MS CHAUHAN ADVANCE

550 151. What is the product of the following reaction ? CH3 OCH3 + C == CH2 H2SO4 CH3 OCH3 (b) (CH3)2CH OCH3 (a) CHCH2 OCH3 CH3 OCH3 | (c) CHCH2 (d) (CH3)2CH 152. Which sequence represents the best synthesis of 4-isopropylbenzonitrile ? (CH3)2CH C ºº N 4-Isopropylbenzonitrile (a) 1. Benzene + (CH 3 )2 CHCl, AlCl 3; 2. Br2 ,FeBr3 ; 3. KCN (b) 1. Benzene + (CH 3 )2 CHCl, AlCl 3; 2. Fe, HCl,; 5. HNO 3 ,H 2SO 4; 3. 4. NaOH Fe, HCl ; NaNO 2 , HCl, H 2O 3. Fe, HCl; (c) 1. Benzene +(CH 3 )2 CHCl, AlCl 3; 2. HNO 3, H 2SO 4 ; 3. 4. NaNO 2 HCl 5. 2. KCN (d) 1. Benzene + HNO 3 ,H 2SO 4 ; 5. 4. NaNO 2 ,HCl,H 2O; (CH 3 )2 CHCl, AlCl 3; CuCN CH3 153. Br 1. Mg Ether ¾2¾. H¾3O¾+ ¾¾¾® A, Product A is : 3. KMnO4 OH- 4. H+ COOH OH OH CH3 (a) (b) COOH (c) (d) https://t.me/studyzee

551 154. 1. 2¾A.irN,¾VH23O¾,¾D5, ®D A, Product A is : (a) ¾ 3. KOBr, D CO COOH NH (b) NH2 CO O COOH C (c) (d) CONH2 NH 155. What is correct order of rate of nitration of the following compounds ? + C 6H 5CH 3 C 6H 6 C 6D 6 C 6T6 C 6H 5Br3 C 6H 5 N R 3 C 6H 5NMe 2 A B CD E F G (a) G > A > B > C > D > E > F (b) G > B > C > D > A > F (c) G > A > B = C = D > E > F (d) G > A > B > C = D > E > F 156. COCl ¾A¾lC¾l3 ®[X ] ¾N¾a—¾exHc¾egs,sH¾¾Cl ®[Y ] ; Product Y is : | + COCl (a) (b) (c) (d) 157. Compound A (C7H 8O) is insoluble in water, dilute HCl & aqueous NaHCO 3, but it dissolves in dilute NaOH. When A is treated with Br2 water it is converted into a compound C7H 5OBr3 rapidly. The structure of A is : OCH3 OH OH OH CH3 (a) (b) (c) (d) CH3 CH3 https://t.me/studyzee

552 158. Give the product of the following reaction sequence : CO2H 1. HNO3 H2SO4 CO2H OH ¾2¾. H¾2 P¾d C¾¾® Product 3. NaNO2 HCl 4. CuCN 5. MeMgBr 6. H3O+ O (a) (b) (c) (d) 159. Give the product of the following reaction sequence: 1. HNO3 H2SO4 Product ¾23¾.. BH¾r22 PF¾deBC¾r3¾® 4.Cl2 FeBr3 5. NaNO2 HCl 6. KI Cl I I Br Br Br Cl Cl Cl (a) (b) (c) (d) I Br I 160. Which represents an intermediate formed in the reaction of toluene and chlorine at elevated temperature in sunlight ? H CH3 H CH3 (a) (b) Cl Cl (c) CH2 (d) CH2 161. The decreasing order of reactivity of m-nitrobromobenzene (I), 2, 4, 6- trinitrobromo-benzene (II), p-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV), towards OH -ions is : (a) I > II > III > IV (b) II > IV > III > I (c) IV > II > III > I (d) II > IV > I > III 162. Which one of the following compounds is most reactive for ArSN2 reaction ? Cl Cl Cl Cl (a) (b) NO2 (c) NO2 NO2 (d) NO2 NO2 https://t.me/studyzee

553 163. Which one amongst the following carbocations is most stable ? Å (b) (a) C 6H 5 — C H — C 6H 5 Å C (d) (c) CH 3 — C — CH 3 | CH3 164. Cyclopentadiene is much more acidic than cyclopentane. The reason is that : (a) cyclopentadiene has conjugated double bonds (b) cyclopentadiene has both sp 2 and sp 3 hybridized carbon atoms (c) cyclopentadiene is a strain-free cyclic system (d) cyclopentadienide ion, the conjugate base of cyclopentadiene, is an aromatic species and hence has higher stability COCH3 COCH3 COCH3 COCH3 165. CH3O H3C O2N Me2N (I) (II) (III) (IV) Friedel-Crafts acylation reaction can be used to obtain the compounds (a) II, III and IV (b) I, III and IV (c) I and II (d) II and III 166. The major product of the reaction is : Br2 Product FeBr3 (a) Br (b) (c) (d) Br Br Br https://t.me/studyzee

554 167. The decreasing order of reactivity of given compound towards nucleophilic substitution with aqueous NaOH is : Br Br Br Br O2N NO2 NO2 NO2 NO2 NO2 NO2 (I) (II) (III) (IV) (a) I > II > III > IV (b) II > IV > III > I (c) IV > II > III > I (d) II > IV > I > III 168. Identify the end product (B) of the following sequence of reactions. OH ¾c¾on¾c. H¾2S¾O¾4 ® A ¾B¾r2¾H2¾O ® B 100°C (excess) OH OH OH OH Br Br Br Br Br SO3H Br (a) (b) (c) (d) Br SO3H Br Br 169. Consider the following sequence of reactions : COOH ¾S¾OC¾¾l2 ® A ¾1¾. A¾lC¾l3 ® B Zn— Hg ¾¾¾¾¾¾® C CH2C6H5 2. H3O+ conc. HCl, heat The end product (C) is : O (a) O (b) O C6H5 C6H5 O (c) (d) https://t.me/studyzee

555 170. For the diazonium ions the order of reactivity towards diazo-coupling with phenol in the presence of dilute NaOH is : Me2N N2+ O2N N2+ CH3O N2+ CH3 N2+ (I) (II) (III) (IV) (a) I < IV < II < III (b) I < III < IV < II (c) III < I < II < IV (d) III < I < IV < II 171. Major product obtained in given reaction is : + ¾H¾2S¾O¾4 ® (2 mole) (a) (b) (c) (d) 172. ¾H¾¾Å ® (B) ; (A) & (B) are isomers. Product (B) is : (A) or AlCl3 (major) Dewar's Benzene (a) (b) (c) (d) https://t.me/studyzee

556 173. The step shown below is a recent synthesis of corannulene. ¾ P¾d¾C ® ( A) C 20H10 (D) Corannulene Product (A) is : (a) (b) (c) (d) a 174. c 175. d 176. b Identify the position where E.A.S. will take place : (a) a (b) b (c) c (d) all the position are identical 14 CH2 — CO2H ¾(¾1) ¾KM¾nO¾4, H¾O-¾,¾D ® (2) H3OÅ The labelled carbon goes with : 14 14 14 14 (a) Ph — CO 2H (b) CO2 (c) Ph — CH 2 — CO 2H (d) CH 4 What is the expected order of reactivity of the following compounds in electrophilic chlorination (Cl 2 + FeCl 3 ) ? (more reactive > less reactive) I II III IV https://t.me/studyzee

