MS CHAUHAN ADVANCE

100 Between the two tautomers which is more stable ? (a) I (b) II (c) I = II (d) none of these OH O OH 131. (I) (II) (III) Correct stability order of the given tautomers is : (a) I > II > III (b) III > II > I (c) II > I > III (d) II > III > I OH O OH 132. (I) (II) (III) Correct stability order of the given tautomers is : (a) I > II > III (b) III > II > I (c) II > I > III (d) II > III > I OO OH O¯ O OH 133. 2+ x % ; y% O O¯ O OH z% O OH The correct order of enol contents x, y, z is : (a) x > y > z (b) z > y > x (c) y > x > z (d) x > z > y O OH 134. O x% ; OO y% O O OH O z % ( x, y, z represent enol content) OH The correct order of x, y, z is : (a) x > y > z (b) z > y > x (c) y > x > z (d) x > z > y OO O 135. CH3 (I) (II) CH3 (III) Among the given ketones, the one which does not enolize is : (a) I (b) II (c) III (d) none of these https://t.me/studyzee

101 CH3 136. C=O | H CH3 O D2O ODQ Product The product of this reaction should be : CD3 O (a) H (b) D H CH3 O (c) D (d) All of these 137. OO OO O (I) (II) (III) Among the given compounds, the correct order of enol content is : (a) I > II > III (b) III > II > I (c) II > I > III (d) II > III > I OO O O 138. OO (I) (II) (III) Among the given compounds, the correct order of enol content is : (a) I > II > III (b) III > II > I (c) II > I > III (d) II > III > I O O O 139. (I) (II) (III) Among the given compounds, the correct order of enol content is : (a) I > II > III (b) III > II > I (c) III > I > II (d) II > I > III 140. How many geometrical isomers are possible for the above compound ? (a) 3 (b) 4 (c) 6 (d) 8 https://t.me/studyzee

102 141. Which of the following compound will not show geometrical isomerism across the p-bond ? Cl Cl Me H (b) C (a) Me CH3 Cl Cl Br Br FF (c) (d) Br Br I I 142. H l1 H 143. H 144. C=C=C 145. H l2 Choose the correct relation between l1 and l2 ? (a) l1 = l2 (b) l1 > l2 (c) l1 < l2 (d) l2 = 2l1 (d) l2 = 2l1 H l1 H C=C=C=C H l2 H Choose the correct relation between l1 and l2 ? (a) l1 = l2 (b) l1 > l2 (c) l1 < l2 CH3 CH3 How many geometrical isomers are possible for the above compound ? (a) 0 (b) 2 (c) 3 (d) 4 CH3 C2H5 How many geometrical isomers are possible for the above compound ? (a) 0 (b) 2 (c) 3 (d) 4 CH3 146. CH3 How many geometrical isomers are possible for the above compound ? (a) 0 (b) 2 (c) 3 (d) 4 https://t.me/studyzee

103 CH3 147. Br How many geometrical isomers are possible for the above compound ? (a) 0 (b) 2 (c) 3 (d) 4 CH3 148. CH3 CH3 How many geometrical isomers are possible for the above compound ? (a) 0 (b) 2 (c) 3 (d) 4 CH3 CH3 149. How many geometrical isomers are possible for the above compound ? (a) 0 (b) 2 (c) 3 (d) 4 150. CH3 l1 CH3 CH3 l2 H H C=C=C=C HH C=C=C=C CH3 151. 152. (I) (II) 153. I and II are geometrical isomers of each other because (a) l1 = l2 (b) l1 > l2 (c) l2 > l1 (d) l1 and l2 cannot be compared. CH 2 = CH - CH = CH - CH = CH 2 How many geometrical isomers are possible for this compound ? (a) 2 (b) 3 (c) 4 (d) 8 CH 3 - CH = C- C = CH - CH 3 | | Br Cl How many geometrical isomers are possible for this compound? (a) 2 (b) 3 (c) 4 (d) 6 CH 3 - CH = C- C = CH - CH 3 | | Br Br How many geometrical isomers of this compound are possible ? (a) 2 (b) 3 (c) 4 (d) 6 .. N – OH RR 154. HO .. N N | .. R OH https://t.me/studyzee

104 (b) C 3 axis of symmetry (d) All of these (a) chiral (c) Optically active Cl Cl Cl Cl 155. Br Br Br Br (A) (B) Relationship between above pair (A) & (B) is : (a) Enantiomer (b) Diastereomers (c) Identical (d) Structural isomer CH3 H H Me 156. O NH2 O (B) NH2 (C) (D) (A) From the above compound (A), (B), (C) & (D) chiral compound is : (a) A (b) B (c) C (d) D 157. Which of the following compound is achiral ? CH2 CH2 CH2 CH2 (a) (b) CH2 CH2 CH2 CH2 CO2H CO2H CH2 CH2 H CO 2 (c) (d) CH2 CH2 CO2H https://t.me/studyzee

