Isomerism Ans

IIT-JEE CHEMISTRY BY N.J.
SIR
ORGANIC CHEMISTRY
Answers for Isomeris DPP ( Conceptual Improvement of Isomerism )

Q.1(a)
(f)
(k)
(p)
Q.2(a)
(f)
Q.3
Identical
(b)
Position
(g)
Functional
(l)
Chain
(q)
Metamers
(b)
Functional
(g)
A-Q, B-Q, C-R, D-S
Position (c)
Chain
Functional
Ring chain
Identical
Functional
1.
5.
8.
11.
13.
17.
21.
Position isomers
Identical
Functional
Ring chain
Position isomers
Chain
Identical
2.
6.
9.
12.
14.
18.
22.
1.
8.
Q.15
C
B
D
2.
9.
D
B
Answers of DPP No. 1

Position (d)
Functional
(e)
Position
(h)
Position (i)
Position (j)
Functional
(m)
Functional
(n)
Functional
(o)
(r)
Chain
(c)
Metamers
(d)
Metamers
(e)
(h)
Metamers

Metamers
3.
Positional
Functional
7.
Functional
Non-identical
10.
Non-identical
Non-identical / homologous
Chain isomers
15.
Position
Position
19.
Position
20.
Functional
3.
10.

4.
B
5.
C
Q.11 D
Q.12 C
B
C
Q.16.
(a) (1,2,3) CH3 CH2 CH2 CH2
CH2 CH3 (b)
4-ethyl-3-methyloctane
(c) (1,2,3, 4)
(5) DBE = 1
2
3 3
A
C
C
C
7.
Q.14
CH3
(1,2,3)
CH3
CH
1 3
1
1,2,7-trimethylcyclopentadecane
1
4
2
(d) (1,2,3, 4)
2
2
2
3
CH3
1
1,1,2,5-tetramethylcyclopentane
Q.17
Metamers
CH3
3
1
CH3
4 CH3
16.
Identical
2
2
Chain
CH3 CH2 CH CH CH3
Functional
4.
6.
Q.13
2
Functional
CH2 = CH CH2 CH3,
CH3
1
CH3 HC = CH CH2,
CH3 C = CH2
CH3
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OH
O
Q.18
DBE = 1 (5)C3H6O
CH3 C CH3 ,
CH3 CH2C
H
Q.19
CH2 = CH O CH3
CH2 = CH CH2 OH,
(5) DBE = 1
CH3CH2CH2HC=CH2,
CH3CH2HC=CH CH3,
CH3 CH2 CH = CH2 ,

CH3
CH3CH=CCH3 ,
CH2=CHCHCH3 ,
CH3
Q.20
CH3 CH2 C CH, CH3 C C CH3,
(9) DBE = 2 C4H6

CH3 CH = C = CH2,
(4)
O
Q.21
CH3
C CH2 OH,
CH2=CH CH = CH2,
CH3 C
H C O CH3 ,
OH
OH

Q.1(a) Position
(b)
Position (c)
Position (d)
Position (e)
Chain
(f)
Position (g)
Position (h)
Position (i)
Position (j)
Chain
(k)
Position
Q.2(a) 7
(b) 3
(c) 4
(d) 2
(e) 4
Q.3 (a) = 2, = 30 (b) = 5 = 17 (c) = 3 = 34
(d) = 4 = 27 (e) = 4 =3
(f) = 2 = 5 (g) = s2 = 7
Et
Et
Q.4
Q.5
Q.6
Q.7
Q.8
H
CH3
CH3
CH3
Br
Q.9
CH3CH2CH2Br
H
Q.10
CH3 CH CH3
Cl
Q.11
Cl
(anti)
(b) 1, 2
H
C
Q.13
Q.15
a>c>b
H
H
Cl
H
(a) (gauche)
Q.12
CH3
CH3
CH3
Cl
Q.14
0.75 D = 0.3 X gauche
gauche =
7.5
= 2.5 D.
3
CH3
Et
H
Q.16
CH3CH2CHCH2CH3 (a)
CH3
C2H5
H
(b) CH3CH 2CHCH 2CH 2CH 3
CH3
CH3
CH3
C2H5
H