557 (a) I > II > III > IV (b) IV > III > II > I (c) III > I > IV > II (d) II > III > I > IV 177. Which of the following is the major product from sulfonation of a-tetralone ? O SO3H O H2SO4 O (a) heat HO3S (b) OO (c) (d) HO3S SO3H 178. Which of the following procedures would be best for the preparation of phenyl benzyl ether ? C 6H 5OCH 2C 6H 5 (b) C 6H 5O(-)Na(+) + C 6H 5CH 2Cl (a) C 6H 5Cl + C 6H 5CH 2O(-)Na(+) (c) 2C 6H 5Cl + Na 2O (d) 2C 6H 5MgBr + CH 2O 179. Which of the following procedures would be best for achieving the following reaction ? CH3 CH2–Cºº CH3–CH3 ? Br Br (a) (i) KOH and heat (ii) CH 3C ºº C — Br (b) (i) KMnO 4 and heat (ii) CH 3C ºº C(-)Na(+)(iii) excess H 2O (c) (i) NBS in CCl 4 and heat (ii) CH 3C ºº C(-)Na(+) (d) (i) Mg in ether (ii) CH 3C ºº CBr (iii) excess H 3PO 4 180. Which of the following procedures would be best for achieving the following reaction ? CH3 O2N CO2H ? Cl Cl Br (a) (i) Br2 + FeBr3 (ii) KMnO 4 and heat (iii) HNO 3 and H 2SO 4 (b) (i) KMnO 4 and heat (ii) Br2 + FeBr3 (iii) HNO 3 and H 2SO 4 (c) (i) NBS in CCl 4 and heat (ii) KMnO 4 and heat (iii) HNO 3 and H 2SO 4 (d) (i) NBS in CCl 4 and heat (ii) NaNO 2 and heat https://t.me/studyzee

558 181. Phenol reacts with acetone in the presence of conc. sulphuric acid to form a C15H16O 2 product. Which of the following compounds is this product ? O–C6H5 (b) HO OH (a) O–C6H5 O O (c) (d) C6H5 O C6H5 182. O 183. Heating benzene in a large excess of 80% D 2SO 4 in D 2O results in what product ? 184. (a) C 6H 5SO 3D (b) C 6H 5OD (c) C 6H 5D (d) C 6D 6 A solution of cyclohexene in benzene is stirred at 0°C while concentrated sulphuric acid is added. After washing away the acid and removing the excess benzene, what product is isolated? (a) cyclohexylbenzene (b) 1-cyclohexylcyclohexene (c) trans-1,2-diphenylcyclohexane (d) 1,1-diphenylcyclohexane Indentify the reagents S and m in the scheme below in which R is converted to the nitrite V via the benzylic halide T. CH2 — Br CH2 —CN ¾(¾m¾) ® (R) ¾(¾¾S) ® O S O R, S and m respectively are : m R (a) Cl H — C — (AlCl 3 ) HCN O CH2Br (b) Cl —C — (AlCl 3 ) HCN O CH2Br (c) Cl —C — (AlCl 3 ) KCN KCN (d) — C —Cl O CH2Br CH2Br (AlCl 3 ) O https://t.me/studyzee

559 185. Two aromatic compounds P and Q give product R. P + Q ¾R¾ea¾gen¾t(¾s) ® Reactant P, Q and reagent used in above reaction are : PQ Reagent AlCl 3 (a) — C — Cl CH3 AlCl 3 O AlCl 3 (b) —C—H Cl CH3 ZnCl 2 O CH3 (c) C ==O Cl O (d) Cl — C CH3 186. Which of the following C 6H 6 compounds has a single set of structurally equivalent hydrogen atoms ? H — C ºº C — C H 2 — C H 2 — C ºº C — H I II III IV V (a) I and II (b) I and IV (c) I and V (d) I, II and III 187. Which of the following compounds would not be considered aromatic in its behaviour? (a) (b) (c) (d) N N 188. A C 8H10 hydrocarbon is nitrated by HNO 3 and sulphuric acid. Two, and only two, C 8H 9NO 2 isomers are obtained. Which of the following fits this evidence ? (a) ethyl benzene (b) ortho-xylene (c) meta-xylene (d) para-xylene 189. Which of the following benzene ring substituents is deactivating but ortho-para directing ? (a) —N == O (b) — OCH 3 (c) — COCH 3 (d) — NO 2 https://t.me/studyzee

560 190. Which of the following compounds forms ortho- benzenedicarboxylic acid when oxidized by hot aqueous potassium permanganate ? (a) (b) (c) (d) 191. Which of the following organic chlorides will not give a Friedel-Craft alkylation product 192. when heated with benzene and AlCl 3? (a) (CH 3 )3 CCl (b) CH 2 == CHCH 2Cl (c) CH 3CH 2Cl (d) CH 2 == CHCl Which of the following is aromatic ? Q .. Å .. (a) (b) (c) (d) (carbene) (carbene) 193. Which of the following substance will increase the acidity of phenol ? (a) Dil. H 2SO 4 (b) Dil. HCl (c) Conc. H 2SO 4 (d) Conc. CH 3COOH 194. + PhMgBr ¾® E + F N | H Pyrrole E + MeCl ¾® G + H F + MeCl ¾® no reaction without a catalyst N N N Ph H Ph MgBr 2 3 H 1 4 Ph Me N N Me N HH H 56 7 The structure of products E – H, respectively are (a) 3, 2, 6, 7 (b) 4, 5, 6, 1 (c) 3, 4, 5, 2 (d) 3, 2, 4, 5 O 195. ¾H¾¾+ ® (A); Product A is : https://t.me/studyzee

561 O OH (a) (b) O (c) (d) none of these O 196. H+ RR OH Identify the product of the above rearrangement reaction. OOO (a) (b) (c) (d) R RR R RR RR 197. Product obtained in the following transformation is : O ¾P¾P¾A ® PPA = polyphosphoric acid Ph O Ph (b) (a) Ph O (c) O (d) 198. The compound X in the reaction. anhydrous AlCl3 X Ph + ICl I Cl (d) Cl I Cl (a) (b) (c) I https://t.me/studyzee

562 OH OH Br Br 199. + 3Br2 +3HBr Br (b) Nucleophilic substitution (a) Nucleophilic addition (d) Electrophilic substitution (c) Electrophilic addition (e) Free radical substitution CH3 CH2Br 200. +Br2 +HBr (a) Nucleophilic addition (b) Nucleophilic substitution (d) Electrophilic substitution (c) Electrophilic addition (e) Free radical substitution Cl 2/hv (P) 201. Cl2 /AlCl3 (Q) Identify major product of both respectively. CH2—Cl Cl (a) (b) Cl Cl Cl Cl (c) (d) Cl Cl Cl OH OH 202. + Ph — N + Cl - ¾p¾H=¾=1¾0-1¾1 ® 2 Characteristics of above reaction is : N==N—Ph (a) C — N coupling reaction ; Carbocation is intermediate (b) N — N coupling reaction ; Carbocation is intermediate (c) C — N coupling reaction ; Carbanion is intermediate (d) N — N coupling reaction ; Carbanion is intermediate https://t.me/studyzee