105 158. CH2–O–CH2–CH3 CH3—(CH2)4 CH CH (CH2)5–CH3 CH2–CH2–O–CH2–CH3 CH3—(CH2)4 (CH2)5–CH3 CH3 O (A) (B) R and S configuration of compound (A) & (B) will be : (a) R, R (b) R, S (c) S, R (d) S, S 159. Which of following compound has center of symmetry? Br O || CH2 CH2 H NH – C CH3 (a) CH2 (b) CH3 H C – NH CH2 || O Br Cl CH3 H (c) Cl (d) All of these H CH3 160. Which mixture of structure in each beaker would rotate plane polarized light ? CH3 H HO H H CH3 H OH (a) H H (b) (&) Cl H OH CH3 OH Cl CH3 https://t.me/studyzee

106 CH3 H OH H OH (c) CH3 CH3 (d) All of these H OH HH CH3 161. Which of following compound will rotate the plane polarized light at room temperature? (a) (b) (c) (d) 162. Which of the following having plane of symmetry ? H H H H H H (b) H (a) H H H (d) All of these H (c) H 163. Which of following compound is achiral ? Me O (a) O (b) Me O https://t.me/studyzee

107 (c) H H (d) All of these Cl Br Cl 164. Which of the following compound has plane of symmetry ? R = -CH - Cl , S = -CH - Cl | | CH3 Br R SR (a) R R (b) S S (c) S S (d) None of these RS R 165. Which of following is E isomer ? P C=C O (a) S S S O (b) S P OO (c) O C = C OO (d) OH O O O 166. Among the given pairs, in which pair second compound has less enol content than first compound? OO OO (a) O (b) O (c) (d) none of these 167. Which of the following is incorrect relation between given pairs ? NH2 + O OH NH2 (a) = Resonance (b) = Tautomers – https://t.me/studyzee

108 S S– R O R+ O+ R O R = Resonance = Tautomers (c) – H H (d) H O+ H O 168. || Ph — CH — C — H ¾H¾O¾Q ® (B) ; (A) and (B) are isomer and isomerization effectively 169. | H2O 170. OH ( A) carried out by trace of base (B). Identify (B). OO || || (a) Ph — CH 2 — C — O — H (b) Ph — C — O — CH 3 OO || || (c) Ph — C — CH 2 — OH (d) H — C — CH 2 — O — Ph CH 3 — CH == CH — CH == CH — CH 3; total number of geometrical isomer is : (a) 2 (b) 3 (c) 4 (d) 6 Identify most stable enol form of terric acid: O O OH CH3 O OH O O O (a) O O (b) O CH3 OH O O OH O (c) O (d)O O OH 171. Which structure is most stable ? OH O OO (b) (a) OH OH OH O (d) (c) https://t.me/studyzee

109 172. Identify conformer of 2-methly pentane : H CH3 H H H CH3 H CHEt3 HH (c) (a) (b) HH (d) HH H HH CH3 CH3 Et CH3 HH CH2CH3 173. The lowest energy conformer of is: CH3 H H (a) (b) (c) (d) Cl 174. Cl How many atoms will be bisect during plane of symmetry ? (a) 2 (b) 4 (c) 6 (d) 8 175. The number of all types of isomers of chlorobutane is : 176. (a) 2 (b) 4 (c) 6 (d) 5 Which of the following pairs of compounds are not positional isomers ? HO CH3 OH CH3 (a) and OH (b) and (c) CH3 CH3 OH CH2OH OCH3 and (d) All of these 177. Which of the following pairs of compounds are functional isomers ? and O OO (a) OH (b) and (c) OH O O and (d) O and O O https://t.me/studyzee

110 178. The isomeric alcohol which has a chiral carbon atom is: 179. (a) n-butyl alcohol (b) iso-butyl alcohol (c) sec-butyl alcohol (d) tert-butyl alcohol 180. 181. The pair of enantiomers among the following compound is: CH3 CH3 CH3 H Ph H H Br Ph Br Br CH3 Br Ph H Ph I II III IV (a) I and IV (b) II and IV (c) II and III (d) I and II Which of the following is chiral? (a) Cell phone (b) Spiral staircase (c) Scissor (d) All of these In which of the following compound, possess plane of symmetry as well as centre of symmetry? Cl Cl CH3 CH3 (a) (b) (c) (d) Cl CH3 CH3 182. Which of the following compound has one of the stereoisomers as a meso compound? (a) (b) (c) (d) 183. For the following Newman projection H Cl Cl HH H HH H Cl (a) Cl Cl (b) Cl H HH Cl H H H Cl (d) H (c) H H H Cl HH Cl H https://t.me/studyzee

111 184. Which of the following is correct for the given compound? O OO (a) It possess centre of symmetry (b) It possess C 4 axis of symmetry (c) It possess plane of symmetry (d) Compound is chiral 185. Which of the following molecules has axis of symmetry and a coaxial plane of symmetry? 186. 187. O Cl H H (c) C (a) H H Cl Cl Cl (d) (b) (e) All of these Number of diastereomer of given compound : CH3 H Cl H Cl H Cl CH3 (a) 2 (b) 3 (c) 4 (d) 6 Which of the structures is/are diastereomer of A ? O (1) (A) O (4) || (2) (3) O O || O (5) || (a) 3 O (b) 1 and 4 (c) 2 and 3 (d) 5 https://t.me/studyzee