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+
N(Me)3
OH O
CH
Q.17
O
C
Q.20
Q.19
CH3
O
CH3
Q.21
N
H
CH3 CH3
CH3
Q.18
(a) gauche
(b) anti
Q.22
CH3
CH3
(a)
CH3
Et
H
CH3
(b)
(c)
CH3
CH3
CH3
CH3
CH3
Ph
Ph
CH3
CH3
(d)
(e)
CH3
CH3
CH3
Ph
Q.23
(a) i > ii > iii
(b) i > ii > iii
Q.1
Q.5
(a) 120 (b) < 10928

E
(c) 0
(c) 3 > 2 > 1 > 4 (d) i > ii > iii

(e) i > ii
(d) 60
Q.2
C
Q.3
B
Q.4
Keq = 18
x
100-x
100 x
= 18
x
Q.6
18 = 100 x
19 = 100
X = 100/19
C
Q.7
D
O
C
Q.8
H
O
Q.13
Q.14
Q.9
Q.10
+1
+1
+1
C/A
B/D/F
Anti
All Gauche All eclipsed
Q.11
A, B, D Q.12
+1
+1
Highest in
energy
Lowest in
energy
F
Q.15
F
x
Keq = 1.5
100-x
100 x
= 1.5
x
1.5 = 100 x
25 = 100
X=
Q.16
100
10
25
= 40%
C

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Q.1
Q.4
A P, R; B Q, S; C P, R; D Q, R
Xanti = 3/4

Q.2
(IV) > (III) > (I) > (II)
OH
Q.5
Q.3
OH HO
(a)
and
HO
OH
HO
(b)
and
OH
OH
(c)
and
(d)
and
(e)
and
(f)
and
(g)
and
(h)
and
Cl
Cl
Q.6
(a)
Cl
Q.8
c>d>b>a
Cl
Cl
Cl
Cl
(b) Cl
Cl
Cl
Q.9
(a)
(b)
Trans
Q.1
Q.7
Cl
Cl
Cis
Cis

(1) Z (2) Z (3) E (4) Z (5) Z
(6) E (7) E
(8) Z (9) Z (10) E (11) Z
(14) E (15) Z (16) E (17) E (18) E (19) Z (20) E (21) Z (22) E (23) E (24) Z
Trans
(12) Z (13) E

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Z
(25) Z
(26) Z
Q.2
(1) (A) X
(B) X
(C)
(D) X
(2) (A) X
(B)
(C)
(D) X
(3) (A) Cis

(H) Trans
(B) Trans
(I) Cis
(4) (A) X
(B) X
Q.2
Q.4
Q.5
Q.1
Q.6
Q.8
A
D
(A)
(N)
B
Q.9
(28) E
(E)
(C) Cis
(J) X
(C)
(F)
(D) Cis
(K) Trans
(F) Cis
(G) Trans

2
31
(31)/2
31
(31)/2
3
(6) 2
(7) 2 +2
=6
(8) 2 + 2
=6
(9) 2
1
1
1
1
1
1
4
(12) 2 (13) 2 (14) 2 (15) 2 (16) 2 (17) 2 (18) 2
1
2
1
3
(21) 2 (22) 2 (23) 2 = 4
(24) 2 (25) 2 (26) 2 (27) 2
1
(33) 2

2
3
1
1
Q.4
(A) 2 (B) 2 (C) 2 (D) 2 (E) 2 (F) 2
C
Q.3
(A), (B)
(C) X (D)
D
(E)
(F) X
(G)
Q.10
Q.12
(A) = Keq < 1
Q.11
(E) Trans
(L) Cis
(D)
Q.2
Q.7
(B)
Compound
(29) Z
(2) 2
(3) 2
(4) 2
(5) 2
(1) 2
21
2/21
1
(10) 2 + 2
=2+1=3
(11) 2
31
(31)/2
3
=6
(20) 2 = 8
(19) 2 +2
2
2
2
2
(28) 2 (29) 2 (30) 2 (31) 4 (32) 2
Trans Q.3
Trans
31
(31)/2
=6
(A) 2 + 2
1
(B) 2 = 2
1
(C) 2 = 2
2
(D) 2 = 4
1
(E) 2 = 2
B, C
Q.6
B
Q.1
(27) E
(H)
(I)
(J) X
(B) Keq = 1

