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(1)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. Answers of DPP No. – 2 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.. Answers of DPP No. – 3 4. B 5. C Q.11 D Q.12 C. B C. Q.16.. 1°. 2°. 2°. 2°. (a) (1°,2°,3°) CH3 — CH2 — CH2 — CH2. 2°. 1°. CH2 — CH3 (b). 2°. 3°. 3°. 4-ethyl-3-methyloctane. 2°. (c) (1°,2°,3°, 4°). 2°. 3°. 1°. (5) DBE = 1. 3°. 2° 3° 3°. 1°. A C. C C. 2°. 7. Q.14. CH3. (1°,2°,3°). 2°. CH3. CH. 1° 3 1° 1,2,7-trimethylcyclopentadecane. 1°. 1° 4° 2°. 1°. 3°. (d) (1°,2°,3°, 4°). 2° 2°. 2° 3°. CH3. 1° 1,1,2,5-tetramethylcyclopentane. Q.17. Metamers. 2°. 1°. CH3 3° 1° CH3 4° CH3. 16. Identical. 2°. 2° 2°. Chain. 1°. 2°. 2°. CH3 — CH2 — CH — CH — CH3. 1°. 2°. Functional. 4.. 6. Q.13 2°. 2°. Functional. CH2 = CH — CH2 — CH3,. CH3 1°. CH3 — HC = CH — CH2,. ,. ,. CH3 — C = CH2 CH3. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 1.

(2) OH O Q.18. DBE = 1 (5)C3H6O. CH3 — C — CH3 ,. ,. CH3 — CH2—C H. Q.19. ,. O. CH2 = CH — O — CH3 CH2 = CH — CH2 — OH, (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 Q.20. CH3 — CH2 — C ≡ CH, CH3 — C ≡ C — CH3,. (9) DBE = 2 C4H6 CH3 — CH = C = CH2,. ,. ,. (4). ,. ,. O. O Q.21. ,. CH3. C — CH2 — OH,. CH2=CH —CH = CH2,. ,. O. CH3 — C. ,. O. H — C — O — CH3 ,. OH. O—H. 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 CH3. Br Q.9. CH3–CH2–CH2–Br. H. H. H. H. H Q.10. CH3 — CH — CH3. Cl Q.11. Cl. H. H. ,. H. H. H. H. (anti). (b) 1, 2. H C. Q.13. Q.15. a>c>b. A. H H. Cl. H (a) (gauche). Q.12. CH3. CH3. CH3. H. Cl Q.14. 0.75 D = 0.3 X µgauche. µgauche =. 7.5 = 2.5 D. 3 CH3. Et H Q.16. CH3—CH2—CH—CH2—CH3 (a) CH3. C2H5. H (b) CH3—CH 2—CH—CH 2—CH 2—CH 3. H. CH3 CH3. CH3. H. H. C2H5 H. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 2.

(3) + N(Me)3. O–H O C—H. H. O. H. Q.17. O C. H. H. H. T↑. Q.20. Q.19. CH3 O. H. H. H. H. H. µ↑. CH3 Q.21. N H. H. H. CH3 CH3. H. CH3. Q.18. (a) gauche. (b) anti. Q.22. CH3. H. H. CH3. H. (a). CH3. Et H. CH3. H. (b). (c). CH3. H. CH3. H. CH3. CH3. CH3. Ph. Ph. H. CH3. H. CH3 (d). (e). H. H. CH3. CH3 CH3. Ph Q.23. (a) i > ii > iii. (b) i > ii > iii. Q.1 Q.5. (a) 120° (b) < 109°28 E. 1. (c) 0°. (c) 3 > 2 > 1 > 4 (d) i > ii > iii (e) i > ii Answers of DPP No. – 5 (d) 60° Q.2 C Q.3 B. Q.4. D. Keq = 18 x. 100-x. 100 − x = 18 x. Q.6. 18 × = 100 – x 19 × = 100 X = 100/19 C Q.7 D. H. O C. H. Q.8. C. H O. Q.13. Q.14. H. H. Q.9. Q.10. B. +1. +1. +1. E. C/A. B/D/F. Anti. H. B. All Gauche All eclipsed. Q.11. A, B, D Q.12. +1. B. +1. B. E. 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. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 3.

(4) Q.1 Q.4. A – P, R; B – Q, S; C – P, R; D – Q, R Xanti = 3/4. Answers of DPP No. – 6 Q.2 (IV) > (III) > (I) > (II). OH Q.5. Q.3. B. 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. Answers of DPP No. – 7 (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. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 4.