112 188. Identify which of the structures below are meso structures ? O O O O O (1) (3) O || (2) || O O (4) O O || O O O || (5) O O (a) 1 and 3 (b) 1,3 and 5 (c) 1,3 and 4 (d) 2 and 5 189. O 190. || How many enol form is possible for CH 3 — CH 2 — C — CH 2 — CH 2 — CH 3 (including stereoisomers) will be ? (a) 2 (b) 3 (c) 4 (d) 5 Find the sum of all the stereocenters that are present in below compounds : H CH3 H CH3 H CH3 H CH3 CH3 CH3 CH3 CH3 H H CH3 CH3 (I) (III) H CH3 H CH3 (II) (IV) (a) 8 (b) 9 (c) 10 (d) 11 191. A pair of stereoisomers might be classified in various ways. Which of the following statement 192. are true with respect to pairs of stereoisomers ? 193. (a) They might be configurational isomers (b) They might be diastereomers (d) They might be tautomers (c) They might be constitutional isomers (f) They might be enantiomers (e) They might be conformational isomers (g) They might be positional isomers (a) a, b, c, e (b) b, d, e, f, g (c) a, b, f (d) a, b, c, f Ignoring specific markings, which of the following objects are chiral ? (I) a shoe (II) a book (III) a pencil (IV) a pair of shoes (consider the pair as one object) (V) a pair of scissors (a) I only (b) I & V (c) I, IV, V (d) III, IV, V Calculate the total number of stereoisomers when alkene having trans configuration : O (a) 2 (b) 3 (c) 4 (d) 8 https://t.me/studyzee

113 O || 194. ¾ D¾2O¾/ D¾O¾- ® (B) 195. 196. Prolonged (A) treatment After prolonged treatment of ( A) by D 2O DO - , the difference in molecular weights of compounds ( A) and (B) is : (a) 2 (b) 3 (c) 4 (d) 8 Cl2 A mixture of all isomers possible from the mono-chlorination of hn the structure is subjected to fractional distillation, then how many fractions will be obtained? (a) 2 (b) 3 (c) 4 (d) 5 Br OO Number of optically active isomer is/are : Br (a) 0 (b) 1 (c) 2 (d) 3 O 197. At normal temperature, X and Y OH OH O X Y (a) resonance structures (b) tautomers (c) functional isomers (d) positional isomers 198. Two possible stereoisomers for H COOH are HO H (a) enantiomers (b) diastereomers (c) conformers (d) rotamers 199. The configurations of the carbon atoms C 2 and C 3 in the following compound are 200. respectively COOH H OH OH H CHO (a) R, R (b) S, S (c) R, S (d) S, R The compound that is chiral is (a) 3-methyl-3-hexene (b) 4-chloro-1-methycyclohexane (c) 2-phenylpentane (d) 1, 3-disopropylbenzene https://t.me/studyzee

114 201. Number of optically active tartaric acid is/are possible : (a) 1 (b) 2 (c) 3 (d) 4 Br O O Number of optically active isomer is/are : 202. Br (a) 0 (b) 1 (c) 2 (d) 3 203. Correct relationship b/w pair of compounds. (1) and (2) and (3) and (a) 1-Conformer ; 2-Conformer ; 3-Conformer (b) 1-Conformer ; 2-Stereoisomers (GI) ; 3-Stereoisomers (GI) (c) 1-Conformer ; 2-Stereoisomers (GI) ; 3-Conformer (d) 1-Stereoisomerism (GI) ; 2-Stereoisomerism (GI) ; 3-Conformer CH3 204. Number of diastereomers possible for CH–CH3 (a) 1 (b) 2 (c) 4 (d) 0 BrH2C CH2–Br 205. H C CH No. of enantiomer = X Br Br H3C H HC CH No. of diastereomers = Y Br CH3 (c) 4 (d) 0 (b) 3 Sum X + Y = ? (a) 1 https://t.me/studyzee

