MS CHAUHAN ADVANCE

450 O 11. Compare enolate A with enolate B. O : : O O A B Which of the following statements is true ? (a) A is more stable than B (b) A and B have the same stability (c) B is more stable than A (d) No comparison of stability can be made 12. Benzalacetone is the product of mixed aldol condensation between benzaldehyde (C 6H 5CH = O) and acetone [(CH 3 )2 C = O]. What is its structure ? O || (a) C 6H 5CH = CHCCH 3 (b) C 6H 5CH = C(CH 3 )2 OO || || (c) C 6H 5CCH = CHCH 3 (d) C 6H 5CH 2CCH = CH 2 13. Identify the major product P in the following reaction: OO O || || ¾¾aq.¾Na¾O¾H ® P H + Cl O || O (a) (b) O O (c) O (d) O O || O OH 14. ¾¾PCC¾®(A) ¾d¾il. ¾NDaO¾H®(B) O O Product (B) is: (c) (d) OO (a) (b) https://t.me/studyzee

15. ( A) (i)O 3 ( B) ¾ ¾NaO¾¾H ® 451 O ¾(¾ii)Z¾n,¾H2¾O ® D C — CH 3 the reactant (A) will be : CH2 (a) (b) (c) (d) 16. Identify the principal product of the following reaction? CH2CH == O NaOH H 2O + ? CH2CH == O ¾¾¾¾¾¾¾¾® ethanol, water, heat CH == O CH == O (a) (b) CH == O OH O (d) (c) OH O 17. Which one of the following compounds is the best choice for being prepared by an efficient mixed aldol addition reaction? OH O O | || || (a) CCH2CH (b) CCHCH3 | | CH3 CH2OH O OO || || || CCH2CH2CH (c) CH2CC|HCH3 (d) HO — C — CH3 | CH3 18. Identify the major product P in the following reaction: OLi OLi OEt ¾(¾i)C¾H3¾CH¾2I T¾H¾F ® P (ii) H3O+ https://t.me/studyzee

452 O O CH3CH2O O (a) CH3 — CH2 (b) OEt OEt OO O OCH3CH2 (c) (d) OEt OEt CH2 — CH3 19. The enolate ion that reacts with 3-buten-2-one to form (Y) is : O O (Y) OO O O (a) (b) (c) (d) O O O (A), (A) + CH3 — HO–(dil) 14 O base H D H D (B) CH3 I 20. Product (B) in the above reaction is : O (a) CH3 H (b) 14 14 CH3 O 14 Br CH3 O (c) 14 O (d) CH H O || 21. H — C — D ¾¾HO¾- ®; Product of this Cannizaro reaction is : (50%) (a) D — CO - + CH 2DOD (b) H — CO - + D — CO - 2 2 2 (c) D — CO - + CH 2DOH (d) D — CO - + CHD 2OH 2 2 https://t.me/studyzee

453 22. An organic compound with the molecular formula C 9H10O forms a 2,4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizaro reaction, on vigorous oxidation it gives 1,2-benzenedicarboxylic acid. Structure of organic compound is: CHO (a) (b) CHO (d) CHO O (c) CH3 CHO OO¾® || || 23. CH 3 ¾ C ¾ CH 2 ¾ CH 2 ¾ CH 2 ¾ CH 2 ¾ C ¾ H KOH Number of intramolecular aldol condensation product is : (a) 1 (b) 2 (c) 3 (d) 4 24. ( A) ¾¾O¾3 ¾¾®(B) + (C) C7 H14 Zn AcOH Compound (A) exist in geometrical isomers and (B) gives Cannizaro reaction. (A) will be : CH 3 (b) (CH 3 )3 CCH 2 — CH == CH 2 | (a) CH 3 — CH — C == CH — CH 3 CH 3 | | CH 3 (d) CH 3 — C — CH 2 — CH == CH 2 | (c) (CH 3 )3 C — CH == CH — CH 3 CH 3 25. Which of the following compounds will not undergo Cannizaro reaction, when treated with 50% aqueous alkali? O (b) (c) Me 2CHCHO (d) Ph — CH 2 — CHO || O (a) Ph — C — H CHO https://t.me/studyzee

454 OO || || 26. H — C— D ¾¾H18¾O¾- ® D — C— 18O - + CH 2D — OH Above reaction is known as : (a) Cannizaro reaction, Disproportionation reaction (b) Tischenko reaction, Disproportionation reaction (c) Cross Cannizaro reaction, Redox reaction (d) Tischenko reaction, Redox reaction CH3 CH2 27. + CH ¾¾¾¾H¾O-¾¾¾® ( A) ; Product (A) is : (Conjugate-addition) O CO CH3 (a) (b) O O (c) (d) O CHO O OH 28. ¾(¾1)¾Ac2¾O, A¾cO¾N¾a ®( A) ; Identify product and name of reaction. (2) H2O O (a) , Aldol condensation O (b) , Perkin reaction OO O (c) , Cannizaro reaction https://t.me/studyzee