563 203. The compound formed on heating chlorobenzene with chloral in the presence of 204. concentrated sulphuric acid, is : (a) Freon (b) DDT (c) Gammexene (d) Hexachloroethane Predict the product of the following reaction. O 1. /AlCl3 Cl 2. Zn(Hg), HCl 3. Br2, FeBr3 OO Ac2O (a) (b) Br Br O (c) (d) Br Br 205. Predict the major product of the following reaction sequence. ¾C¾l2 ¾AlC¾¾l3 ® A ¾12¾.. FNe¾a,OHH¾Cl ® B C ¾B¾r2¾Fe¾B¾r3 ® D ¾N¾aO¾¾H ® E NO2 ¾H¾2S¾OH4¾,2NOa¾NO¾2 ® F ¾H¾H3P2¾OO¾2 ® G (a) Cl Br Cl Br Cl Br (b) (c) (d) Cl Br 206. Give the major product of the following reaction : O O O NHPh ¾C¾H3¾Cl,¾AlC¾¾l3 ® (a) O O H3C NHPh (b) NHPh CH3 https://t.me/studyzee

564 NHCOPh NHCOPh (d) (c) H3C CH3 CH3 207. ¾B¾F¾re2 ®( A) ¾S¾n ¾H¾Cl ®(B) ¾N¾aN¾O2¾+H¾¾Cl ®(C) ¾H¾3P¾O¾2 ®(D) ¾K¾HMO¾nOs¾4 ®(E) NO2 CO2H CO2H CO2H Product (E) is : Br (d) (b) CO2H Br (c) CO2H (a) 208. Br A O B ; Products; H+, D F NO2 NH2–NH2 NO2 Incorrect statements regarding above reaction is 209. (a) Product A is 2, 4-DNP 210. (b) A to B dehydration reaction (c) A to B, geometrical isomersm will obtained as a product (d) B is known as oxime (i) chlorobenzene is mono-nitrated to M (ii) nitrobenezene is mono-chlorinated to N (iii) anisole is mono-nitrated to P (iv) 2-nitrochlorobenzene is mono-nitrated to Q. Out of M, N, P and Q the compound that undergoes reaction with aq. NaOH fastest is (a) M (b) N (c) P (d) Q For the transformation the reagent used is Br Br NÅ 2 Cl2 (a) LiAIH 4 (b) H 3PO 2 (c) H 3O + (d) H 2 / Pt https://t.me/studyzee

565 211. The reaction OH OH CHO + CHCl3 NaOH/Heat H+ is known as (a) Perkin reaction (b) Sandmeyer reaction (c) Reimer-Tiemann reaction (d) Cannizzaro reaction 212. A compound X formed after heating coke with lime react with water to give Y which on passing over redhot iron at 873 produces Z. The compound Z is (a) (b) (c) (d) 213. The reaction of 50% aq KOH on an equimolar mixture of 4-methylbenzaldehyde and formaldehyde followed by acidification gives : OH 214. + HCOOH 215. OH (a) OH H3C (b) H3C CHO COOH (c) +CH3OH (d) H3C OH Which isomer of xylene can give three different monochloroderivatives ? (a) o-xylene (b) m-xylene (c) p-xylene (d) xylene cannot give a monochloro derivative CH3 CH3 CH3 DD D (I) (II) (III) The rate of o-nitration of the above compounds, (I) toluene, (II) 2-D-toluene and (III) 2, 6- D 2-toluene is in the following order (a) I > II > III (b) II > I > III (c) III > I > II (d) The rate is the same for all the three compounds 216. Cyclooctatetraene is expected to have : 217. (a) a planar structure (b) a tub-shaped structure (c) open chain isomeric structure (d) tatutomeric bicyclic structure 3HC red hot ( A) ¾C¾H¾3CO¾Cl® (B) ¾N¾i /¾H 2® C + D ºº CH ¾¾¾® Fe AlCl3 25°C Relation between C and D. (a) ldentical (b) enantiomer (c) diastereomer (d) position https://t.me/studyzee

566 ANSWERS — LEVEL 1 1. (b) 2. (d) 3. (b) 4. (c) 5. (a) 6. (b) 7. (c) 8. (b) 9. (d) 10. (d) 11. (a) 12. (a) 13. (a) 14. (a) 15. (a) 16. (b) 17. (b) 18. (a) 19. (b) 20. (b) 21. (c) 22. (c) 23. (b) 24. (b) 25. (d) 26. (c) 27. (c) 28. (b) 29. (b) 30. (b) 31. (b) 32. (a) 33. (b) 34. (d) 35. (c) 36. (c) 37. (a) 38. (c) 39. (a) 40. (b) 41. (b) 42. (c) 43. (c) 44. (b) 45. (c) 46. (b) 47. (b) 48. (b) 49. (b) 50. (b) 51. (b) 52. (a) 53. (c) 54. (c) 55. (a) 56. (a) 57. (d) 58. (b) 59. (b) 60. (b) 61. (c) 62. (b) 63. (b) 64. (b) 65. (a) 66. (a) 67. (c) 68. (b) 69. (a) 70. (d) 71. (b) 72. (a) 73. (a) 74. (c) 75. (a) 76. (d) 77. (c) 78. (b) 79. (c) 80. (b) 81. (b) 82. (c) 83. (a) 84. (c) 85. (d) 86. (b) 87. (d) 88. (b) 89. (d) 90. (d) 91. (d) 92. (d) 93. (d) 94. (b) 95. (c) 96. (d) 97. (b) 98. (d) 99. (b) 100. (b) 101. (b) 102. (c) 103. (d) 104. (a) 105. (b) 106. (d) 107. (c) 108. (c) 109. (b) 110. (b) 111. (c) 112. (b) 113. (c) 114. (a) 115. (b) 116. (b) 117. (a) 118. (b) 119. (b) 120. (c) 121. (b) 122. (b) 123. (c) 124. (b) 125. (b) 126. (b) 127. (c) 128. (c) 129. (c) 130. (b) 131. (d) 132. (b) 133. (b) 134. (a) 135. (b) 136. (a) 137. (b) 138. (c) 139. (d) 140. (b) 141. (b) 142. (c) 143. (a) 144. (b) 145. (b) 146. (c) 147. (a) 148. (c) 149. (c) 150. (b) 151. (d) 152. (c) 153. (c) 154. (b) 155. (c) 156. (c) 157. (c) 158. (b) 159. (c) 160. (c) 161. (b) 162. (c) 163. (d) 164. (d) 165. (c) 166. (c) 167. (b) 168. (d) 169. (d) 170. (b) 171. (b) 172. (a) 173. (a) 174. (b) 175. (b) 176. (d) 177. (b) 178. (b) 179. (c) 180. (a) 181. (b) 182. (d) 183. (a) 184. (c) 185. (c) 186. (b) 187. (b) 188. (b) 189. (a) 190. (b) 191. (d) 192. (b) 193. (c) 194. (a) 195. (c) 196. (b) 197. (b) 198 (b) 199 (d) 200 (e) 201. (c) 202. (c) 203. (b) 204. (c) 205. (a) 206. (c) 207. (c) 208. (d) 209. (d) 210. (a) 211. (c) 212. (a) 213. (b) 214 (b) 215. (d) 216. (b) 217. (b) https://t.me/studyzee

