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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

Answers of DPP No. – 2

1. Position isomers 2. Metamers 3. Positional 4. Chain
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

Answers of DPP No. – 3

1. C 2. D 3. B 4. B 5. C 6. A 7. C
8. B 9. B 10. C Q.11 D Q.12 C Q.13 C Q.14 C
Q.15 D
2° 1°
2° 2° CH3
2° 3°
1° 2° 2° 2° 2° 1° 2° 2°
Q.16. (a) (1°,2°,3°) CH3 — CH2 — CH2 — CH2 CH2 — CH3 (b) (1°,2°,3°)
2° 2°
2°
CH3 — CH2 — CH — CH — CH3 2°
3° 3°
2° 2°
1° 2° 3° 3° 1°
4-ethyl-3-methyloctane CH CH3
1° 3 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°
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 = CH2
CH3

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 OH
O
Q.18 DBE = 1 (5)C3H6O CH3 — CH2—C , CH3 — C — CH3 , ,
H O
CH2 = CH — CH2 — OH, CH2 = CH — O — CH3
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 , ,
O—H OH
H
Answers of DPP No. – 4
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) π = 2, σ = 30 (b) π = 5 σ = 17 (c) π = 3 σ = 34
(d) π = 4 σ = 27 (e) π = 4 σ =3 (f) π = 2 σ = 5 (g) π = s2 σ = 7
Et
Et
Q.4 A Q.5 C Q.6 C Q.7 D Q.8
H
CH3 CH3
Br CH3
H H H H
Q.9 CH3–CH2–CH2–Br Q.10 CH3 — CH — CH3
H H CH3 H
CH3 CH3 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 µgauche µgauche = = 2.5 D.
3
Q.15 a>c>b
Et CH3
H H C2H5 H
Q.16 CH3—CH2—CH—CH2—CH3 (a) (b) CH3—CH 2—CH—CH 2—CH 2—CH 3
H C2H5
CH3 H CH3 CH3 H
CH3

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 + 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
Q.20 T↑ µ↑
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
Answers of DPP No. – 5
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
100 − x
= 18
x
18 × = 100 – x
19 × = 100
X = 100/19
Q.6 C Q.7 D Q.8 C Q.9 B Q.10 B Q.11 A, B, D Q.12 B
H O
C H
O +1 +1 +1 +1 +1
H
Q.13 Q.14 E C/A B/D/F B E
H H
Anti All Gauche All eclipsed Highest in Lowest in
H
energy energy
F

Q.15 Keq = 1.5

F
x 100-x
100 − x
= 1.5
x
1.5 × = 100 – x
25 × = 100
100
X= ×10
25
= 40%
Q.16 C
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 Answers of DPP No. – 6
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

OH
OH HO
Q.5 (a) and
HO
OH

(b) HO and
OH
OH

(c) and

(d) and

(e) and

(f) and

(g) and

(h) and

Cl Cl
Cl
Cl Cl Cl
Cl
Q.6 (a) (b) Cl Cl Q.7
Cl Cl Cl

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

Trans Cis Cis Trans

Answers of DPP No. – 7

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

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 Z
Z
(25) Z (26) Z Z (27) E (28) E (29) Z

Z Z Z

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) √

Answers of DPP No. – 8
1 3 3 3 2 2 3–1 (3–1)/2 3–1 (3–1)/2 3
Q.1 (1) 2 (2) 2 (3) 2 (4) 2 (5) 2 (6) 2 (7) 2 +2 =6 (8) 2 + 2 =6 (9) 2
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 1 2 1 3
(19) 2 +2 =6 (20) 2 = 8 (21) 2 (22) 2 (23) 2 = 4 (24) 2 (25) 2 (26) 2 (27) 2
2 2 2 2 1
(28) 2 (29) 2 (30) 2 (31) 4 (32) 2 (33) 2
Q.2 Trans Q.3 Trans
3–1 (3–1)/2
Q.4 (A) 2 + 2 =6
1
(B) 2 = 2
1
(C) 2 = 2
2
(D) 2 = 4
1
(E) 2 = 2
Q.5 B, C Q.6 B
Answers of DPP No. – 9
2 3 1 1
Q.1 A Q.2 C Q.3 D Q.4 (A) 2 (B) 2 (C) 2 (D) 2 (E) 2 (F) 2 Q.5 A,B,C
Q.6 D Q.7 (A), (B)
Q.8 (A) √ (B) √ (C) X (D) √ (E) √ (F) X (G) √ (H) √ (I) √ (J) X (K) √ (L) √ (M) √
(N) √
Q.9 B Q.10 B Q.11 B Q.12 (A) = Keq < 1 (B) Keq = 1 (C) Keq > 1 (D) Keq = 1

Answers of DPP No. – 10

Compound P.O.S. C.O.S. Optically active

1.

CH3 CH3 √ X X

H H

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2.
H CH3 X X √

CH3 H

3. H
H
√ X X
CH3
CH3

H H
4. √ X X

CH3 CH3

5. H H
√ X X

Cl Cl

6. Cl H
√ √ X

H Cl

7. Br

Cl H X X √
Cl
H Cl
H
8. H
Cl √ X X
H
Cl
Cl

9. H H
C=C=C X X √
Cl Cl

10. H Cl X X √
C=C=C
Cl Br

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11. H H
C=C=C=C √ X X
Cl Cl

12. H H
C C √ X X
Cl Cl

13. Cl H
C C √ √ X
H Cl

14. H H X X √
Cl Cl

15.
H
CH 3 √ √ X
CH3

16. Cl H √ √ X
H Cl

17.
√ X X

C
H Cl
CH3 CH3
18.