455 CH == CH — CO2H (d) , Claisen-condensation 29. Choose the most reasonable reaction intermediate for the following reaction. OO HO– (cat.) O (a) (b) O O (c) (d) None of these O OH O | || 30. CH 3 — CH — CH 2 — C— H ¾¾HO¾- ®( A) ; 3HCHO + A ¾¾Na2¾CO¾3 ® (B) (Retro aldol) 40°C (82%) Product (B) of the above reaction is : CH 2 — OH CHO | | (a) HO — CH 2 — C — CH 2OH (b) HO — CH 2 — C — CHO | | CH 2 — OH CH 2 — OH CH 2OH CHO | | (c) HO — CH 2 — C — CH 2OH (d) HO — CH 2 — C — CH 2 — CH 2 — OH | | CHO CH 2 — OH 31. CH 3CH == CHCHO ¾O¾H¾- ® ¾¾D ® A; Product A is : Aldol condensation (a) CH 3(CH == CH)3 CHO (b) CH 3CH 2CH 2(CH == CH)2 CHO (c) CH 3(CH 2CH 2 )3 CH == CH — CHO (d) none is correct https://t.me/studyzee

456 HO O H2O B. (A) and (B) are isomer : Identify (B) . 32. O (A) (b) O (a) OO (c) (d) OH 33. ¾¾H¾+ ®( A) ¾O¾Z¾n3 ®(B) ¾¾HO¾- ® (C) ; Product (C) is : D D (72%) OO (a) (b) (c) O CHO 34. C — CH3 (d) (a) O O H ¾H¾C¾l/h¾e¾at ® A. Product ( A) is: + O O || (b) Ph - C - CH 2 - CH 2 - Ph (c) Ph - CH = CH -CH -Ph (d) Ph – CH = C = CH – Ph | OH https://t.me/studyzee

457 35. Which of the following reactant on reaction with conc. NaOH followed by acidification gives the following lactone as the product ? O O O C—OCH3 CO2H (a) (b) CO2H CHO CHO CO2H (c) (d) CHO CO2H Br 36. NaOH Product; Product is: OH OH (a) (b) OH O OH (d) O (c) OH O (b) Ph—CH==C CH3 37. (P) ¾¾KO¾H ® CH3 CH3 D (d) CH3—C== CH2 (Q) ¾¾KO¾H ® Ph—CH2—OH + Ph—COs2 D (R) ¾O¾¾3 ® P + Q, Structure of (R) is : (a) Ph — CH == CH — CH 3 CH3 (c) Ph—C==CH—CH3 https://t.me/studyzee

458 38. The following reaction gives: CHO + HCHO conc.NaOH ? OMe OMe CH2OH CH2OH (a) + CH3OH (b) + HCO2 OMe OMe OMe OMe COOH COOH (c) + HCOOH (d) + CH3OH OMe OMe OMe OMe 39. Which of the following is not the product of an intramolecular aldol condensation ? OO OO (a) (b) (c) (d) Os 40. x = no. of compound better hydride donor than Ph | — Os —C | H Os Os (a) Os (b) Os O2N Os CH3O Os (c) Os (d) CH3 Os CH3 CH3 https://t.me/studyzee

459 41. Choose the reactant whose aldol reaction would give jasmone. O ? HOs heat (aldol reaction) jasmone O OO (a) (b) O O (c) (d) O O 42. Compound X undergoes the following reaction sequence. What is the structure of compound X? OH X ¾¾NaO¾¾H ® ¾¾He¾at ® ¾¾H2 ¾P¾d ® ¾1¾. Li¾AlH¾4 ® 2. H2O HO (b) HO (a) (d) O O (c) 43. Predict the major product of the following reaction sequence OLi O 1. 2. H2O O H CH3 + NaOH H3C –H2O Heat CH3 O O OO (a) (b) CH3 https://t.me/studyzee

460 CH3 O O OO (c) (d) CH3 44. CHO ¾C¾on¾cD. K¾O¾H ® ( A) ¾¾HD¾r ® (B) CHO Cyclic product Structure of (B) is : COOH (c) O COOK O CH2OH O CH2OH (a) O (b) (d) 45. Which of the following is not the product of an intramolecular aldol condensation ? OO OO (a) (b) (c) (d) 46. (X) Conc. KOH (Y) HÅ O D O Compound (X) is obtained by which of the following reaction ? O (a) CH2—OH 2 moles of PCC (b) C—O—Et 2 moles of DIBAL-H CH2—OH in CH2Cl2 C—CH3 O https://t.me/studyzee