567 Level - 2 1. Each of the six compounds shown at the bottom of the page has two aromatic (benzene) rings. In each case the two rings are different and are labeled A & B. If an electrophilic substitution, such as nitration or bromination, is carried out on each compound, then identify which ring (A or B) will be preferentially attacked, and indicate the orientation of the substitution (ortho/para, meta or all sites). Compound Reactivity Substitution Compound Reactivity Substitution A ortho/para A ortho/para 1. B meta 2. B meta all sites all sites A ortho/para A ortho/para 3. B meta 4. B meta all sites all sites A ortho/para A ortho/para 5. B meta 6. B meta all sites all sites Compound Compound|||| || |CH3 B OB 1. 2. N S A OO A OB 4. CH3 O 3. A O 6. N B O C|H3 B A 5. N N O A CH3 O O CH3 || CH3 A B https://t.me/studyzee

568 2. When given substituents on a benzene ring, as activating or de-activating and as ortho-para or meta directing for elctrophilic aromatic substitution fill the following by appropriate () right or (#) wrong. Substituent Activating De-activating Ortho/para Meta 1. — OCH 3 O 2. || — C — O — CH 3 —O — C — CH 3 3. || O 4. — CH 3 5. — F 6. — Ph O 7. || — NH — C — CH 3 O 8. || — C — NH — CH 3 9. — Br 10. — CN 11. — CF3 O 12. || — C— NH 2 O 13. || — C — OH 14. — CH == CH 2 https://t.me/studyzee

569 O 15. || -CH = CH - C - OH O 16. || -CH = CH - C - H 17. – S – Et - S - Et 18. || O O || 19. - S - Et || O 20. – N = O 21. - CH 2X 22. - CHX 2 3. Devise a series of reactions to convert benzene into meta-chlorobromobenzene. Select reagents and conditions from the following table, listing them in the order of use. Compound Compound Compound 1. sulphuric acid (conc.) 5. Mg in ether 9. Cu 2Br2 + HBr heat 6. PBr3 10. (CH 3CO)2O + Pyridine 2. Cl 2 + FeCl 3 and heat 7. H 3PO 2 3. NaNO 2 + H 3O(+ ) 0°C HNO 3(conc.)+ 4. H 2 8. H 2SO 4 (conc.) and heat Pt catalyst (a) 1 then 2 then 6 (b) 2 then 8 then 4 then 3 then 9 (c) 8 then 4 then 10 then 2 then 3 then 9 (d) 8 then 2 then 4 then 3 then 9 https://t.me/studyzee

570 4. Match the Column (I) and Column (II). (Matrix) Column (I) Column (II) Cl C Aromatic (a) N N (p) Cl C N C — Cl H N H—B B—H (b) (q) (4n + 2)p electron in a single ring N N—H HB H (c) Fe(C 5H 5)2 (r) 4np electron in a single ring (d) Cr(C 6H 6 )2 (s) Effective atomic number of metal = 36 5. Match the Column (I) and Column (II). Column (II) Column (I) Number of p - electron Compound (Monocyclic) 2pe 6pe (a) C 4H -2 (p) 8pe 4 10 pe (b) C 4H +2 (q) 4 (c) C 9 H +1 (r) 9 (d) C 9 H -1 (s) 9 https://t.me/studyzee

571 6. Match the Column (I), Column (II) and Column (III). (Matrix) Column I Column II Column III (a) (p) Aromatic (w) (4n + 2)p electron. n = 0,1,2,3 (b) (q) Non-aromatic (x) 4np electron n = 1,2,3 (c) (r) Anti- aromatic (y) Non-planar compound (d) (s) Planar compound (z) Readily reacts with active metal 7. Match the Column (I), Column (II) and Column (III). (Matrix) Column I Column II Column III (a) (p) Readily react with (w) Aromatic active metal Readily undergo (b) (q) Dimerization at room (x) Anti-aromatic temperature (c) –2 (r) (4n + 2)p electron (y) Non-aromatic n = 0,1,2,3 (d) +2 (s) 4np electron (z) High dipole https://t.me/studyzee

572 8. Among the following compound. Compound Compound Compound (a) (b) N (c) NN (d) (e) (f) N (i) C 8H -2 OH 8 + (g) (h) C 3H + 3 N (l) (j) (k) NN N (a) Number of compounds which are aromatic = P (b) Number of compounds which are anti-aromatic = Q (c) Number of compounds which are non-aromatic = R (d) Number of compounds which readily undergo dimerization at room temperature = S (e) Number of compound which reacts with active metal = T Sum of P + Q + R + S + T = 9. Of the following compounds which will react with Br2 at room temperature in dark. (a) Benzene (C 6H 6 ) (b) Cyclohexene (C 6H10 ) (c) Cyclohexane (C 6H12) (d) Propanoic Acid (C 2H 5CO 2H) (e) Phenol (C 6H 5OH) (f) Nitrobenzene (C 6H 5NO 2) (g) Hexyne (C 6H10 ) (h) 2,2-dichloropropane (C 3H 6Cl 2) https://t.me/studyzee

10. Among the following compound. 573 Compound Compound Compound (a) (b) C 8 H -2 (c) 8 N (d) (e) (f) N (g) N (i) C 3H +1 (h) 3 NN OH (l) (j) (k) N (a) Number of compounds which are aromatic = w (b) Number of compounds which are non-aromatic = x (c) Number of compounds which are anti-aromatic = y (d) Number of compounds which readily undergo Dimerization at room temperature = z Sum of w + x + y + z = ... https://t.me/studyzee

574 11. Complete the following table. Reactant Reagents(s)/Conditions Major Organic Products CH2Cl CH3 (a) (A) NH2 1. NaNO 2 in dilute (B) (b) H 2SO 4 0 – 5° C (C) NO2 2. heat or boiling CH3 OH OH (c) SO 3 conc. H 2SO 4 and (d) (D) 1. NaOH heated at 330°C CH3 2. dilute H 3O + Cl CH3 NO2 1. aqueous NaOH heated at 60°C (E) (e) NO2 2. dilute H 3O + https://t.me/studyzee

575 12. Comprehension Given is the energy profile diagram of nitration of benzene using mixed acid. (HNO3 + H 2SO4 ). T.S1 P.E. T.S2 (x) Ph – NO2 C6H6 + NO2 reaction-co-ordinate , A. Identify (x) in above reaction : NO2 d+NO2 H NO2 H d+ (d) None (a) (b) d+ (c) d+ B. Identify T.S1 in the above reaction. NO2 d+NO2 H NO2 H d+ (c) d+ (a) (b) d+ (d) None C. Identify T.S2 in the above reaction : NO2 d+NO2 H NO2 H d+ (c) d+ (a) (b) d+ (d) None https://t.me/studyzee

