Conceptual Improvement Isomerism Answers PDF

IIT-JEE ChEmistry by N.J.
sir ORGANIC chemistry

Answers for Isomeris DPP ( Conceptual Improvement of Isomerism )
Answers of DPP No. – 1
Q.1(a) Identical (b) Position(c) Position(d) Functional (e) Position
(f) Position (g) Chain (h) Position (i) Position (j) Functional
(k) Functional (l) Functional (m) Functional (n) Functional (o) Functional
(p) Chain (q) Ring chain (r) Chain
Q.2(a) Metamers (b) Identical (c) Metamers (d) Metamers (e) Functional
(f) Functional (g) Functional (h) Metamers
Q.3 A-Q, B-Q, C-R, D-S
1. Position isomers 2. Metamers 3. Positional 4. Chain
R
5. Identical 6. Functional 7. Functional
8. Functional 9. Non-identical 10. Non-identical
11. Ring chain 12. Non-identical / homologous
13. Position isomers 14. Chain isomers 15. Position 16. Metamers
17. Chain 18. Position 19. Position 20. Identical
21. Identical 22. Functional
1.
8.
Q.15
Q.16.
C
B
D
2.
9.
1°
D
B
2°
3.
10.
(a) (1°,2°,3°) CH3 — CH2 — CH2 — CH2

2° SI
B
C
2°
CH3 — CH2 — CH — CH — CH3

1° 2° 3°
4.
Q.11 D
2°
B 5.
Q.12 C
1°
CH2 — CH3 (b)
3°
4-ethyl-3-methyloctane
1°
C
2°
2°
2°
6.
Q.13
2°
2°
2°
2°
3° 3° 2°
2°
2°
3°
2°
1°
CH3
2°
A
C
7.
Q.14
(1°,2°,3°)
C
C
J.
CH
3
CH3
1° 1°
1,2,7-trimethylcyclopentadecane
1° 1° 1°
3°
CH3 4°
1° 1°
2°
CH3
2° 3° 2°
(c) (1°,2°,3°, 4°) 4° CH3 (d) (1°,2°,3°, 4°)
2° 1° 2°
3° 2°
N.
CH3 3°
1° CH3
1,1,2,5-tetramethylcyclopentane
1°
Q.17 (5) DBE = 1 CH2 = CH — CH2 — CH3, CH3 — HC = CH — CH2, , ,
CH3 — C = CH 2
CH3
OH
O
Q.18 DBE = 1 (5)C3H6O CH3 — CH2—C , CH3 — C — CH 3 , ,
H O
CH2 = CH — CH2 — OH, CH2 = CH — O — CH3
1
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Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360
Q.19 (5) DBE = 1 CH3—CH2—CH2—HC=CH2, CH3—CH2—HC=CH — CH3, CH3 — CH2 — CH = CH2 ,
CH3
, CH3—CH=C—CH3 , CH2=CH—CH—CH3 ,
CH3 CH3 ,
Q.20 (9) DBE = 2 C4H6 CH3 — CH2 — C  CH, CH3 — C  C — CH3, CH2=CH —CH = CH2,
CH3 — CH = C = CH2, , , , , ,
O O O O
Q.21 (4) C — CH2 — OH , CH3 — C , H — C — O — CH3 , ,
OH
R
H O—H
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
Q.4
Q.9
A Q.5
CH3–CH2–CH2–Br
C
H
H
Q.6
Br
CH3
H
H
SI
(f) = 2 = 5 (g) = s2 = 7
C Q.7
Q.10
D Q.8
CH3 — CH — CH3
CH3
H
CH3
Et
Et
CH3
H
CH3
CH3
H
H
J.
H
Cl Cl
H Cl H H
Q.11 (a) (gauche) , (anti) (b) 1, 2
H H H H
H Cl
7.5
Q.12 C Q.13 A Q.14 0.75 D = 0.3 X gauche gauche = = 2.5 D.
N.
3
Q.15 a>c>b
Et CH 3
H H C2H5 H
Q.16 CH3—CH2—CH—CH2—CH3 (a) (b) CH 3—CH 2—CH—CH 2—CH 2—CH 3
H C2H5
H CH3
CH3 CH3 H
CH3
+ O
O–H O N(Me)3
C
H C—H H O CH3 H CH3 CH3 CH3
Q.17 Q.18 Q.19 N O
H H H H H H H
H H H H
2
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Mob. No. : 9214233360
Q.20 T 
CH3 CH3 Et
H H CH3 H CH3 H
Q.21 (a) gauche (b) anti Q.22 (a) (b) (c)
CH3 H H CH3 H CH3
CH3 CH3 CH3
Ph Ph
CH3 H CH3 H
(d) (e)
H CH3 H CH3
Ph CH3
Q.23 (a) i > ii > iii (b) i > ii > iii (c) 3 > 2 > 1 > 4 (d) i > ii > iii (e) i > ii
R
1
Q.1 (a) 120° (b) < 109°28 (c) 0° (d) 60° Q.2 C Q.3 B Q.4 D
Q.5 E