P.O.S.
(K)
Q.5
A,B,C
(L)
(M)
(C) Keq > 1
(D) Keq = 1
C.O.S.
Optically active
1.
CH3
H
CH3

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2.
CH3
CH3
3.
H
CH3
CH3
H
H
4.
5.
CH3
CH3
H
Cl
Cl
6.
Cl
Cl
Br
7.
Cl
Cl
H
Cl
H
8.
Cl
H
H
Cl
Cl
9.
H
Cl
10. H
Cl
C=C=C
H
Cl
C=C=C
Cl
Br

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11. H
Cl
12.
H
Cl
13.
14.
C=C=C=C
Cl
H
Cl
Cl
H
C
C
H
Cl
H
Cl
H
Cl
15.
CH 3
CH3
H
H
Cl
16. Cl
17.
H
18.
C
Cl
CH3
CH3

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19.
CH3
CH3
Cl
20.
21.
Cl
22.
Cl
23.
24. O = C = O
25.
26.
O=C=O
H
O=C=O
27.
N=N=N
H
H
C
28.
No. of POS = 4C2 = 6

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H
C
29.
Cl
No. of POS = 3
H
C=C
CH3
No. of POS = 2
CH3
CH3
31.
H
30.
H
C=C
No. of POS = 1
CH3

Q.1
(i) 2 (ii) 3 (iii) 4 (iv) 10
Q.3
(d) 3 > 1 > 2 > 4

(a) R (b) R (c) S
(n) R (o) S (p) S
Q.4
(a) R (b) R
(n) T (o) S
(v) R, S
Q.2
(a) 1 > 3 > 2 > 4
(b) 2 > 1 > 3 > 4
(e) 3 > 1 > 2 > 4

(f) 4 > 2 > 3 > 1
(d) S (e) R (f) S (g) R (h) S (i) S
(q) R, R
(r) R, R
(s) S, R
(c) S (d) S (e) R

(p) S (q) R,R
(w) R, S
(f) S (g) R
(r) S,R
(x) R, S
(h) S (i) S
(s) S, R
(y) R, R, R
(c) 2 > 1 > 4 > 3
(g) 4 > 3 > 2 > 1

(j) S (k) S (l) R (m) S
(t) R, S
(u) R, S
(j) S (k) S
(t) R, S
(z) R
(l) R (m) S
(u) R, S

Q.1
Q.3
Q.6
Q.7
Q.14
A Q; B Q; C R,S; D Q;
Q.2
A T,P,S; B T, P; C S; D Q;
B
Q.4
Q.5
D
A-B = Enantiomer, C-D = Enantiomer, A-C, A-D = distereomers, B-C & B-D = disteromers
A
Q.8
8
Q.9
5
Q.10
Q.11 C
Q.12
Q.13
(a) 4 (b) 4 (c) 7
Q.1
Q.3
Q.10
Q.14
A S,P; B Q; C S,P; D S,R;

A
Q.4
C
Q.5
A
Q.6
Q.11 A, B, D
Q.12
(a) diastereomers
(b) distereomers
(e) enantiomers
(f) distereomers
No-sym. Present
(i)
optical isomers = 27 = 128.
(ii)
optically active = 2n = 27 = 128
(iii)
meso = 0
Q.15
(iv)
Q.1
enantiopair
A Q, R;
A T; B S,R; C P; D T;
Q.7
A
Q.8
C
Q.9
Q.13 4
(c) distereomers
(d) distereomers
Q.2
A
2n 128
=
= 64.
2
2
B S, R, T; C Q, R, T; D P, Q;