576 13. Examine the ten structural formulas shown below and select those that satisfy each of the following conditions. Enter one or more letters (a through j) in each answer box, reflecting your choice for each. Compound Compound CH3 N(CH3)2 a. b. SO3H NO2 c. d. OCH3 H | e. f. N O C|H3 C|H3 g. N – CH3 h. C – CH3 | | CH3 Br– CH3 O Br i. j. A. Which compounds undergo electrophilic nitration more rapidly than benzene ? B. Which compounds give meta substitution under electrophilic bromination conditions ? https://t.me/studyzee

577 14. Nitrobenzene is a versatile compound that may be converted into a wide variety of substituted benzenes. Five such synthesis are shown below. In each reaction box above an arrow write letters designating the reagents and conditions, selected from the list at the bottom of the page, that would effect the transformation. The reagents must be written in the answer box in the correct order of their use. You may assume appropriate heating or cooling takes place, and more than one equivalent of the reagent may be used if needed. Reactant Reagent Product Br a. ¾¾¾¾® v. b. ¾¾¾¾® w. Cl CN NO2 c. ¾¾¾¾® x. O2N nitrobenzene CH3 N N O CH3 Cl NH2 d. ¾¾¾¾® y. NH2 Cl NH2 e. ¾¾¾¾® z. H2N Cl Reagents Reagents A. H 2, Ni catalyst F. Cl 2 & FeCl 3 B. KBr & Cu 2Br2 G. NaOH 10% solution C. KCN & Cu 2(CN)2 H. (CH 3CO)2O, pyridine D. HNO 2 0° C I. HNO 3 H 2SO 4 E. CH 3I & pyridine https://t.me/studyzee

578 15. Match the column I and II. Column (I) Column (II) Group Effect on phenyl ring (p) o/p-directors (a) -CH = CH - CO 2H (q) meta-directors O (r) Activating group (b) || (s) De-activating group -O - S - CH 3 O Column (II) Effect on phenyl group (c) || -NH - C - CH 3 (p) Activating group - S - CH 3 || (d) O 16. Match the column I and II. Column (I) Group NO (a) (b) (q) De-activating group https://t.me/studyzee

O–CH=CH2 579 (c) (r) o/p-director (s) meta-director S–Et (d) 17. Comprehension Nucleophilic Aromatic substitution (SN Ar ) : A substituted benzene derivative containing- NO 2 and Cl group at p-position is subjected to Nu-substitution. Cl OCH3 + CH 3ONa ¾C¾H3¾O¾H ® + NaCl 85°C NO2 NO2 p-chloronitrobenzene (p-Nitroanisole) (92%) A. Match the column I and II : X OCH3 ¾C¾H3¾DON¾a ® NO2 NO2 Column (II) Column (I) relative reactivity toward (SN Ar ). (a) X = halogen (p) 312 (b) (q) 1 (c) –F (r) 0.8 (d) – Cl (s) 0.6 – Br –I https://t.me/studyzee

580 B. If step-2 were rate determining step, which halogen of aryl halide is most reactive toward SN Ar . (b) Chloride (c) Bromide (D) Iodide (a) Fluoride C. Which of the following is most reactive toward SN Ar . Cl Cl NO2 (a) (b) NO2 NO2 Cl Cl O2N NO2 (d) (c) Cl NO2 NO2 D. ¾H¾NO¾¾3 ®( A) ¾C¾H3¾ON¾a ®(B) (Major) , product (B) is : Cl Cl OCH3 Cl Cl OCH3 (d) (a) (b) (c) OCH3 Cl NO2 NO2 NO2 OCH3 Cl Cl NO2 E. ¾(¾1) ¾NaO¾H,¾D ® (A) , Product (A) is : I (2) H3OÅ Br NO2 NO2 OH ON2 OH (a) OH (b) (c) I Br I Br (d) I OH Br https://t.me/studyzee

581 F. The cumulative effect of their fluorine activate the rings of penta and hexa fluorobenzene toward nucleophilic aromatic substitution. What is compound X in the following synthesis ? F F F F ¾H¾OC¾H2¾CH¾2O¾H ®( A) ¾K¾2C¾O¾3 ®( X) (C 8H 4F4O 2 ) F F NaOH, D D F (a) F F O – CH = CH2 F F O – CH2 – CHO OH H F F (b) (c) F F F O F F O F F O (d) CH3 F O F G. Which is the best route for the synthesis of CH3O NO2 Strating from benzen of ? NO2 (a) ¾B¾¾r2 ® ¾H¾NO¾¾3 ® ¾H¾NO¾¾3 ® ¾N¾aO¾CH¾3 ® FeBr3 H 2SO 4 H 2SO 4 CH 3OH (b) ¾H¾NO¾¾3 ® ¾H¾NO¾¾3 ® ¾B¾¾r2 ® ¾N¾aO¾CH¾3 ® H 2SO 4 H 2SO 4 FeBr3 CH 3OH (c) ¾H¾NO¾¾3 ® ¾B¾¾r2 ® ¾H¾NO¾¾3 ® ¾N¾aO¾CH¾3 ® H 2SO 4 FeBr3 H 2SO 4 CH 3OH (d) ¾H¾NO¾¾3 ® ¾B¾¾r2 ® ¾N¾aO¾CH¾3 ® ¾H¾NO¾¾3 ® H 2SO 4 FeBr3 CH 3OH H 2SO 4 18. Identify product (A) and write its structure. Ph ¾A¾HlC+¾l3 ® ( A) | Ph — CH | Ph https://t.me/studyzee

582 Subjective Problems 1. OH OH dil.HNO3 A+ B (1) Sn|HCl C (mild - basic (2) NaNO2/HCl condition) More Less D volatile volatile Double bond equivalent of D is : 2. How many isomers 'x' of C 8H10 when reacts with hot alkaline KMnO 4 give only aromatic dicarboxylic acid ? How many isomers 'y' of C 4H 8 when reacts with hot alkaline KMnO 4 give carbondioxide ? Sum of x+y=? 3. How many groups are o p director in the electrophilic aromatic substitution ? (i) —NH 2 (ii) —COH (iii) —N == O (iv) —COOH O (vii) —Et O (v) —OMe || || (ix) —N == NH 2 (vi) —O — C — Me (viii) — C — NH — Me (x) —SO 3H https://t.me/studyzee

ANSWERS — LEVEL 2 583 1. Meta Compound Reactivity Substitution # 1 B ortho/para  2 A ortho/para # 3 B ortho/para # 4 A all position # 5 B # 6 B meta # ortho/para  # 2. Activating De-activating Ortho/para  Substituent #  1. — OCH 3 O # # 2. || #  — C — O — CH 3 #  O #  #  3. || —O — C — CH 3 #  4. — CH 3 # # 5. — F #  # # 6. — Ph O 7. || — NH — C — CH 3 O 8. || — C — NH — CH 3 9. — Br 10. — CN https://t.me/studyzee