 Keq = 18
x 100-x
Q.6
Q.13
100  x
H
x
H
= 18
18 × = 100 – x
19 × = 100
X = 100/19
C Q.7
C
D
O
H
O
Q.8
Q.14
C
SI +1
E
Q.9 B
+1
C/A
Q.10 B
+1
B/D/F
Q.11
+1
B
A, B, D Q.12
+1
E
B
J.
H H
Anti All Gauche All eclipsed Highest in Lowest in
H
energy energy
F
Q.15 


 Keq = 1.5
F
x 100-x
N.
100  x
= 1.5
x
1.5 × = 100 – x
25 × = 100
100
X= ×10
25
= 40%
Q.16 C
Q.1 A – P, R; B – Q, S; C – P, R; D – Q, R Q.2 (IV) > (III) > (I) > (II) Q.3 B
Q.4 Xanti = 3/4
3
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Mob. No. : 9214233360
OH
OH HO
Q.5 (a) and
HO
OH
(b) HO and
OH
OH
(c) and
R
(d) and
(e) and
(f)
(g)
SI and
and
J.
(h) and
Cl Cl
Cl
Cl Cl Cl
Cl
Q.6 (a) (b) Cl Cl Q.7
Cl Cl Cl
N.
Q.8 c>d>b>a Q.9 (a) (b)
Trans Cis Cis Trans

Q.1 (1) Z (2) Z (3) E (4) Z (5) Z (6) E (7) E (8) Z (9) Z (10) E (11) Z (12) Z (13) E
(14) E (15) Z (16) E (17) E (18) E (19) Z (20) E (21) Z (22) E (23) E (24) Z
Z
Z
(25) Z (26) Z Z (27) E (28) E (29) Z
Z Z Z
4
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Mob. No. : 9214233360
Q.2 (1) (A) X (B) X (C)  (D) X (E)  (F) 
(2) (A) X (B)  (C)  (D) X
(3) (A) Cis (B) Trans (C) Cis (D) Cis (E) Trans (F) Cis (G) Trans
(H) Trans (I) Cis (J) X (K) Trans (L) Cis
(4) (A) X (B) X (C)  (D) 