115 ANSWERS – LEVEL 1 1. (b) 2. (c) 3. (b) 4. (c) 5. (a) 6. (b) 7. (c) 8. (d) 9. (c) 10. (d) 11. (b) 12. (c) 13. (a) 14. (b) 15. (b) 16. (d) 17. (c) 18. (a) 19. (b) 20. (b) 21. (d) 22. (b) 23. (c) 24. (d) 25. (a) 26. (b) 27. (d) 28. (b) 29. (a) 30. (c) 31. (c) 32. (a) 33. (b) 34. (c) 35. (c) 36. (d) 37. (c) 38. (d) 39. (b) 40. (a) 41. (a) 42. (d) 43. (a) 44. (d) 45. (a) 46. (b) 47. (c) 48. (b) 49. (c) 50. (c) 51. (d) 52. (d) 53. (e) 54. (a) 55. (d) 56. (c) 57. (d) 58. (b) 59. (a) 60. (a) 61. (c) 62. (d) 63. (e) 64. (d) 65. (b) 66. (b) 67. (d) 68. (d) 69. (d) 70. (d) 71. (d) 72. (a) 73. (b) 74. (a) 75. (b) 76. (b) 77. (a) 78. (b) 79. (c) 80. (b) 81. (d) 82. (a) 83. (b) 84. (a) 85. (a) 86. (d) 87. (a) 88. (d) 89. (a) 90. (b) 91. (a) 92. (a) 93. (b) 94. (a) 95. (b) 96. (b) 97. (a) 98. (d) 99. (b) 100. (a) 101. (c) 102. (c) 103. (c) 104. (d) 105. (d) 106. (a) 107. (c) 108. (b) 109. (d) 110. (a) 111. (c) 112. (c) 113. (a) 114. (d) 115. (b) 116. (b) 117. (c) 118. (d) 119. (b) 120. (c) 121. (a) 122. (b) 123. (d) 124. (b) 125. (b) 126. (c) 127. (c) 128. (b) 129. (d) 130. (a) 131. (c) 132. (d) 133. (d) 134. (d) 135. (b) 136. (b) 137. (c) 138. (a) 139. (d) 140. (b) 141. (b) 142. (a) 143. (c) 144. (b) 145. (b) 146. (b) 147. (b) 148. (a) 149. (b) 150. (c) 151. (a) 152. (c) 153. (b) 154. (d) 155. (c) 156. (a) 157. (c) 158. (d) 159. (d) 160. (d) 161. (b) 162. (d) 163. (d) 164. (d) 165. (d) 166. (c) 167. (d) 168. (c) 169. (b) 170. (c) 171. (c) 172. (d) 173. (b) 174. (c) 175. (d) 176. (c) 177. (b) 178. (c) 179. (c) 180. (d) 181. (d) 182. (b) 183. (b) 184. (c) 185. (e) 186. (b) 187. (b) 188. (a) 189. (c) 190. (c) 191. (c) 192. (b) 193. (c) 194. (c) 195. (b) 196. (a) 197. (b) 198. (a) 199. (a) 200. (c) 201. (b) 202. (a) 203. (c) 204. (d) 205. (d) https://t.me/studyzee

116 Column (II) Stereoisomers Level - 2 (p) 2 1. Match the Column (I) and (II). Column (I) Reaction (a) CH 3 — CH == CH — CH == N — OH (b) (q) 4 (c) CH 3 — CH == CH — CH == CH — CH == CH — CH 3 (r) 6 (d) CH 3 — CH == CH — CH == CH — CH == CH - Ph (s) 8 2. Match the Column (I) and (II). R Keq R Column (I) Column (II) Group Equilibrium Constant (a) R == — H (p) 38 (b) R == — CH 3 (q) 23 (c) R == — Et (r) 18 R == — CH — CH 3 (d) \\ (s) 1 CH3 https://t.me/studyzee

3. Match the Column (I) and (II). (Matrix) 117 Column (I) Column (II) Molecule Nature H CO2CH2CH2OH (a) (p) Chiral CO2H H HH CO2CH2CH2O2C (b) (q) Achiral CO2CH2CH2O2C HH OH H CO2H (c) (r) Meso CO2H H OH (s) Compound containing even H CO2H H number of chiral centers (d) HO CO2H OH https://t.me/studyzee

118 Column (II) 4. Match the Column (I) and (II). (Matrix) Isomerism Column (I) Geometrical isomerism Compound CH3 H (a) (p) H Et CH3 Et Optical isomerism (b) (q) HH D CH3 Et (c) H (r) Compound containing plane of symmetry HH CH3 CH3 CH3 (d) H (s) Compound containing center of symmetry HH https://t.me/studyzee

5. Match the Column (I) and (II). 119 Column (I) Molecules Column (II) Relationship (a) Cl and Cl Identical (p) CH3 CH3 (b) Cl and Cl Enantiomer (q) CH3 CH3 (c) Cl and CH3 (r) Diastereomer CH3 Cl Cl and Cl (d) CH3 (s) Structural Isomerism CH3 Column (II) Nature 6. Match the Column (I) and (II). (Matrix) Column (I) Compound CH3 Br OH CH3 (a) CH3 CH3 (p) cis-compound HO Br Br OH CH3 (b) CH3 CH3 (q) trans-compound (c) CH3 HO Br CH3 (r) Optically active CH3 (d) CH3 (s) Optically inactive CH3 https://t.me/studyzee