584 11. - CF3 #  # #  # O #  # 12. ||  # # #  # - C- NH 2 #  # O # 13. || # - C - OH # 14. - CH = CH 2 # # O # 15. || -CH = CH - C - OH O 16. || -CH = CH - C - H 17. – S – Et # - S - Et # 18. || O O # || 19. - S - Et || O 20. – N = O #  21. - CH 2X # 22. - CHX 2 # 3. d 4. a – p, q; b – p, q; c – p, q,s ; d – p, q, s 5. a – q; b – p; c – r; d – s 6. a – p, s – w; b – p, s – w; c – q – x, y, z; d – q – w – y 7. a – p, q, s – x; b – p – s – y; c – r – w, z; d – r – w, z 8. P + Q + R + S + T = 18 9. b, e 10. w + x + y + z = 14 https://t.me/studyzee

OH CH3 CH3 OH 585 NO2 11. A – Cl 2 hn or SO 2Cl 2 hn; B – ;C– ;D– ;E– NO2 SO3H Cl NO2 12. A – a; B – b; C – c 13. A – a, b, e, f, h; B – c, d, g, i (Note : yet C 6H 5Br is less reactive than C 6H 6 but o p directing) 14. v – F, A, D, B; w – A, H, I, G, D, C; x – A, E, D; y – F, I, A or I, F, A; z – A, H, I, F, G, A or A, H, I, F, A, G 15. a – p, s; b – p, r; c – p, r; d – p, s 16. a – p, r; b – p, r; c – p, r; d – p, r 17. A –a – p, b – q, c – r, d – s; B – d; C – d; D – a; E – b; F – c; G – a 18. Subjective Problems 3. 6 1. 9 2. 5 https://t.me/studyzee

586 13 PRACTICAL ORGANIC CHEMISTRY Level - 1 O O O ; Compounds (X) and (Y) can be differentiated by : 1. and OO (X) (Y) (a) H 3O Å , NaOI (b) H 3O Å , then Fehling test (c) H 3O Å , then Na (d) Both (b) and (c) OEt 2. Compound CH3 — CH and CH 3 – CH 2 – O – CH 2 – CH 3 can be differentiated by : ( Q) (P) (Acetal) OEt (a) H 3O Å , Na (b) H 3O Å , Tollens' test (c) H 3O Å , Fehling test (d) All of these NH2 NH2 3. and can be differentiated by : (aniline) (cyclohexyl amine) (a) Hinsberg test (b) Iso-cyanide test (d) NaOH (c) NaNO 2, HCl, then b-Naphthol https://t.me/studyzee

587 OH OCH3 OH 4. (p-ethyl phenol) (p-methyl anisole) (p-ethyl benzyl alcohol) Above compounds can be differentiated by using the reagent: (a) NaOH, Tollen's reagent, FeCl 3 (b) CrO 3, Tollen's reagent, FeCl 3 (c) Tollen's reagent, CrO 3 , FeCl 3 (d) Na, Tollen's reagent, FeCl 3 OO || OH O – C – CH3 OH CO2Et CO2Et O – C – CH3 CO2H CO2H 5. Salicyclic Ethyl Ethyl acetyl acid salicylate acetyl salicyclic acid Above compounds can be differentiated by the salicylate. Which of the following chemical test? (used in decreasing order) (a) NaOH, FeCl 3 ,NaHCO 3 (b) aq. NaHCO 3 ,FeCl 3 ,NaOH (c) NaOI, NaOH, NaHCO 3 (d) NaOH, Na, NaHCO 3 OH CO2H NH2 NO2 6. NO2 NO2 NO2 NO2 (m-nitrophenol) (m-nitro benzoic acid) (m-nitro aniline) (m-dinitro benzene) Above compounds can be differentiated by which of the following chemical test ? (used in decreasing order) (a) NaOH, NaHCO 3 , HCl (b) HCl, NaOH, NaHCO 3 (c) NaHCO 3 , NaOH, HCl (d) NaOH, HCl, NaHCO 3 CH2MgBr CH3 ¾¾NaIO2¾H ® CO2Na 7. ¾(¾i) C¾H3¾CH¾O ® (A) + CHI3, (ii)NH4Cl Product (A) in the above reaction is : CH3 CH3 OH CH2 – CH3 CH – CH3 (b) (a) OH CH3 O | (c) Ph — CH 2 —CH — CH 3 C – CH3 (d) https://t.me/studyzee

588 NH3Cl– NO2 8. and Cl (P) (Q) Above compounds (P) & (Q) can be differentiated by : (a) amm. AgNO 3 (b) NaOH (c) FeCl 3 (d) Both (a) & (b) 9. Which of following acid give positive Tollen's reagent test. (a) (CH2)2 CO2H CO2H CO 2H (d) HCO 2H (b) CH2 CO2H (c) | CO2H CO 2H 10. Which of following compounds give positive Tollen's test? O OCH3 O O OH O (d) (a) (b) (c) OCH3 OH 11. Give a simple test to differentiate cyclohexane and cyclohexene (a) Br2 H 2O (b) Bayer’s reagent (c) Tollen’s reagent (d) Both (a) and (b) 12. Give test to differentiate (Bromobenzene) Ph – Br and benzyl bromide (PhCH 2Br). (a) (i) aq. KOH (ii) Na (b) AgNO 3 (c) KMnO 4 (d) All these 13. Give test to differetiate 1,1-dichloroethane and 1, 2-dichloroethane : (a) 2,4 -DNP then aq. KOH (b) aq. KOH then 2, 4-DNP (c) NaHSO 3 (d) Lucas reagent 14. Test to differentiate between (CH 3OH) and (Ph – OH) is/are : (methanol) (Phenol) (a) Litmus test (b) FeCl 3 (c) Br2 H 2O (d) All of these 15. Acetaldehyde and benzaldehyde can be differentiated by : (a) Fehling test (b) Iodoform test (c) Tollen’s reagent (d) both (a) and (b) 16. Ethylamine and diethylamine cannot be differentiated by : (a) Hinsberg test (b) carbylamine test (c) Iodoform test (d) both (a) and (b) 17. Lassaigne’s test for the detection of nitrogen will fail in the case of : (a) NH 2CONH 2 (b) NH 2CONHNH 2.HCl (c) NH 2NH 2.HCl (d) C 6H 5NHNH 2. 2HCl https://t.me/studyzee

589 18. Sodium nitroprusside when added to an alkaline solution of sulphide ions produces a colouration which is : (a) red (b) blue (c) brown (d) purple 19. In Kjeldahl’s method, nitrogen present is estimated as : (a) N 2 (b) NH 3 (c) NO 2 (d) none of these 20. In Kjeldahl’s method of estimation of nitrogen, K 2SO 4 acts as : (a) an oxidising agent (b) catalytic agent (c) hydrolysing agent (d) boiling point elevator 21. The prussian blue colour obtained during the test of nitrogen by Lassaigne’s test is due to the formation of : (a) Fe[Fe(CN)6 ]3 (b) Na 3[Fe(CN)6 ] (c) Fe(CN)3 (d) Na 4[Fe(CN)5NOS] 22. A compound which does not give a positive test in Lassaigne’s test for nitrogen is: (a) urea (b) hydrazine (c) azobenzene (d) phenyl hydrazine 23. p-nitrophenol and o-nitrophenol are separated by : (a) distillation (b) steam distillation (c) crystallization (d) fractional crystallization 24. Which of the following reagent is used for the separation of acetaldehyde from acetophenone ? (a) NH 2OH (b) NaOI (c) Tollen's reagent (d) C 6H 5NHNH 2 25. The formula of gas is [CO]x . If its vapour density is 70, the value of x will be : (a) 2.5 (b) 3.0 (c) 5.0 (d) 6.0 26. The structure of the monomer that would give the following polymer by an addition mechanism is : CO2Me CO2Me (a) CO2Me CO2Me CO2Me (b) CO2Me (c) (d) CO2Me CO2Me 27. Identify the correct set of stereochemical relationships amongst the following monosaccharides I – IV OH OH OH OH O HO O O OMe HO O OMe (I) OH (II) OH (III) OH (IV) OH HO OMe OMe HO OH OH OH OH https://t.me/studyzee