Contact: 9414969800, 9549908816
Q.2
Q.3
Q.7
Q.8
A P, R;
B
Q.4
= 125
(A) chiral
(H) achiral
B S;
D
Q.5
C P, R, S; D Q;
B
Q.6
(A) X (B) X (C)
(B) achiral
(I) chiral
(C) achiral
(J) chiral
H
N:
*
(a) 12.5
(b) + 8.6
(E) chiral
(L) chiral
(F) achiral
(M) achiral
(G) chiral
(v) achiral
(vi) achiral
(vii) chiral
* *
Q.9
(D) achiral
(K) chiral
(D)
(c)
O
COOH
Q.10
(i) achiral
(viii) chiral
(ii) achiral
(ix) achiral
(iii) chiral
(iv) chiral

1.
Diastereomer
2.
Identical (a & b); Diasteromer (a & b ; b & c)
3.
Diastereomer
4.
Diastereomer
5.
Identical
6.
Identical
7.
Identical
8.
Consitutional Isomer 9.
Diastereomer
10.
Enantiomer
11.
Enantiomer
12.
Diastereomer
Constitutional isomer 14.
15.
Constitutional isomer
13.
Consitutional isomer

1.
Enantiomer
5.
Enantiomer
6.
Enantiomer
7.
Diastereomer
8.
Consitutional Isomer
9.
Identical
10.
11.
Diastereomer
12.
Enantiomer
13.
14.
Identical
15.
Diastereomer

1.
Enantiomer
2.
Identical
3.
5.
Diastereomer
6.
7.
Enantiomer (b & c); Diasteromer (a & b ; b & c)
10.
11.
12.
13.
14.
Identical
15.
16.
8.
Identical
4.
Diastereomer 9.
Diastereomer
Identical

1.
2.
3.
4.
5.
6.
7.
Other
8.
9.
Other
10.
Other
11.
12.
13.
14.
15.
Enantiomer

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10

C2
C : The C2 axis lies along the Intersection of the 2 vertical -planes.
1.
N
2.
C2v
C2
H
H
C
3.
C2 D2d : 3 C2 axis with the 2 planes intersecting the principle (vertical) C2 axis.
C
C
H
C2 D6h : There are 3 pairs of vertical planes (not shown) and of C2 axis
C6
4.
intersecting the C6 axis. The C atoms lie in the horizontal -plane.

5.
6.
P.O.S. () ; C3
C2
7.
P.O.S.() ; C2 ; C3 ; S4 ; S2

1.
P.O.S. () ; C2
2.
P.O.S. () ; C2 ; C3 ; S4 ; S2
4.
P.O.S. () ; C2
5.
P.O.S. () ; C2
7.
C2
9.
C2
8.
C2
10.
6.
3.
P.O.S. () ; C2
P.O.S. () ; C2 ; S2
P.O.S. () ; C2 ; S2

S.NO.
1.
2.
3.
4.
5.
MESO
3
-
ACTIVE ISOMERS
2
4
8
16
TOTAL ISOMERS
5
4
2
8
16

Contact: 9414969800, 9549908816
11
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
15.
2
1
1
1
2
-
8
8
4
2
2
4
2
8
32
8
10
8
4
3
2
3
4
3
10
32
8

S.NO.
1.
2.
3.
4.
5.
6.
7.
8.
MESO
1
1
-
ACTIVE ISOMERS
2
4
2
16
32
4
TOTAL ISOMERS
3
4
3
16
2
32
3
4

S.NO.
1.
2.
3.
4.
5.
6.
7.
8.
9.
MESO
1
1
1
8
ACTIVE ISOMERS
2
16
16
16
2
2
2
4
128
TOTAL ISOMERS
3
16
16
16
3
2
3
4
136

S.NO.
1.
2.
3.
4.
5.
6.
MESO
1
1
ACTIVE ISOMERS
16
2
8
8
2
TOTAL ISOMERS
2
16
3
8
8
3

Contact: 9414969800, 9549908816
12
7.
8.
9.
10.
11.
4
4
2
2
128
4
4
2
2
136
1.
4.
7.
10.
13.
16.
Optically active:- OA Chiral molecule:- CM