461 OO (c) C—Cl 2H2 (d) CH3MgBr H CH2—C—Cl Pd – BaSO4 H 47. O == C—C == O OH O == C—C—OH H OH Given reaction is Cannizaro reaction at normal concentration of base. Predict the order of above reaction (a) 1 (b) 2 (c) 3 (d) 4 OH + HCOs2KÅ 48. (A) (1) O3/Zn (2) conc. KOH HBr (B) (c) (d) CCl4 major Product (B) is : (a) (b) Br Br 1. (a) 2. (b) ANSWERS — LEVEL 1 6. (c) 7. (b) 8. (b) 9. (b) 10. (c) 14. (b) 15. (a) 16. (b) 17. (b) 18. (a) 3. (a) 4. (b) 5. (b) 22. (b) 23. (c) 24. (c) 25. (d) 26. (a) 11. (a) 12. (a) 13. (a) 30. (c) 31. (a) 32. (a) 33. (c) 34. (a) 19. (c) 20. (a) 21. (c) 38. (b) 39. (c) 40. (b,c) 41. (d) 42. (d) 27. (c) 28. (b) 29. (c) 46. (a) 47. (b) 48. (b) 35. (c) 36. (b) 37. (b) 43. (c) 44. (a) 45. (c) https://t.me/studyzee

462 Level - 2 1. Comprehension Mechanism of Cannizzaros reaction of benzaldehyde is O O- O O Ph C HO– Ph C H + C Ph ¾slo¾w® Ph C OH + Ph CH2 O– | CO-2 + Ph CH2 OH H OH H Ph A. Which of the following reactants can undergo Cannizaro's reaction.? O (a) H C H (b) R 3CCHO (c) (d) All of these O CHO B. Order of the above reaction is: (a) 1 (b) 2 (c) 3 (d) 4 C. Which of the following is best hydride donor in Cannizaro's reaction? CHO CHO (a) (b) OMe NO2 CHO CHO (c) (d) CH3 Cl D. Cannizaro's reaction is: (a) Reduction (b) Disproportionation reaction (c) Oxidation (d) Ion - exchange reaction E. Which of the following cannot undergo intramolecular Cannizaro's reaction? https://t.me/studyzee

463 OO OO (a) H C C H (b) H C C Ph OO OO (c) Ph C C Ph (d) H C C H 2. Aldol condensation proceeds by carbon-carbon bond formation between an enolate donor and a carbonyl acceptor. For each of the following aldol products (a through e) select a donor and an acceptor compound from the list at the bottom of the page (compounds A through H). Write the letter corresponding to your selection in the appropriate answer box. Aldol Product Donor Acceptor OH a. CHO O b. OH O c. CH d. (CH 3)2C(OH)CH 2COCH 3 e. CO2C2H5 (A) (E) CO2C2H5 CHO (B) O (C) CHO (D)H 2C == O OO CO2C2H5 (G) (F) H2C H3C (H) CHO CH3 CO2C2H5 https://t.me/studyzee

464 3. Comprehension During an experimental workup procedure, a chemist treated a starting material with NaOH in the solvent acetone [(CH 3)2C == O]; however, the starting material was recovered unreacted. Instead, the chemist isolated a small amount of Product A (shown below). Product A The chemist determined that Product A resulted from the aldol self-condensation of acetone. Product A was identified based on the following observations. Observations about Product A 1. Elemental analysis of Product A indicated that it consisted only of carbon, hydrogen, and oxygen. 2. product A had a molecular weight of 116 g/mol. 3. Product A was a methyl ketone because it gave a positive iodoform test. 4. When product A was treated with Br2 in CCl 4 , the red bromine colour persisted, because no carbon-carbon double bonds were present to react with the bromine. The structure of Product A was further confirmed when treatment with hot sulfuric acid resulted in the corresponding dehydration product, Product B. A. What is the molecular weight of a compound that undergoes an aldol self-condensation reaction to result in a b-hydroxy ketone with a molecular weight of 144 ? (a) 70 g/mol (b) 72 g/mol (c) 74 g/mol (d) 76 g/mol B. The aldol self-condensation of acetone is an equilibrium that favours acetone over its condensation product. Which of the following experimental modifications is most likely to shift the position of equilibrium toward Product A ? (a) Using only a catalytic amount of NaOH (b) Using only a catalytic amount of acetone (c) Removing Product A as it is formed (d) Increasing the reaction temperature to the boiling point of acetone C. Based only on observation 1 and 2, which of the following compounds could have been Product A ? O OH || | (a) CH 3CH CH 2CH 2CH 2CH 2CH 3 (b) CH 3C CH 2 CH CH 2CH 2CH 3 | CH3 OH (c) CH 2 == CHCH 2 - O - CH 2CH 2CH 3 (d) OH https://t.me/studyzee