120 Column (II) Property 7. Match the Column (I) and (II). (Matrix) Chiral centers containing compound Column (I) Presence of stereocenter Molecule HH (a) C == C == C (p) Cl Cl H CH3 (b) (q) CH3 H Cl (c) Br F (r) Optically active compound I CH3 OH (d) C == N (s) Compound containing plane of symmetry Et 8. Match the Column (I) and (II). (Matrix) Column (I) Column (II) Property Molecule Polar molecule FH Optically active (a) C == C == C == C (p) HF FH (b) C == C == C (q) HF (c) F F (r) Optically inactive Plane of symmetry H HF (d) (s) H H H https://t.me/studyzee

9. Match the Column (I) and (II). (Matrix) 121 Column (I) Column (II) Molecule Property Me H Meso compound (a) (p) Me H (b) (q) Achiral H Me Me (r) Chiral compound H (s) Compound will show geometrical isomerism (c) H Me Me H (d) Me Me H H https://t.me/studyzee

122 Column (II) 10. Match the Column (I) and (II). Conformers Column (I) Fully eclipsed Modified Newmann Projection Partially eclipsed CH3CH3 (a) (p) Gauche HH H H Staggered H CH3 (b) (q) CH3 H HH CH3 (r) HH (c) HH CH3 CH3 H CH3 (d) (s) HH H https://t.me/studyzee

11. Match the Column (I) and (II). 123 Column (II) Column (I) Name of the Compound Newmann Projection (p) 3-methyl pentane CH3 H CH3 (a) HH CH3 CH3 CH3 (b) (q) n-butane H HH H CH3 H (c) (r) Methyl-cyclopentane H H CH3 H (s) 1,2,4-trimethyl cyclohexane H H (d) H H CH3 CH3 https://t.me/studyzee

124 Column (II) 12. Match the Column (I) and (II). (Matrix) Property Column (I) Molecule (a) (p) Rotates plane polarized light Cl (b) (q) Cannot rotate plane polarized light Br Cl Br (c) (r) Plane of symmetry AsMe3 Centre of symmetry CH3 I (s) (d) C == C == C Column (II) Stereocenters CH3 Cl (p) 1 13. Match the Column (I) and (II). Column (I) Molecule CH 3 — CH == CH — CH — CH 3 (a) | Br H — C ºº C — CH == CH — CH— CH— CH 3 | | (b) (q) 2 Br Br 3 4 O || (c) Ph — S— CH == CH — CH — CH 3 (r) | (s) CH3 Ph — CH — Et (d) | Cl https://t.me/studyzee

14. Match the Column (I) and (II). 125 Column (II) Column (I) Stereoisomers Molecule (p) 2 H C C COMe (a) H C C COMe (b) (q) 0 H C C COMe (c) (r) 4 H C C COMe (d) (s) 8 https://t.me/studyzee

126 15. Match the Column (I) and (II). (Matrix) Column (I) Column (II) Property Molecule Meso Compound O Me C — Me (a) Me (p) O Me OH Compound having even no. of Me2N C ºº C — Me chiral centres (b) O (q) (c) O (r) Optically active compound (s) Compound having odd no. of (d) H O chiral centres. H ON H COOH H OH H OH COOH https://t.me/studyzee

127 16. Match the Column (I), (II) and (III). (Matrix) Column (I) Column (II) Column (III) Property Molecule No. of Chiral Center CH3 CHDCl (a) C == C (p) Optically active (w) 0 HH (b) CH3 (q) Optically inactive (x) 1 CH3 (r) Plane of symmetry (y) 2 Os | — HCls (c) CH 3 —Å N | Et H H (s) Centre of (d) Cl symmetry (z) 3 Cl 17. CH3 O H (a) H3C CH3 (b) (c) CH3 H O CH3 H H HH CH3 CH3 (f) (d) C == C == C (e) C == C == C CH3 HH HH H Br CH3 OH OH (g) (h) CH3 CH3 CH3 OH Br H From the above compounds select : (A) two of which are chiral and contain chiral centre : (B) two of which are achiral and contains chiral centre : (C) two of which are chiral and does not contain chiral centre : (D) two of which are achiral and does not contain chiral centre : https://t.me/studyzee

128 Cl Cl Cl Cl Cl Cl 18. Comprehension Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl (P) (Q) (R) Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl (U) (S) (T) (d) T Consider the given structures and answer A, B & C. (d) U A. Which of the compound is optically active ? (a) P (b) R (c) S B. Which of the isomer is most stable ? (a) R (b) S (c) T 19. Identify relationship between following pairs : CO2H CO2H FH OH H H OH Cl Br Br Cl (a) (b) HF Cl OH HO Cl CO2H CO2H H CH3 OH OH F CH3 H (d) C—C (c) F H3C F F H H CH3 If they are enantiomer answer will be 1, if they are diastereomers answer will be 2, if they are constitutional isomers answer will be 3 and if they are identical present 4 as the answer. Sum of answer of each part a + b + c + d is : . . . . . . . . https://t.me/studyzee