Achiral molecule:- AM
Optically inactive:- OI
No. of chiral cente:- CC
AM, Ol, CC = 1
2.
OA, CM, CC = 0
3.
OA, CM, CC = 1
OA, CM, CC = 1
5.
OA, CM, CC = 0
6.
AM, Ol, CC = 2
OA, CM, CC = 2
8.
OA, CM, CC = 5
9.
AM, Ol, CC = 2
AM, Ol, CC = 4
11.
OA, CM, CC = 2
12.
OA, CM, CC = 2
OA, CM, CC = 3
14.
OA, CM, CC = 2
15.
AM, Ol, CC = 2
AM, Ol, CC = 2
1.
4.
7.
10.
13.
16.

AM, Ol, CC = 0
2.
AM, Ol, CC = 0
3.
AM, Ol, CC = 0
AM, Ol, CC = 2
5.
AM, Ol, CC = 3
6.
AM, Ol, CC = 0
OA, CM, CC = 0
8.
AM, Ol, CC = 0
9.
AM, Ol, CC = 0
AM, Ol, CC = 4
11.
OA, CM, CC = 2
12.
OA, CM, CC = 2
AM, Ol, CC = 2
14.
AM, Ol, CC = 2
15.
CM, OA, CC = 2
AM, Ol, CC = 2
1.
4.
7.
10.
13.
16.

AM, Ol, CC = 0
2.
OA, CM, CC = 0
3.
OA, CM, CC = 1
OA, CM, CC = 2
5.
OI, AM, CC = 0
6.
AM, Ol, CC = 0
OA, CM, CC = 3
8.
OA, CM, CC = 2
9.
AM, Ol, CC = 0
AM, Ol, CC = 0
11.
AM, Ol, CC = 2
12.
OA, CM, CC = 0
AM, Ol, CC = 0
14.
CM, OA, CC = 0
15.
AM, Ol, CC = 0
CM, OA, CC = 0
17.
CM, OA, CC = 2

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IIT-JEE CHEMISTRY BY N.J.

Answers for Isomeris DPP ( Conceptual Improvement of Isomerism )

Answers of DPP No. 1

Answers of DPP No. 2

Answers of DPP No. 3

(a) (1,2,3) CH3 CH2 CH2 CH2

CH2 CH3 (b)

CH3 CH2 CH CH CH3

CH2 = CH CH2 CH3,

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CH3 CH2 CH = CH2 ,

CH3 CH2 C CH, CH3 C C CH3,

(9) DBE = 2 C4H6

Answers of DPP No. 4

0.75 D = 0.3 X gauche

------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR

(a) i > ii > iii

(b) i > ii > iii

(a) 120 (b) < 10928

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

All Gauche All eclipsed

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Answers of DPP No. 6

Answers of DPP No. 7

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(3) (A) Cis

Answers of DPP No. 8

Answers of DPP No. 9

(A) = Keq < 1

Answers of DPP No. 10

(C) Keq > 1

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No. of POS = 4C2 = 6

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Answers of DPP No. 11

(i) 2 (ii) 3 (iii) 4 (iv) 10

(d) 3 > 1 > 2 > 4

(a) 1 > 3 > 2 > 4

(b) 2 > 1 > 3 > 4

(e) 3 > 1 > 2 > 4

(c) S (d) S (e) R

(c) 2 > 1 > 4 > 3

(g) 4 > 3 > 2 > 1

Answers of DPP No. 12

A S,P; B Q; C S,P; D S,R;

Answers of DPP No. 13

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Answers of DPP No. 16

Identical (a & b); Diasteromer (a & b ; b & c)

Constitutional isomer 14.

Answers of DPP No. 17

Answers of DPP No. 18

Enantiomer (b & c); Diasteromer (a & b ; b & c)

Answers of DPP No. 19

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Answers of DPP No. 20