465 D. When a drop of Br2 in CCl 4 is added to Product B, the resulting solution will be : (a) colourless, because Product B does not contain a carbon-carbon double bond (b) colourless, because Product B contains a carbon-carbon double bond (c) red, because Product B does not contain a carbon-carbon double bond (d) red, because Product B contains a carbon-carbon double bond E. Which of the following compounds from the passage will give a positive iodoform test ? (a) Product A only (b) Product A and Product B (c) Product A and acetone only (d) Product A, Product B, and acetone 4. Comprehension conc. KOH Benzyl alcohol + salt of benzoic acid A O3 B + C O dil. KOH CH3—CH—CH2—C—H OH HCN D H3O r E D A. Structure of A is : (b) Ph — CH == CH — CH 3 (d) Ph — CH == C — CH 3 (a) H 2C == CH — CHO (c) Ph — C == CH 2 | CH3 | CH3 B. Structure of (B) and (C) differentiated by : (a) Tollen’s reagent (b) Fehling solution (c) 2,4-DNP (d) NaHSO 3 C. Structure of E is : OH (a) (b) HO O OO OH OO Me OH (c) O (d) O 5. Comprehension An organic compound ‘P’ with molecular formula C 8 H 8 O forms an organic red ppt with 2, 4-DNP gives yellow ppt. on heating with I2 in presence of NaOH. It neither reduces Tollen’s or Fehling reagent nor does it decolourise Br 2 water or Baeyer’s reagent. On drastic oxidation with chromic acid (H 2CrO 4 ) it gives an acid (Q) having molecular formula C7 H 6O 2. https://t.me/studyzee

466 A. Identify compound P : OH O O O C—CH3 (c) C—H CH3 (d) H2C (a) (b) CH3 H3C (d) NaOH/CaO / D (d) 6 B. Q ¾¾¾¾¾¾® R (Major product) R will be : Ph (a) (b) (c) s CH3MgBr (1mole) dil. OH C. P ¾¾¾® S ¾¾¾¾¾¾® D H3O Å No. of stereoisomer in the final product T : (a) 2 (b) 3 (c) 4 Subjective Problems O O OH O OO 1. H H OH H HH OH OH OH (A) (B) (C) (D) (E) O O OH O OH OO HO HO HO (F) (G) (H) (I) (J) X = Number of compound obtained by aldol reaction Y = Number of compounds react with NaHCO 3 Sum of X + Y is 2. In the scheme given below, the total number of intramolecular aldol condensation products formed from ‘ Y ’ is : ¾¾1¾.O 3¾¾® Y ¾1¾. N2¾a.OheH¾a(ta¾q)® 2. Zn,H2O https://t.me/studyzee

467 O HO O OH || 3. CH 3 — C — CH 3 + x HCHO ¾¾KO¾H ® HO C OH HO HO x = moles of HCHO consumed. Value of ( x) will be OO || || 4. CH 3 — C — CH 3 + CH 3 — CH 2 — C — CH 3 ¾¾KO¾HD(¾aq¾.) ® ( X) X = number of aldol condensation product (including stereoisomer). Find out the value of ( X ) . ANSWERS — LEVEL 2 1. A – d; B – c; C – a; D – b; E - c 2. a – Donor = C, Acceptor = C; b – Donor = E, Acceptor = D; c – Donor = B, Acceptor = A; d – Donor = G, Acceptor = G; e – Donor = F, Acceptor = B 3. A – b; B – c; C – d; D – b; E - d 4. A – b, B – b, C – c 5. A – c, B – a, C – c Subjective Problems 1. 6 2. 3 3. 6 4. 9 https://t.me/studyzee

468 9 CARBOXYLIC ACID AND THEIR DERIVATIVES Level - 1 1. Identify C in the following sequence of reactions : CO2H ¾S¾OC¾¾l2 ® ¾¾NH¾3 ® ¾ ¾P4O¾10 ® A B heat C(C 8H13N) CH3 OH CN CN CN CH3 (a) (b) (c) (d) CH3 CH3 CH3 2. Saponification (basic hydrolysis) of C 6H 5 C O CH 3 will yield : || O [ O = mass – 18 isotope of oxygen] OO || || (a) C 6H 5 — C — O- +HO CH 3 (b) C 6H 5 — C — O - +H OCH 3 (c) C 6H 5 C O - + HO- (d) C6H 5 CO - + HOCH 3 || || O O O C – Cl 3. ¾¾Me2¾N¾H ® ( X ) 0°C, 2h 86-89% (yield); (3 equivalent) https://t.me/studyzee