129 20. In each of the following three questions a hydrocarbon is named. For each select from among the sixteen conformational structures (a through p) all structures that represent possible conformers of that compound. Write letters (a through p), corresponding to your selections, in each answer box. A. 2-methylbutane B. 2,3-dimethylpentane C. 1-ethyl-1, 3-dimethyl cyclohexane H H C H3 H CH3 H3C H (a) C H3 CH3 (c) (b) C 2H5 C H3 C H3 C 2H5 H H H3C H3C H HH C H3 H H CH3 H H CH3 (e) (d) H3C (f) H CH3 H C H3 C 2H5 C H3 H3C C H3 C H3 H C 2H5 CH3 HH C H3 C 2H5 (h) (i) (g) H3C C 2H5 H CH3 H3C C H3 C H3 H CH3 (k) H3C C 2H5 CH3 (j) H C2H5 (l) CH3 C 2H5 C2H5 H H CH3 C H3 H CH3 (n) CH3 (o) H3C C 2H5 (m) H H C H3 C H3 C 2H5 C2H5 H H CH3 H C2H5 H (p) H H H3C H CH3 https://t.me/studyzee

130 21. Examine structures a through j, shown below, with respect to their symmetry or lack of it. Assume that the five-membered rings and the ring in compound g are planar. The wedge-hatched bonds in b, c, d & e designate specific configurations. Also, for the acyclic compounds assume stable anti conformations. Answer each of the following questions by writing letters (a through j), corresponding to your selections, in each answer box. If there is no structure that fits the description enter an x in the answer box. A. Which structures are chiral ? B. Which structures have a plane of symmetry ? C. Which structures have a center of symmetry ? H OH Br Br (a) (b) (c) Br Cl Br Br Br Br OH (d) (e) (f) H O (g) (h) C2 H 5CHCl 2 (i) C2 H 5CHClC2 H 5 (j) C2 H 5CHClCH 3 22. (i) 1,2-dichlorocyclopropane = w (ii) 1,3-dimethyl-cyclobutane = x (iii) 2-bromo-3-chlorobutane = y (iv)1,3-dimethyl cyclohexane = z Calculate total number of stereoisomer of the above compounds. Sum of w + x + y + z = KK https://t.me/studyzee

131 23. Examine the following formulas and select those pairs that satisfy the following conditions : Be sure to write two letters (and only two) in each answer box, unless you select f. In the second and third parts more than one answer is possible. H C H3 (b) H3C C2H5 H3C C H3 H H H H (a) C H3 H H (c) H C 2H5 (e) CH3 H H3C C H3 H3C C H3 H H C H3 (f) No formulas meet the C2H5 designated condition (d) H H3C C H3 CH3 H A. Which are identical in all respects? B. Which are conformational isomers? C. Which are constitutional isomers? 24. Examine the following formulas and select those pairs that satisfy the following conditions : Be sure to write two letters (and only two) in each answer box. In the second and fourth parts more than one answer is possible. (a) Br Br (b) Br Br (c) H H H H H Br H Br Br H Br H H (f) Br (d) (e) H Br Br H Br H A. Which are identical in all respects? B. Which are configuration isomers? C. Which are conformational isomers? https://t.me/studyzee

132 25. Consider the following statements regarding the given projection (True or False). CH2Cl CH2Cl Cl H (W) H Br (X) H Cl Cl H CH3 CH3 CH2Cl H Cl CH3 H H Cl (Y) Cl Br (Z) CH3 H CH2Cl (a) W and Y are diastereomers (b) Z is the projection of X (c) W, X, Y and Z are optically active (d) Y and Z are isomer 26. Examine the following structural formulas and select those that are chiral. OH NH2 O (a) CN (b) (c) CO2H CO2H CN H OH H OH (d) (e) H OH (f) HO CH3 OH CH2 – CO2H CH2 – CO2H OH SO3H NO2 (g) CH3 (h) (i) CH3 CH3 C=C=C NO2 SO3H H H CH3 (j) H Cl H Cl CH3 Write your choice here https://t.me/studyzee

133 27. The configuration of eight compounds, a through h are shown below, using various kind of stereo representations. To answer the question given below, write (a through h) indicating your choice. H (b) O CºN C—H (c) HC º C — C CH(CH3)2 (a) CH3CH2 — C OH H CH3 C2H5 CH3 CO2H — CH2 — C Br CH3 OH (d) (e) (f) H H OH CH3 O CH3 H O H OH CH3 CH3 CH3 (g) (h) O O CH2 C H CH3 A. Which of these configuration are achiral? B. Which configuration has no stereogenic center? C. Which configuration has more than one stereogenic center? D. Which of these configuration are meso compound? 28. The structural formula of ten compounds, (I) through (X) are drawn below, you may select any one of these structure. Answer the following question about that compound. https://t.me/studyzee

134 CH3 II CH3 III HO I VI V CH3 IX CH3 CH3 CH3 CH3 CH3 CH3 IV VIII Et CH3 OH OH CH3 OH OH CH3 VII CH3 OH CH3 CH3 CH3 OH X OH CH3 A. How many chiral centre are present in this compound ? (a) 0 (b) 1 (c) 2 (d) 3 (e) 4 (f) 5 B. Is this compound chiral or achiral ? (a) Chiral (b) Achiral C. What symmetry element are present in this compound ? (a) None (b) Plane of symmetry (c) Center of symmetry 29. The structure of one of the enantiomers of the amino acid cysteine is shown below. 3 COOH 1 H2N H 4 R CH2SH 2 Classify this structure as : (b) D or L (a) R or S https://t.me/studyzee