Q.1 (1) 21 (2) 23 (3) 23 (4) 23 (5) 22 (6) 22 (7) 23–1 +2(3–1)/2=6 (8) 23–1 + 2(3–1)/2 = 6 (9) 23
2–1 2/2–1 1 1 1 1 1 1 1 4
(10) 2 + 2 =2+1=3 (11) 2 (12) 2 (13) 2 (14) 2 (15) 2 (16) 2 (17) 2 (18) 2
3–1 (3–1)/2 3
(19) 2 +2 =6 (20) 2 = 8 (21) 21 (22) 2 (23) 22 = 4 (24) 2 (25) 2 (26) 21 (27) 23
(28) 22 (29) 22 (30) 22 (31) 4 (32) 22 (33) 21
Q.2 Trans Q.3 Trans
R
Q.4 (A) 23–1 + 2(3–1)/2 = 6
(B) 21 = 2
(C) 21 = 2
(D) 22 = 4
(E) 21= 2
Q.5 B, C Q.6 B
Q.1
Q.6
Q.8
Q.9
A
D
(A) 
(N) 
B
Q.2
Q.7
(B) 
Q.10
C
(A), (B)
B
Q.3
(C) X (D) 
Q.11
SI
D
(E) 
B
Q.4
(F) X
Q.12
(A) 22 (B) 2 (C) 2 (D) 23 (E) 21 (F) 21
(G)  (H) 
(A) = Keq < 1

(I)  (J) X
(B) Keq = 1
(K) 
Q.5
(L) 
(C) Keq > 1

A,B,C
(M) 
(D) Keq = 1
J.
Compound P.O.S. C.O.S. Optically active
1.
CH3 CH3  X X
N.
H H
2.
H CH3 X X 
CH3 H
5
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Mob. No. : 9214233360
3. H
H
 X X
CH3
CH3
H H
4.  X X
CH3 CH3
H H
R
5.
 X X
Cl Cl
6. Cl H
7.
H
Cl
H
Br
Cl
Cl
Cl
SI X
 
X
X

J.
H
8. H
Cl  X X
H
Cl
Cl
N.
9. H H X X
C=C=C 
Cl Cl
10. H Cl X X 
C=C=C
Cl Br
11. H H X X
C=C=C=C 
Cl Cl
12. H H
C C  X X
Cl Cl
6
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Mob. No. : 9214233360
13. Cl H
C C   X
H Cl
14. H H X X 
Cl Cl
15. H
CH 3   X
CH3
R
H
16. Cl H   X
H Cl
17.
18.
H
CH3
C
Cl
CH3
SI  X
X
X
X
J.

C
H H
CH3 CH3
19.
N.
X X 
C
H Cl
20.
 X X
7
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Mob. No. : 9214233360
21. X X 
22. Cl I
X  X
I Cl
R
23.
  X
 X X
24. O = C = O
25.
26.
27.
O=C=O
H
O=C=O
N=N=N
H
H
H
SI X
X
 X
X
X

J.
H
 X X
28. C No. of POS = 4C2 = 6
H H
H
H
29. C No. of POS = 3  X X
N.
Cl H
H
H H
30.
C=C No. of POS = 2  X X
CH3 CH3
CH3 H
C=C   X
31. No. of POS = 1
H CH3
8
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Mob. No. : 9214233360
Q.1 (i) 2 (ii) 3 (iii) 4 (iv) 10 Q.2 (a) 1 > 3 > 2 > 4 (b) 2 > 1 > 3 > 4 (c) 2 > 1 > 4 > 3
(d) 3 > 1 > 2 > 4 (e) 3 > 1 > 2 > 4 (f) 4 > 2 > 3 > 1 (g) 4 > 3 > 2 > 1
Q.3 (a) R (b) R (c) S (d) S (e) R (f) S (g) R (h) S (i) S (j) S (k) S (l) R (m) S
(n) R (o) S (p) S (q) R, R (r) R, R (s) S, R (t) R, S (u) R, S
Q.4 (a) R (b) R (c) S (d) S (e) R (f) S (g) R (h) S (i) S (j) S (k) S (l) R (m) S
(n) T (o) S (p) S (q) R,R (r) S,R (s) S, R (t) R, S (u) R, S
(v) R, S (w) R, S (x) R, S (y) R, R, R (z) R
R
Q.1 A  Q; B Q; C R,S; D Q; Q.2 A  T,P,S; B T, P; C S; D Q;
Q.3 B Q.4 Q.5 D
Q.6 A-B = Enantiomer, C-D = Enantiomer, A-C, A-D = distereomers, B-C & B-D = disteromers
Q.7 A Q.8 8 Q.9 5 Q.10 Q.11 C Q.12 Q.13
Q.14 (a) 4 (b) 4 (c) 7
Q.1
Q.3
Q.10
Q.14
Q.15
A  S,P; B Q; C S,P; D S,R;
A Q.4 C
Q.11 A, B, D
(a) diastereomers
(e) enantiomers
No-sym. Present
(i)
(ii)
(iii)
Q.5 A
SI
Q.6
Q.12
(b) distereomers
(f) distereomers
optical isomers = 27 = 128.