469 Product (X) of the reaction is : OH O Me C – NMe2 N (b) NMe2 (a) Me O (c) C–H (d) 4. Which of the following is the correct order of decarboxylation of b-keto carboxylate anion ? O O O– R OO O– OO OO R–C F Cl R O– R O– (a) NO2 CN (b) (c) (d) (a) a > b > c > d (b) c > d > a > b (c) c > d > b > a (d) d > c > a > b OO ClC CCl 5. + CH 3 - NH 2 ¾¾® Product of the reaction is : (A) C|H3 N N (a) O (b) HO CH3 O OO NH (d) (c) | ||O NH O 6. Which b-keto acid shown will not undergo decarboxylation ? CO2H OO (a) (b) CO2H O O || || (d) CH 3 - C - CH 2 - CO 2H (c) Ph - C - CH 2 - CO 2H https://t.me/studyzee

470 7. Choose the response that matches the correct functional group classification with the following group of structural formulas. H H OO ONO NO (a) Anhydride Lactam Lactone (b) Lactam Imide Lactone (c) Imide Lactone Anhydride (d) Imide Lactam Lactone OH 8. CO2H ¾(¾1) ¾Et-¾Li(¾3-¾eq¾.)® (P) ; Product (P) of the reaction is : (2) H+, H2O (65% yield) OH OH OEt OEt OH Et Et OH Et (a) Et (b) O (c) Et Et (d) Et O OH 9. OH conc. H2SO4 (X) + H 2O OH 89-91% yield (Lactic acid) Product (X) of the reaction is : O (a) OH (b) O O O OH OO (c) O (d) OH OH MeO OMe ¾H¾3O¾¾Å ® (A) , Product (A) obtained is : 10. EtO2C CO2Et D O O O O CO2Et O CO2H (a) (b) (c) (d) https://t.me/studyzee

471 11. Which of the following acid on heating gives geometrical isomers as a product ? OH CO2H (b) CO2H | (a) CH 3 - CH - CO 2H Cl (c) CH 3 - CH - CH 2 - CO 2H (d) All of these | OH O 12. O ¾¾MeO¾¾H ® A ¾¾PC¾l3 ® B ¾¾MeN¾H¾2 ® C ; Product (C) of the reaction is : (a) (c) || O O || C – NH – Me O (b) C – Cl C – O – Me || C – NH – Me O O O O || NH2 C – Cl OMe (d) O O C – NH2 || O 13. O ¾¾LiAl¾H¾4 ® A ¾P¾C¾C ® B ¾N¾H¾2-N¾H¾2 ® C , Product (C) is : || O O OH NH2 NH | NH2 NN (a) (b) N (c) N (d) NH | OH O Cl O | O– ¾-¾CO¾2 ® A ¾H¾¾Cl ® B ¾a¾q K¾O¾H ® C. Product (C) is : 14. Cl O OH || | (a) CH 3 — CH 2 — C — H (b) OH O O (c) (d) CH3 H CH3 https://t.me/studyzee

472 Cl 15. O +R - CH 2 - NH 2 ¾K¾2C¾O¾3 ® ( A) THF (71%) O In above reaction identify major product (A) of the reaction: (a) (b) OH N – CH2 – R N – CH2 – R O O (c) NH – R (d) OH O N–R OO 16. An optically active compound ‘X’ has molecular formula C 4H 8O 3. It evolves CO 2 with NaHCO 3. ‘X’ reacts with LiAlH 4 to give an achiral compound. ‘X’ is : (a) CH 3CH 2CHCOOH (b) CH 3CHCOOH | | OH Me (c) CH 3C|HCOOH (d) CH 3CHCH 2COOH | CH2OH OH O || 17. CH 3 - C - O - CH 2 - CH 3 + H – O – ¾¾® (O = O18) One of the product of the reaction is : O || (a) CH 3 - C - O - H (b) CH 3 - CH 2 - O -H O (d) CH 3 - CH 2 - O – || (c) CH 3 - C - O – O COCH2CH3 18. CH3CH2OC COCH2CH3 ¾¾KO¾H ® ¾¾H3O¾¾+ ® ¾¾PC¾l5 ® ¾L¾iAl¾H¾4 ® ¾H¾+¾/¾D ®( X ) O O Product (X) is : https://t.me/studyzee