590 (a) I and II are anomers ; III and IV are epimers (b) I and II are epimers ; III and IV are anomers (c) I and III are anomers ; I and II are epimers (d) I and III are epimers ; II and IV are anomers 28. A dye, phenolphtnalein is prepared by reacting phenol with phthalic anhydride in acidic medium. It give pink colour in alkaline medium due to extended conjugation in a new complex formed (phthalein - dye test) identify the complex A : O O s ¾O¾H®(A) Product ; The structure of (A) is: OH OH O Os Phenophthaline O Os (a) (b) OH OH O O O Os (c) (d) None O OH ANSWERS — LEVEL 1 1. (d) 2. (d) 3. (c) 4. (b) 5. (b) 6. (c) 7. (a) 8. (d) 9. (d) 10. (c) 11. (d) 12. (d) 13. (b) 14. (d) 15. (d) 16. (c) 17. (c) 18. (b) 19. (b) 20. (d) 21. (d) 22. (b) 23. (a) 24. (c) 25. (c) 26. (c) 27. (c) 28. (b) https://t.me/studyzee

591 Level - 2 1. Comprehension O CHO CO2H O–H O CH2 – CHO C – O – Et C – CH3 OCH3 CH3 O – CH = CH2 O – H OH (a) (b) (c) (d) (e) (f) A. Which isomer gives positive iodoform test ? (a) a (b) b (c) d (d) e B. Which isomer gives +ive Tollen’s test, also reacts with FeCl 3? (a) b (b) f (c) c (d) d C. Which isomer reacts with NaHCO 3 ? (b) d (a) c (d) f (c) e D. Which isomer on hydrolysis gives 1, 4-di hydroxybenzene ? (a) a (b) d (c) e (d) f O || 14 2. Ph — C — OH ¾¾NaH¾CO¾3 ® ( A) gas ; Ph — OH ¾¾N¾a ® (B)gas Sum of molecular mass of gas (A+B=?) ANSWERS — LEVEL 2 1. A – d; B – b; C – a; D – b 2. 48 https://t.me/studyzee

592 14 BIOMOLECULES Level - 1 1. Which statement correctly completes the statement ? Except for glycine, which is achiral, all the amino acids present in proteins ...... (a) are chiral, but racemic (b) have the L configuration at their a carbon (c) have the R configuration at their a carbon (d) have the S configuration at their a carbon 2. Assume that a particular amino acid has an isoelectric point of 6.0. In a solution at pH 1.0, which of the following species will predominate ? RR +| | (a) H 3NCH CO 2H (b) H 2NCH CO 2H RR +| – | – 3NCH 2 2 (c) H CO (d) H 2NCH CO 3. The pK a values for the three ionizable groups X, Y and Z of glutamic acid are 4.3, 9.7 and 2.2 respectively H O 2C — CH 2 —CH — CO 2 H X |Z +NH 3 The isoelectric point for the amino acid is : (a) 7.00 (b) 3.25 (c) 4.95 (d) 5.95 https://t.me/studyzee

593 R | 4. An amino acid may be represented by general formula H 2N – CH – COOH. If R = -CH 2C 6H 5 then it is phenylalanine (Phe) and if R = CH 3 then it is alanine (Ala). Find the sequence of reagents from those given below to synthesize Phe - Ala. CH 3 CH 3 | | (1) ZNHCHCO 2H (2) H 2NCHCO2CH 2C 6H 5 CH 2C 6H 5 CH 2C 6H 5 | | (3) ZNH CHCO 2H (4) H 2N CHCO 2CH 2C 6 H 5 (a) 1 and 2 (b) 1 and 4 (c) 2 and 3 (d) 3 and 4 5. Iso-electric point of alanine is (pH = 6). At which pH, maximum concentration of zwitter ion of alanine will be present ? (a) pH > 6 (b) pH < 6 (c) pH = 6 (d) pH = 7 O || 6. NH 2 – CH – C– NH – CH 2 – CO 2H | CH 3 Identify the amino acid obtained by hydrolysis of the above compound: (a) Glycine (b) Alanine (c) Both (a) and (b) (d) None of these 7. At iso-electric point : (a) conc. of cation is equal to conc of anion (b) Net charge is zero. (c) Maximum conc. of di-polar ion (Zwitter ion) will be present (d) All of the above 8. Which of following amino acid has lowest iso-electric point ? (a) Glycine (b) Alanine (c) Aspartic acid (d) Lysine 9. Find iso-electric point of given amino acid CH 3 — CH — CO 2H pK a = 2.2 | (a) 3.3 (b) 5.9 NH 3 (d) 11.8 Å pK b = 4.4 (c) 9.6 10. Find iso-electric point of the given amino acid O || H – O – C – CH 2 – CH 2 – CH – CO 2H (pK a = 2) | (pKa= 4) NH3 Å (pKa= 9) (a) 5.5 (b) 6.5 (c) 3 (d) 5 https://t.me/studyzee

594 11. H – C º C – H ¾¾Hg¾SO¾4 ®( A) (1) NH3 + HCN Product (B) of given reaction is : H2SO 4 ¾¾¾¾¾®( B); (2) H3O Å (a) Glycine (b) Alanine (c) valine (d) Leucine 12. Which amino acid does not contain chiral centre ? (a) Valine (b) Leucine (c) Glycine (d) Iso-leucine 13. Which of the following is Sanger reagent ? (a) 2,4-Di-nitro flurobenzene (b) Phenyl isocyanate (c) 2, 4-Di-nitro chlorobenzene (d) 2, 4-Di-nitro iodobenzene 14. A D-carbohydrate is : (a) Always dextrorotatory (b) Always laevorotatory (c) Always the mirror of the corresponding L-carbohydrate (d) None of these 15. Which L-sugar on oxidation gives an optically active dibasic acid (2 COOH groups) ? CHO CHO CHO CHO OH H H OH H OH H OH HO OH H (c) H OH (d) H H (a) HO H (b) HO OH H HO HH CH2OH HO CH2OH CH2OH CH2OH CH == N — NH — Ph C == N — NH — Ph 16. HO H The given osazone can be obtained by : H OH H OH CH2OH (a) D-glucose (b) D-mannose (c) D-Idose (d) Both (a) & (b) 17. Which of the following pair gives same phenyl osazone ? (a) D-Glucose and D-Allose (b) D-Glucose and D-Alfrose (c) D-Glucose and D-Mannose (d) D-Glucose and D-Talose 18. Which of the following is the Fischer projection of L-threonine (also known as (2S, 3R)- 2-amino-3-hydroxybutanoic acid) ? CO2H CO2H CO2H CO2H H NH2 (b) H2N H H NH2 (d) H2N H (a) H OH H OH (c) HO H HO H CH3 CH3 CH3 CH3 https://t.me/studyzee