optically active = 2n = 27 = 128
meso = 0
Q.2
A
A  T; B S,R; C P; D T;
Q.7
Q.13 4
A
(c) distereomers
Q.8 C Q.9
(d) distereomers
D
J.
2n 128
(iv) enantiopair  = 64.
2 2
Q.1 A  Q, R; B  S, R, T; C  Q, R, T; D  P, Q;
Q.2 A  P, R; B  S; C  P, R, S; D  Q;
Q.3 B Q.4 D Q.5 B Q.6 (A) X (B) X (C)  (D) 
Q.7  = 125°
N.
Q.8 (A) chiral (B) achiral (C) achiral (D) achiral (E) chiral (F) achiral (G) chiral
(H) achiral (I) chiral (J) chiral (K) chiral (L) chiral (M) achiral
H
N: H
*
* * N O
Q.9 (a) – 12.5° (b) + 8.6° (c)
O
COOH
Q.10 (i) achiral (ii) achiral (iii) chiral (iv) chiral (v) achiral (vi) achiral (vii) chiral
(viii) chiral (ix) achiral
1. Diastereomer 2. Identical (a & b); Diasteromer (a & b ; b & c) 3. Diastereomer
9
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Mob. No. : 9214233360
4. Diastereomer 5. Identical 6. Identical 7. Identical
8. Consitutional Isomer 9. Diastereomer 10. Enantiomer 11. Enantiomer
12. Diastereomer 13. Constitutional isomer 14. Consitutional isomer
15. Constitutional isomer
1. Constitutional isomer 2. Constitutional isomer 3. Constitutional isomer 4. Enantiomer
5. Enantiomer 6. Enantiomer 7. Diastereomer
8. Consitutional Isomer 9. Identical 10. Constitutional isomer
11. Diastereomer 12. Enantiomer 13. Constitutional isomer
R
14. Identical 15. Diastereomer
1. Enantiomer 2. Identical 3. Identical 4. Diastereomer
5. Diastereomer 6. Constitutional isomer
7.
10.
13.
16.
1.
4.
Constitutional isomer
SI
Enantiomer (b & c); Diasteromer (a & b ; b & c)
11.
14.
8.
Identical

2.
5.
Diastereomer 9.
12.
15.
Identical
3.
6.
J.
7. Other 8. Constitutional isomer 9. Other
10. Other 11. Constitutional isomer 12. Constitutional isomer
13. Constitutional isomer 14. Constitutional isomer 15. Enantiomer
C2
N.
1. C : The C2 axis lies along the Intersection of the 2 vertical -planes.