473 (a) (b) (c) (d) 19. Identify final product in the following reaction; CH 3CHCOOH ¾¾D ® Product | OH O O O CH3 || (a) (b) CH 2 == CHCO 2H (c) CH 3 — C CO 2H (d) CH 3CH 2OH H3C O O 20. Select the final product from this sequence of reactions. Acetoacetic ester ¾¾NaO¾¾Et ® ¾C¾H¾3I ® ¾N¾aO¾¾Et ® ¾C¾H3¾CH¾2CH¾2B¾r ® O CH3 CH3 || | | (a) H 3C - C -C - COOC 2H 5 (b) H 3C -C - CH 2COOC 2H 5 | | CH2CH2CH3 CH2CH2CH3 H CH3 | | (c) H 3C - C - CH 2COOC 2H 5 (d) CH 3CO – C – CH 2COOC 2H 5 | | CH2CH2CH3 CH3 Et CO2CH2 – CH3 21. O ¾H¾2O¾, H¾2SO¾¾4 ® (A) ; Product (A) will be : heat CO2Et O O O O (c) (d) CO2H (a) (b) (i) Na 22. CH 2(CO 2Me) 2 + ? ¾(¾ii) ¾AcO¾¾H ® CH(CO 2Me) 3 Which of the following reactants will complete the above reaction ? (a) CH 2(CO 2Me)2 (b) (CO 2Me)2 (c) Cl - CO 2Me (d) COCl 2 23. Arrange the following in order of increasing reactivity (least ¾® most) towards nucleophile O O O || || || CH 3C OCHCH 3 CH 3C Cl CH 3C NHCH 3 1 2 3 (a) 1 < 2 < 3 (b) 3 < 1 < 2 (c) 1 < 3 < 2 (d) 2 < 1 < 3 https://t.me/studyzee

474 24. Choose the best sequence of reactions for transformation given. Semicolons indicate separate reaction steps to be used in the order shown. O || H3C CO2CH3 ¾¾? ® H3C C NH CH3 (a) H 3O + ; SOCl 2 ; CH 3NH 2 (b) HO - H 2O ; PBr3 ; Mg; CO 2 ; H 3O - ; SOCl 2 ; CH 3NH 2 (c) LiAlH 4 ; H 2O; HBr; Mg; CO 2 ; H 3O + ; SOCl 2 ; CH 3NH 2 (d) None of these would yield the desired product 25. A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of : + OH O || || (b) H 2O to CH 3 C NH 2 (a) H 3O + to CH 3C NH 2 + OH + OH || || (c) H 3O + to CH 3 C NH 2 (d) HO - to CH 3 C NH 2 26. Which reaction is not possible for acetic anhydride ? OO || || + - (a) (CH 3C )2 O + 2HN(CH 3 )2 ¾® CH 3C N(CH 3 )2 + CH 3CO 2 + H2 N(C H 3 )2 OO || || (b) (CH 3C )2 O + CH 3CH 2OH ¾® CH 3C OCH 2CH 3 + CH 3CO 2H OO || || (c) + C6H 6 ¾ ¾AlC¾l3 ® CH 3 C 6H 5 + CH 3CO 2H (CH 3C )2 O C OO || || (d) (CH 3C )2 O + NaCl ¾® CH 3C Cl + CH 3CO -2Na + 27. All but one of the following compounds react with aniline to give acetanilide. Which one does not? O NH2 NHCCH3 Aniline Acetanilide OO (b) H3C || || O (d) O CH3 || O (a) CH 3 C —Cl || OCCH3 O || (c) CH 3C —H 28. Which of the following best describes the nucleophilic addition step in the acid-catalyzed hydrolysis of acetonitrile (CH 3CN) ? https://t.me/studyzee

475 (a) H3C – C º N + O– (b) H3C – C º N – H H O– H (c) H3C – C º N + (d) H3C – C º N – H OO HH HH 29. The major product expected, when Phthalamide is treated with NaOH, is : (a) OH OH ONa (b) OH O O O || (c) ONa O ONa (d) O O || O 30. Which of following acid remains unaffected on heating ? (a) malonic acid (b) maleic acid (c) Fumaric acid (d) Succinic acid 31. Br ( )n Br + CH 2(CO 2Et)2 ¾N¾EatOO¾¾HEt ® cyclic product At which value of n the formation of six membered ring takes place ? (a) n = 2 (b) n = 3 (c) n = 5 (d) n = 6 O 32. N ¾L¾iAl¾H4¾(ex¾ces¾s)® Product of the reaction is : O CH2OH H 2O (a) CH2OH NH2 (b) OH (c) N (d) N 33. CO2H OH CO2H ¾(¾-CD¾O¾2)® ¾(¾-HD¾2O¾)® , Product of the reaction is : CO2H https://t.me/studyzee