135 30. Identify the following double bonds either E, Z or None (N) in the compounds given below either. A. 13 4 2 O H3CO H3CO 5 67 O B. (a) Bongkrekic acid is a toxic compound produced by Pseudomonas cocovenenans, and isolated from a mold that rows on bongkrek, a fermented Indonesian coconut dish. (a) Label each double bond as E, Z or neither (N). COOH 2 3 COOH 4 OCH3 COOH Bongkrekic acid 6 15 (b) How many total stereoisomers (including all types) are possible for bongkrekic acid ? .......... (c) How many sites of unsaturation are present in bongkrekic acid ? ................. https://t.me/studyzee

136 31. Designate the following double bonds as E, Z or none (N) configuration in the boxes provided below. NH2 O O 1 23 32. The following compounds may exist as two or more stereoisomers. These may be classified as enantiomer pairs or meso compounds. C6H5 CO2H C6H5 CO2H (a) (b) C6H5 CO2H HO2C C6H5 truxinic acid truxillic acid Cl Cl (c) CO2H (d) Cl Cl Cl Cl (e) C(CH 3CHCl)4 (f) CO2H Cl C = CHCO2H Cl CHCO2H Cl (g) (h) Cl Cl Answer the following question about the above structure. (A) Total number of stereoisomers : (B) Number of enantiomeric pairs : (C) Number of meso compounds : https://t.me/studyzee

137 33. Identify axis of symmetry in the given compound. Me Cl Et Me Cl Et Et (1) Cl (2) Et Me Me Et Cl Et Me O N O Me Cl OO N (4) (3) OO O Cl Cl O O N Me Cl Br Me3C N N Br (6) N CMe3 (5) Cl Br CMe3 Cl O OO O N NN (7) (8) OO ONO O Cl H O (10) (9) H Cl H Cl https://t.me/studyzee

138 OO Cl Cl (11) (12) (13) 34. For each of the following pharmaceutical compounds, identify all stereogenic (i.e., all asymmetric carbon atoms) and label the configuration of each as being either (R) or (S). O HO OH OH N(CH3)2 HO HO O O O O H (1) O O OCH3 (2) NCH3 O erythromycin HO morphine F O S O OH NH2 O N OH HO H H N (4) O FH (3) O HH HO flonase amoxicillin F HO O O OSO2NH2 O O O O O (5) (6) OO topomax zocor https://t.me/studyzee

139 35. Find relationship between given pair : Identical Enantiomer Diastereomer Constitutional Isomer 1. CO2H CO2H 2. OH OH 3. OH OH CH3 Et H OH HO H 4. H OH HO H Et CH3 H CH3 CH3 H 5. HH CH3 CH3 CH3 CH3 CH3 CH3 HH 6. H H CC H CH3 CH3 H 7. https://t.me/studyzee

140 8. CH3 H H CH3 9. CH3 H H CH3 10. 36. Comprehension Structural formula of compound ( A) is following: HO2C CO2H A. The correct statement(s) about the compound ( A) is/are: (a) The total number of stereoisomers possible for ( A) is 3 (b) The total number of mesoisomer possible for ( A) is 1 (c) The total number of pair of enantiomer possible for ( A) is 1 (d) All of these B. Number of plane of symmetry in cis-form of compound ( A) is: (a) 0 (b) 1 (c) 2 (d) 3 37. Match the column. (Matrix) Column (I) Column (II) No. of Carbon No. of structural isomer (a) C4H10 (p) 2 (b) C5H12 (q) 3 (c) C6H14 (r) 5 (d) C7H16 (s) 9 https://t.me/studyzee

38. Match the column. (Matrix) 141 Column (I) Column (II) Compound % of enol content (a) (p) 100 % O OO (b) (q) 76 % O (r) 8% (s) Keto-Enol is not possible OO (c) || || CH3 - C - CH2 - C - CH3 OO (d) || || CH3 - C - CH2 - C - O - Et 39. Draw a most stable conformation (N – C) bond in the following compound. H .. H H N—C = C HH 40. Find total number of stereoisomers for each compound given below : O || (1) Ph - S - CH = CH - CH 2 - CH = C = C = CH - CH = CH - CH 3 CH=CHI– CH3 Cl H (2) (3) Br CH3 NO2 Cl N–OH (4) Ph – CH – CH – NH – CH3 (5) | | OH CH3 O OO N–H || || O (6) H – O – C – CH – CH – C – H (7) || OH OH OH https://t.me/studyzee