(5) Z. Z (25) Z. (26) Z. Z. 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. 1. 3. 3. 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. 3. 2. (F) Cis. (G) Trans. Answers of DPP No. – 8 2 3–1 (3–1)/2 3–1 (3–1)/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. Answers of DPP No. – 9 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. B. B. Q.12. (A) = Keq < 1. Q.11. (E) Trans (L) Cis. (D) √. Q.2 Q.7 (B) √. Compound. (29) Z. Z. (2) 2 (3) 2 (4) 2 (5) 2 (1) 2 2–1 2/2–1 1 (10) 2 + 2 =2+1=3 (11) 2 3–1 (3–1)/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 3–1 (3–1)/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. Z. (H) √. (I) √. (J) X. (B) Keq = 1. Answers of DPP No. – 10 P.O.S.. (K) √. Q.5. A,B,C. (L) √. (M) √. (C) Keq > 1. (D) Keq = 1. C.O.S.. Optically active. X. X. 1.. CH3 H. CH3. √. H. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 5.

(6) 2.. H. CH3. CH3. H. X. X. √. √. X. X. √. X. X. √. X. X. √. √. X. X. X. √. √. X. X. X. X. √. X. X. √. H. 3.. H CH3 CH3 H. H 4.. 5.. CH3. CH3. H. H Cl. Cl 6.. H. Cl. Cl. H. Br. 7.. H. 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. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 6.

(7) 11. H. Cl 12.. H Cl. 13.. 14.. H. C=C=C=C. √. X. X. √. X. X. √. √. X. X. X. √. √. √. X. √. √. X. √. X. X. √. X. X. Cl. C. C. H Cl. Cl. H C. C H. Cl. H Cl. H Cl. H. 15.. CH 3 CH3 H H Cl. 16. Cl. H. 17.. H 18.. C Cl. CH3. CH3. H. C. H. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 7.

(8) 19.. CH3. CH3. H. C. X. X. √. √. X. X. X. X. √. X. √. X. √. √. X. √. X. X. √. X. X. X. X. √. X. X. √. √. X. X. Cl. 20.. 21.. Cl. 22.. I. I. Cl. 23.. 24. O = C = O 25.. 26.. O=C=O H. H. O=C=O. H. 27.. N=N=N H. H. H C. 28.. H. H. No. of POS = 4C2 = 6. H. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 8.

(9) H C. 29.. Cl. H. No. of POS = 3. X. √. X. X. √. √. X. H C=C. CH3. No. of POS = 2. CH3. CH3 31.. X. H. H 30.. √. H C=C. H. No. of POS = 1. CH3. Answers of DPP No. – 11 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. Answers of DPP No. – 12 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. Answers of DPP No. – 13. 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. D. 2n 128 = = 64. 2 2 Answers of DPP No. – 14. B → S, R, T; C → Q, R, T; D → P, Q;. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 9.

(10) Q.2 Q.3 Q.7 Q.8. A → P, R; B Q.4 α = 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. H. * *. Q.9. (D) achiral (K) chiral. (D) √. N. O. (c). O COOH. Q.10. (i) achiral (viii) chiral. (ii) achiral (ix) achiral. (iii) chiral. (iv) chiral. 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. Constitutional isomer 14.. 15.. Constitutional isomer. 13.. Consitutional 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.. 5.. Diastereomer. 6.. Constitutional isomer. 7.. Enantiomer (b & c); Diasteromer (a & b ; b & c). 10.. Constitutional isomer. 11.. Constitutional isomer. 12.. Constitutional isomer. 13.. Constitutional isomer. 14.. Identical. 15.. Constitutional isomer. 16.. Constitutional isomer. 8.. Identical. 4.. Diastereomer 9.. Diastereomer Identical. 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. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 10.

(11) Answers of DPP No. – 20 C2. C : The C2 axis lies along the Intersection of the 2 vertical σ-planes.. 1. N. 2.. C2v C2 H. H C 3.. C2 D2d : 3 C2 axis with the 2σ planes intersecting the principle (vertical) C2 axis.. C C H. H. C2 D6h : There are 3 pairs of vertical σ planes (not shown) and of C2 axis. C6. 4.. intersecting the C6 axis. The C atoms lie in the horizontal σ-plane. 5.. 6.. P.O.S. (σ) ; C3. 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. 4.. P.O.S. (σ) ; C2. 5.. P.O.S. (σ) ; C2. 7.. C2. 9.. C2. 8.. C2. 10.. 6.. 3.. P.O.S. (σ) ; C2. P.O.S. (σ) ; C2 ; S2. P.O.S. (σ) ; C2 ; S2. Answers of DPP No. – 22 S.NO. 1. 2. 3. 4. 5.. MESO 3 -. ACTIVE ISOMERS 2 4 8 16. TOTAL ISOMERS 5 4 2 8 16. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 11.

(12) 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. Answers of DPP No. – 23 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. Answers of DPP No. – 24 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. Answers of DPP No. – 25 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. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 12.

(13) 7. 8. 9. 10. 11.. 8. 4 4 2 2 128. 4 4 2 2 136. Answers of DPP No. – 26. 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. Answers of DPP No. – 27. 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 = 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. Answers of DPP No. – 28. 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 = 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. ------------------------------------------------------------------------------------------------------IIT-JEE CHEMISTRY BY N.J. SIR A-833, Indra Vihar, near IL back door, Contact: 9414969800, 9549908816 web : symmetryiitjee.com. 13.

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