476 (a) cis-anhydride (b) trans--anhydride (c) both (a) & (b) (d) mono-basic acid CO2H CO2Et (b) (i) EtOH, HCl 34. ¾¾¾¾¾® ( A) O (ii) EtMgBr O || (iii) H+ D C – CH3 O Product (A) of the reaction is : (d) CH3 OH CH3 CO2Et (a) HO Et O (c) C – CH3 O CH 2 – O – COR | 35. CH – O – COR 2 + 3NaOH ¾® (A) + Salt of fatty acid (soap) | CH 2 – O – COR 3 Product (A) of the reaction is : (a) Ethylene glycol (b) Glycerol (c) Glyceryltrinitrate (explosive) (d) Cumene hydrogen peroxide 36. CH 3 - CH - OAc ¾¾HO¾– ® Product of the reaction is : | Et (d=dextro rotatory) (d) Et | (a) CH 3 -CH - OH (b) CH 3 - CH - OH (c) CH 3 - CH - OH (d) CH 3 -C = CH 2 (d) | | | Et Et CH3 (l) (d) & (l) O || (i) SOCl2 (A) ; Product (A) of the reaction is : 37. Ph - CH = CH -C -O - H (ii) NH2 O O || || (a) Ph - CH = CH -C -CH 2 - NH (b) Ph - CH = CH -C -NH O (d) Ph – CH = CH – NH || (c) Ph - CH = CH - C – H https://t.me/studyzee

477 OO || 38. Ph - C - Cl + ¾¾® ( A) ; Identify the product (A). N (Major) | H (Morpholine) OO (a) Ph – C – O N–H (b) Ph – C – N O O O O (c) Ph – C – N || (d) Ph - C - NH 2 OMe OH Conc. HCl O O 39. + + MeOH O Above reaction is an example of : (a) Esterification (b) Saponification (c) Hydrolysis (d) Trans Esterification 40. Which of the following is an intermediate formed in the reaction shown below ? O || CH 3 - C - Cl + NH 3 ¾¾® Intermediate ¾¾® product. O || Å (b) CH 3 - C Å (a) CH 3 - N H 3 O– OH || (c) Cl - C - Cl (d) CH 3 - C - Cl | | Å NH3 Å NH3 O OR 41. R O O R ¾¾NaO¾H,¾H2¾O ® Product OO 100°C (several hours) (Principal component of coconut oil.) Product is obtained in the above reaction is : OH (a) R - CO 2Na (b) (c) Both (a) and (b) (d) None of these OH OH 42. The reaction of sodium acetate with acetyl chloride proceeds through which of the following mechanisms ? O O O O + CH3 – C – Cl – + CH3 – C – Cl || – (b) CH3 – C – O (a) CH3 – C – O https://t.me/studyzee

478 O O O O – + CH3 – C – Cl – + Cl – C – CH 3 (c) CH3 – C – O (d) CH3 – C – O 43. Which is the major product of the following reaction ? O || CH 3 - ¾¾H¾2S ® product C - Cl OH O S OO | || || || || (a) CH 3 -C - Cl (b) CH 3 - C - SH (c) CH 3 - C- Cl (d) CH 3 - C - S - C - CH 3 | SH 44. Which is the major product of the following reaction ? O O + CH 3 - NH 2 ¾D® product O N – CH 3 O (a) N – CH3 (b) O OO OO || || (c) HO - C - CH 2 - CH 2 - C - NH - CH 3 OO || || (d) CH 3 - NH - C - CH 2 - CH 2 - C - NH - CH 3 45. Ethanoic acid + 3-methyl-1-butanol traces ( A); Compound (A) is : O H2SO4 (a) O O (b) || O O O (c) (d) O O O || C 46. O ¾¾PC¾l5 ®( A) ¾¾LiAl¾H¾4 ®(B) ¾¾PC¾C ®(C) ¾¾HO¾– ®(D) D C O https://t.me/studyzee