595 19. Among the three compounds shown below, two yield the same product on reaction with warm HNO3. The exception is : CHO CHO CHO H HO H HO H HO H (c) HO OH OH (b) HO H (a) H H (d) None of these H OH H OH CH2OH CH3 CH2OH 20. The optical rotation of the a- form of a pyranose is + 150.7º, that of the b- form is + 52.8º. In solution an equilibrium mixture of these anomers has an optical rotation of + 80.2º. The percentage of the a-form in equilibrium mixture is : (a) 28% (b) 32 % (c) 68% (d) 72% 21. Which of the following represents the anomer of the compound shown ? HOCH2 O H H H H OH HO OH HOCH2 O H HOCH2 O OH (a) OH H (b) H H H OH H H H OH HO OH H O OH (c) OH HO H (d) None of these HOCH2 HH 22. Which set of terms correctly identifies the carbohydrate shown ? O CH2OH HH OH HO OH (1) Pentose (2) Pentulose (3) Hexulose (4) Hexose (5) Aldose (6) Ketose (a) 2, 6, 8 (7) Pyranose (8) Furanose (c) 1, 5, 8 (b) 2, 6, 7 (d) A set of terms other than these 23. For the complex conversion of D-glucose into the corresponding osazone, the minimum number of equivalents of phenyl hydrazine required is : (a) two (b) three (c) four (d) five 24. Which one of the following compounds will form an osazone derivative ? (a) CH 3CH 2COCH 2OH (b) CH 3COCH 2CH 2OH (c) CH 3CH 2CHOHCH 2OH (d) CH 3CH 2COCH 2OCH 3 https://t.me/studyzee

596 25. Which of the following structure is L-arabinose? HO CHO HO CHO H CHO HO CHO H H OH HO H (a) H OH (b) H OH (c) HO H H H OH HO H HO H (d) H H OH OH CH2OH CH2OH CH2OH CH2OH 26. Which one of the statements concerning the equilibrium shown is true ? HOCH2 H HOCH2 H O O HO H HO OH H OH H OH HO H HO H OH H (a) The two structures are enantiomers of each other. They have equal but opposite optical rotations and recemize slowly at room temperature (b) The two structures are enantiomers of each other. They racemize too rapidly at room temperature for their optical rotations to be measured (c) The two structures are diastereomers of each other. Their interconversion is called mutarotation (d) The two structures are diastereomers of each other. Their interconversion does not require breaking and making bonds, only a change in conformation 27. The configurations of the chirality centres in D-threose (shown) are : CHO HO H H OH (a) 2R, 3R (b) 2R, 3S CH2OH (d) 2S, 3S (c) 2S, 3R 28. Rapid interconversion of a-D-glucose and b-D-glucose in solution is known as : (a) racemization (b) asymmetric induction (c) fluxional isomerization (d) mutarotation 29. Identify the correct set of stereochemical relationships amongst the following monosaccharides I-IV. OH OH OH OH O OH O O OMe OH O OMe OH OH OH OH OH OMe OMe OH OH OH OH OH (I) (II) (III) (IV) (a) I and II are anomers ; III and IV are epimers (b) I and III are epimers ; II and IV are anomers (c) I and II are epimers ; III and IV are anomers (d) I and III are anomers ; I and II are epimers https://t.me/studyzee

597 30. What is the structure of L-glucose ? CHO CHO CHO HO H H OH H OH (c) HO H (a) H OH (b) HO H OH (d) None of these HO HH OH H H HO HO H H OH CH2OH CH2 – OH CH2 – OH H 31. What is the structure of L-glyceraldehyde? H–C=O (a) HO – CH2 OH (b) HO CH2OH H CH = O CH2 – OH (c) HO H (d) Both (a) and (b) H–C=O HC – OH 32. HO C – OH H H , the given is enol form of : H OH OH CH2OH (b) D-mannose (c) D-fructose (d) All of these (a) D-glucose HO- 33. D-glucose A + B; A and B are : (a) D-mannose & D-mannitol (b) D-mannose & D-Fructose (d) D-Glucose & D-Idose (c) D-Allose & D-Altrose 34. Stereoisomers of aldoheptose is (a) and stereoisomers of ketoheptose is (b). Ratio of a/b is : (b) 2 (c) 4 (d) 1 (a) 1 1 1 4 2 35. D-Glucose ¾H¾N¾O 3®( A); Product (A) is : D (a) D-Gluconic acid (b) D-Glucitol (c) D-Fructose (d) D-Glucaric acid 36. D-glucose & D-fructose can be differentiated by : (a) Fehling solution (b) Tollens reagent (c) Benedict test (d) Br2 H 2O 37. D-Glucose exist in x different forms. The value of x (stereoisomer) is : (a) 2 (b) 3 (c) 4 (d) 5 38. D-Mannose HO- D-Glucose HO- (A) ; Product (A) of above reaction is (a) D-glucose (b) D-fructose (c) D-talose (d) D-idose https://t.me/studyzee

598 39. Which of the molecules below will react with Ag + ? HO HO OH HO CH2OH O H2N (i) HO O HO OCH3 (ii) NHCH2CH2 HO OH OHOH (iii) HO OO OH HO O O HO OH OH HO OH OH (iv) OH HO O O OH HO HO CH2 HO HO O OCH3 HO HO OH OH CH2OH O (vi) O HO OCH2CH3 (v) HO OH (c) (iv) and (vi) O OH HO OH (a) (i), (iii) and (v) (b) (ii) and (iv) (d) (i), (ii), (iii) and (vi) 40. A. HO HO OH HO O HO O O OH HO OH HO O OH O HO B. HO HO HO OH HO O C. HO HO O https://t.me/studyzee

599 OH OH O HO O HO O OH OH O OH OH O O D. OH OH OH Which of the compounds (A-D) depicted above is NOT a hemiacetal linkage ? (a) Compound A (b) Compound B (c) Compound C (d) Compound D (e) None of the above (they are all hemiacetals) 41. Which of the following Fischer projection formula is same as D-Glyceraldehyde ? CH2OH CH2OH CHO CHO (b) H OH (a) OH CHO (c) OH CH2OH (d) H CH2OH CHO H HO H 42. What is the structure of the monomer from which the following polymer was made ? Ph Ph Ph Ph (a) Ph [ ]n Ph (c) Ph Ph (b) Ph (d) Ph 43. The following structure represents a subunit of a hydrocarbon polymer that may be prepared by a radical polymerization method. Identify the monomer that has been polymerized to make this polymer chain. (a) (b) (c) (d) 44. Choose the answer that has correctly identified the number of acetals and hemiacetals in isomaltose. https://t.me/studyzee