√ X X

C
H H

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 CH3 CH3
19.

X X √

C
H Cl

20.
√ X X

21. X X √

22. Cl I

X √ X

I Cl

23.
√ √ X

√ X X
24. O = C = O

25. H
O=C=O √ X X

H H
26. O=C=O X X √

27. X X √
N=N=N
H H

H
28. C No. of POS = 4C2 = 6 √ X X
H H
H

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 H
29. C No. of POS = 3 √ X X

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

Answers of DPP No. – 11

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

Answers of DPP No. – 12

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

Answers of DPP No. – 13

Q.1 A → S,P; B → Q; C → S,P; D → S,R; Q.2 A → T; B → S,R; C → P; D → T;
Q.3 A Q.4 C Q.5 A Q.6 A Q.7 A Q.8 C Q.9 D
Q.10 Q.11 A, B, D Q.12 Q.13 4
Q.14 (a) diastereomers (b) distereomers (c) distereomers (d) distereomers
(e) enantiomers (f) distereomers
Q.15 No-sym. Present
(i) optical isomers = 27 = 128.
(ii) optically active = 2n = 27 = 128
(iii) meso = 0
2n 128
(iv) enantiopair = = 64.
2 2
Answers of DPP No. – 14
Q.1 A → Q, R; B → S, R, T; C → Q, R, T; D → P, Q;
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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 α = 125°
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
Answers of DPP No. – 16
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 13. Constitutional isomer 14. Consitutional isomer
15. Constitutional isomer
Answers of DPP No. – 17
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
14. Identical 15. Diastereomer
Answers of DPP No. – 18
1. Enantiomer 2. Identical 3. Identical 4. Diastereomer
5. Diastereomer 6. Constitutional isomer
7. Enantiomer (b & c); Diasteromer (a & b ; b & c) 8. Diastereomer 9. Identical
10. Constitutional isomer 11. Constitutional isomer 12. Constitutional isomer
13. Constitutional isomer 14. Identical 15. Constitutional isomer
16. Constitutional isomer
Answers of DPP No. – 19
1. Constitutional isomer 2. Constitutional isomer 3. Constitutional isomer
4. Constitutional isomer 5. Constitutional isomer 6. Constitutional isomer
7. Other 8. Constitutional isomer 9. Other
10. Other 11. Constitutional isomer 12. Constitutional isomer
13. Constitutional isomer 14. Constitutional isomer 15. Enantiomer
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 Answers of DPP No. – 20
C2

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

N

2. C2v

C2

H H
C

3. C C2 D2d : 3 C2 axis with the 2σ planes intersecting the principle (vertical) C2 axis.

C
H H

4. C6 C2 D6h : There are 3 pairs of vertical σ planes (not shown) and of C2 axis

intersecting the C6 axis. The C atoms lie in the horizontal σ-plane.

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

Answers of DPP No. – 21
1. P.O.S. (σ) ; C2 2. P.O.S. (σ) ; C2 ; C3 ; S4 ; S2 3. P.O.S. (σ) ; C2
4. P.O.S. (σ) ; C2 5. P.O.S. (σ) ; C2 6. P.O.S. (σ) ; C2 ; S2
7. C2 8. C2 9. C2 10. P.O.S. (σ) ; C2 ; S2
Answers of DPP No. – 22
S.NO. MESO ACTIVE ISOMERS TOTAL ISOMERS
1. 3 2 5
2. - 4 4
3. - - 2
4. - 8 8
5. - 16 16
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 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
Answers of DPP No. – 23
S.NO. MESO ACTIVE ISOMERS TOTAL ISOMERS
1. 1 2 3
2. - 4 4
3. 1 2 3
4. - 16 16
5. - - 2
6. - 32 32
7. - - 3
8. - 4 4

Answers of DPP No. – 24

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

Answers of DPP No. – 25

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

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 7. - 4 4
8. - 4 4
9. - 2 2
10. - 2 2
11. 8 128 136
Answers of DPP No. – 26
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
7. OA, CM, CC = 2 8. OA, CM, CC = 5 9. AM, Ol, CC = 2
10. AM, Ol, CC = 4 11. OA, CM, CC = 2 12. OA, CM, CC = 2
13. OA, CM, CC = 3 14. OA, CM, CC = 2 15. AM, Ol, CC = 2
16. AM, Ol, CC = 2
Answers of DPP No. – 27
Optically active:- OA Chiral molecule:- CM Achiral molecule:- AM Optically inactive:- OI
No. of chiral cente:- CC
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
10. AM, Ol, CC = 4 11. OA, CM, CC = 2 12. OA, CM, CC = 2
13. AM, Ol, CC = 2 14. AM, Ol, CC = 2 15. CM, OA, CC = 2
16. AM, Ol, CC = 2

Answers of DPP No. – 28

Optically active:- OA Chiral molecule:- CM Achiral molecule:- AM Optically inactive:- OI
No. of chiral cente:- CC
1. AM, Ol, CC = 0 2. OA, CM, CC = 0 3. OA, CM, CC = 1
4. OA, CM, CC = 2 5. OI, AM, CC = 0 6. AM, Ol, CC = 0
7. OA, CM, CC = 3 8. OA, CM, CC = 2 9. AM, Ol, CC = 0
10. AM, Ol, CC = 0 11. AM, Ol, CC = 2 12. OA, CM, CC = 0
13. AM, Ol, CC = 0 14. CM, OA, CC = 0 15. AM, Ol, CC = 0
16. CM, OA, CC = 0 17. CM, OA, CC = 2

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