N
2. C2v
10
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Mob. No. : 9214233360
C2
H H
C
3. C C2 D2d : 3 C2 axis with the 2 planes intersecting the principle (vertical) C2 axis.
C
H H
R
4. C6 C2 D6h : There are 3 pairs of vertical  planes (not shown) and of C2 axis
5.
1.
4.
7.
P.O.S. () ; C3
P.O.S. () ; C2
P.O.S. () ; C2
C2 8. C2
6.
2.
5.
9.
SI
intersecting the C6 axis. The C atoms lie in the horizontal -plane.
C2 7.
P.O.S. () ; C2
C2 10.
P.O.S.() ; C2 ; C3 ; S4 ; S2
P.O.S. () ; C2 ; C3 ; S4 ; S2
6.
3. P.O.S. () ; C2
P.O.S. () ; C2 ; S2
P.O.S. () ; C2 ; S2
J.
S.NO. MESO ACTIVE ISOMERS TOTAL ISOMERS
1. 3 2 5
2. - 4 4
3. - - 2
4. - 8 8
5. - 16 16
N.
6. 2 8 10
7. - 8 8
8. - 4 4
9. 1 2 3
10. - - 2
11. 1 2 3
12. - 4 4
13. 1 2 3
14. 2 8 10
15. - 32 32
15. - 8 8
11
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Mob. No. : 9214233360
1. 1 2 3
2. - 4 4
3. 1 2 3
4. - 16 16
5. - - 2
6. - 32 32
7. - - 3
8. - 4 4
R
1. 1 2 3
2. - 16 16
3. - 16 16
4.
5.
6.
7.
8.
9.
S.NO.
-
1
-
1
-
8
MESO
SI 16
2
2
2
4
128

ACTIVE ISOMERS
16
3
2
3
4
136
TOTAL ISOMERS
J.
1. - - 2
2. - 16 16
3. 1 2 3
4. - 8 8
5. - 8 8
6. 1 2 3
N.
7. - 4 4
8. - 4 4
9. - 2 2
10. - 2 2
11. 8 128 136
Optically active:- OA Chiral molecule:- CM Achiral molecule:- AM Optically inactive:- OI
No. of chiral cente:- CC
1. AM, Ol, CC = 1 2. OA, CM, CC = 0 3. OA, CM, CC = 1
4. OA, CM, CC = 1 5. OA, CM, CC = 0 6. AM, Ol, CC = 2
12
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Mob. No. : 9214233360
16. AM, Ol, CC = 2
1. AM, Ol, CC = 0 2. AM, Ol, CC = 0 3. AM, Ol, CC = 0
4. AM, Ol, CC = 2 5. AM, Ol, CC = 3 6. AM, Ol, CC = 0
7. OA, CM, CC = 0 8. AM, Ol, CC = 0 9. AM, Ol, CC = 0
13. AM, Ol, CC = 2 14. AM, Ol, CC = 2 15. CM, OA, CC = 2
16. AM, Ol, CC = 2
R
4.
7.
10.
13.
16.
OA, CM, CC = 2
OA, CM, CC = 3
AM, Ol, CC = 0
AM, Ol, CC = 0
CM, OA, CC = 0
SI
5.
8.
11.
14.
17.
OI, AM, CC = 0
OA, CM, CC = 2
AM, Ol, CC = 2
CM, OA, CC = 0
CM, OA, CC = 2
6.
9.
12.
15.
AM, Ol, CC = 0
AM, Ol, CC = 0
OA, CM, CC = 0
AM, Ol, CC = 0
J.
N.
13
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Mob. No. : 9214233360

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IIT-JEE ChEmistry by N.J.

sir ORGANIC chemistry

(a) (1°,2°,3°) CH3 — CH2 — CH2 — CH2

CH3 — CH2 — CH — CH — CH3

Q.17 (5) DBE = 1 CH2 = CH — CH2 — CH3, CH3 — HC = CH — CH2, , ,

Q.8 c>d>b>a Q.9 (a) (b)

Trans Cis Cis Trans

(2) (A) X (B)  (C)  (D) X

(4) (A) X (B) X (C)  (D) 

Q.2 Trans Q.3 Trans

(A) = Keq < 1

(C) Keq > 1

Answers of DPP No. – 12

optical isomers = 27 = 128.

Answers of DPP No. – 19

1. C : The C2 axis lies along the Intersection of the 2 vertical -planes.

Answers of DPP No. – 25

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