142 Cl CH – CH = CH – CH 3 (8) (9) H (10) CH3 – CH = CH – CH –CH3 (11) CH – CH3 | Br 41. Find the total number of stereoisomer for each compound : (1) a b ¾® a (2) ¾® b b a b a (3) ¾® c (4) ¾® d a a a b a a (5) ¾® e (6) ¾® f b d a a 42. Match the column : Column (II) Isomeric Relationship Column (I) Pair CH3 O (p) || C—O (a) O Chain CH3 || C—O O || (b) CH3 - CH2 - CH2 - C - OH , CH3 - CH - CH3 (q) Positional | CO 2H https://t.me/studyzee

143 (c) , NO2 (r) Functional NO2 OH CH2OH (d) (s) Metamers CH3 43. Find sum of stereoisomer of following compound. O Number of stereoisomers (a) CO2H HO ¾¾® (a) OH CH3OH (b) ¾¾® (b) HO (c) HOCH2–CH–CH–CH–CH–CH2–CH–CH–CH–CH–CH2–OH ¾¾®(c) CH2–OH OH OH O O OH (d) HO ¾¾® (d) OH OH https://t.me/studyzee

144 OH O 44. OH HO H OH 1 Prostaglandin E1 Prostaglandin E 1 1 is a compound produced by the body to regulate a variety of processes including blood clotting, fever, pain and inflammation. A. Which of the following functional groups is not contained in 1 ? (a) A ketone (b) An alcohol (c) A carboxylic acid (d) An alkene (e) A nitrile B. How many asymmetric (stereogenic) centres are present in compound 1? (a) 3 (b) 4 (c) 5 (d) 6 C. How many sp 2 hybridised carbon atoms are present in compound 1 ? (a) 1 (b) 2 (c) 3 (d) 4 D. What is the geometric configuration about the double bond in compound 1? (a) E (b) Z H3C OH H H 45. HH HO Ethynylestradiol (1) The synthetic steroid ethynylestradiol (1) is a compound used in the birth control pill. A. How many sp 3 hybridised carbon atoms are present in compound (1)? (a) 8 (b) 9 (c) 10 (d) 11 (e) 12 B. How many sp 2 hybridised carbon atoms are present in compound (1) ? (a) 4 (b) 5 (c) 6 (d) 7 (e) 8 C. How many sp hybridised carbon atoms are present in compound (1) ? (a) 2 (b) 4 (c) 6 (d) 8 (e) 10 D. Which of the following functional group is contained in compound (1) ? (a) A ketone (b) An alcohol (c) A carboxylic acid (d) An ester E. How many asymmetric (stereogenic) centres are present in compound (1) ? (a) 2 (b) 3 (c) 4 (d) 5 https://t.me/studyzee

46. Match the column. 145 Column (I) Column (II) (a) C2-axis of symmetry (p) (b) C3-axis of symmetry (q) CH3 (c) Plane of symmetry H3C (d) Centre of symmetry (r) H3C (s) https://t.me/studyzee

146 H3C (t) CH3 https://t.me/studyzee

147 Subjective Problems 1. Number of chiral isomers are: Cl Cl Cl Cl Cl H H (a) H Cl (b) H Br (c) H D (d) H H Br H CH3 Cl H HH CH3 (e) H Cl (f) Cl H (g) (h) H H Cl H Consider only a Cl conformation with Me group perpendicular to the aromatic ring H H CH3 CH3 CH3 Cl (i) H (j) (k) H O Cl CH2—OH 2. Cl Number of stereoisomer are 3. (i) H (ii) ¾H¾2 ® (D) C CH3 Ni (Major) CH3 (C) Sum of number of stereoisomer (C) Degree of unsaturations in (D). 4. How many 5 membered parent chain alkane are possible for C7H16? 5. Theoretical possible geometrical isomer of https://t.me/studyzee

148 6. Total number of possible structural isomers of C 5H11Br. 7. Total number of plane of symmetry present in given compound is Cl Cl Cl Cl 8. Total number of isomers for C 4H 6Br2 containing cyclobutane ring are ( including stereoisomer) ? 9. Total number of structural isomers of C 9H18 containing cyclohexane ring. 10. How many structural isomer are possible for C 4H10O (only alcohol). 11. Number of structural isomer of C 6H14 is . CH2—Cl 12. (a) ¾¾® (x) ( Number of plane of symmetry) CH2—Cl (b) ¾¾® (y) ( Number of mesoisomer of 1, 2-dichlorocyclopentane) Cl Cl Sum of (x+y=?) 13. Find out the total number of stereocentre in the given compound. CH3—CH==CH—CH—CH—CH3 Br Cl 14. Find out the total number of stereoisomers of the given following compound. Cl Cl—CH==CH—C—CH == CH—Cl H 15. Find the total number of isomers of C7H14 (only 5-membered ring). 16. x = number of compounds which undergoes Tautomerisation to form an Aromatic product. OO OO (a) (b) (c) (d) N HO https://t.me/studyzee

O O 149 (e) O O (h) (f) (g) N—O—H 17. If molecule is pyramidal, X stereoisomers are possible for : C abed find the value of X. https://t.me/studyzee