups are axial

Q.7 Name the compound shown below.

(A) trans-1, 2-dichlorocyclohexane (B) cis-1, 2-dichlorocyclohexane

Paragraph for Question Nos. 9 to 11

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

Q.11 Which of the following pairs of structures represent conformational isomers?

(A) and (B) and

(C) and (D) C and C

Anti All Gauche All eclipsed Highest in Lowest in

Q.16 Following eclipsed form of propane is repeated after rotation of

Q.1 Column I ColumnII

Q.6 Draw 1,2,3,4,5,6-hexamethyle cyclohexane in which all

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

Q.9 Draw structure & compare stabilities of following

HO—C CH2O—Cl HOCH2 CN

(11) Me C=C (12) C=C

(21) (22) H (23) H

(A) O (B) O (C) O

2. Which of the following will show G.I.

(A) CH3 (B) (C)

(J) Cl (K) Cl (L) Cl

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

(19) CH3–CH=CH–CH=CH–CH=CH–CH3 (20) CH2=HC CH=CH–Me

(21) Me–CH=C=CH–CH2–CH=C=C=CH–Me (22)

(27) CH3—CH=CH CH=CH—CH3 (28) CH3–CH=C=C=CH–CH=CH–CH3