479 CH2 – OH – CH2 – OH CH2 – O– CO2 (a) – (b) – (c) (d) – CO2 CO2 CH2 – OH CH2 – O 47. Which of the following compounds will undergo decarboxylation on heating ? OO CO2H CO2H CO2CH3 O CO2H O 2 34 1 (a) 2 and 3 (b) 3 and 4 (c) 3 only (d) 1 and 4 48. Which one of the following is not an intermediate in the generally accepted mechanism for the reaction shown below ? OO || || + CH 3 CH CH 3 ¾ H¾2S¾O¾4 ® CF3 O CH CH 3 + H 2O CF3 C OH C | | OH CH3 +OH O– || | (b) CF3C| – OCH(CH3)2 (a) CF3C – OH OH OH OH | | (c) CF+3CO| H–2 OCH(CH3)2 (d) CF3C| – OCH(CH3)2 OH 49. RO 3 eq. EtOH ¾d¾ry¾HC¾l ga¾s ¾¾® (A); Product A is : CO2H (major product); (a) RO CO2R (b) RO CO2Et (c) EtO CO2Et O || (d) R - O - C - O - Et 50. Identify the compound C in the following sequence : (CH 3)2 CHCH 2C º N ¾H¾Cl¾, H¾2¾O ® compound A ¾1¾. L¾iAlH¾¾4 ® compound B 2. H2O ¾C¾HPC2¾CC¾l2 ® compound C https://t.me/studyzee

480 O O || || (a) (CH 3 )2 CHC CH 3 (b) (CH 3 )2 CHCH 2 C OH OO || || (c) (CH 3 )2 CHCH 2 C H (d) (CH 3 )2 CHC CH 2OH 51. What is the final product (B) of this sequence ? CH3 ¾¾Br¾2 ® A ¾ 1. KCN B ¾2. H¾3O¾+, ¾¾® light heat CH3 CO2H CH3 CH2CO2H CO2H (b) (c) (d) (a) CO2H 52. Which of the following undergoes decarboxylation most readily on being heated ? O (b) (a) OH O O HO O (c) HO OO (d) OH O 53. What is compound Z ? HO O CH 3CH 2CH 2Br ¾N¾aC¾¾N ® X ¾H¾3O¾+ ® Y ¾C¾H3¾CH¾2O¾H ® Z heat H+ O || (a) CH 3CH = CHC OH (b) CH 3CH 2CH 2CH = NOCH 2CH 3 (c) CH 3CH 2CH 2CH(OCH 2CH 3 )2 O || (d) CH 3CH 2CH 2 C OCH 2CH 3 CN H¾3¾O Å®/ D 54. CN (A); Product (A) of the reaction is : CN CN OO (a) O (b) O O O https://t.me/studyzee

481 CO2H O (c) (d) O CO2H O 55. CH 3 - CH = CH - CH 2 - CO 2H ¾¾® (X) (major); Product (X) is : D (a) CH 3 - CH = CH - CH 3 (b) CH 3 -C = CH 2 (c) CH 3 - CH 2 - CH = CH 2 | CH3 (d) CH 3 - CH = CH 2 OO || || 56. H -O - C -(CH 2 )n - C-O -H ¾¾® product , At what value of (n) given compound will D not evolve CO 2 gas ? (b) n = 4 (c) n = 2 (d) n = 1 (a) n = 5 CO 2H (d) Oxalic acid | 57. (CH 2 )n ; If (n = 4) then di-carboxylic acid would be known as : | CO 2H (a) Malonic acid (b) Succinic acid (c) Adipic acid 58. ¾¾2H2¾O ®( A) O OC O O Product (A) of the above reaction is : HO CH3 CO2H (b) O CO2H CO2H OH CO2H (a) O OH C—H (c) HO CO2H (d) HO H HO CO2H O HO https://t.me/studyzee

482 2H 2 OO Pt CO2H + HO — C — C — O — H CO2H 59. (AW) armKcMonncO.4 cis-cyclo hexane Identify (A). 1,2-dicarboxylic acid (a) (b) (c) (d) CO2H CO2H 60. CH3 CH3 How many product will be formed when above compound undergo de-carboxylation? (a) 0 (b) 1 (c) 2 (d) 3 HH CH3 H H CH3 ¾(¾-CD¾O¾2)® Product of the reaction is : 61. CO2H HH CO2H H HH H (a) CH3 H H CH3 (b) CH3 CH3 H H H CO2H HH H H CO2H H (c) Both (a) and (b) (d) none of these 62. Products obtained in the given reactions are shown below. CO2H CO2H CO2H D CO2 + x , CO2HBr D CO2 + y Br Br Br (cis) (trans) https://t.me/studyzee

483 The number of possible products for x and y are : (a) 1, 1 (b) 1, 2 O (c) 2, 1 (d) 2, 2 CH2 – Br (1) –Å N K + DMF O 63. ( A) (2) HO– /H2O ( 81%) (Benzyl bromide) Product ( A) of the above reaction is : (b) Ph - CH 2 - NH 2 (d) Ph - CH 2 - NH - CHO (a) Ph - NH 2 (c) Ph - CH 2 - NH - CO 2H (b) D-Glucose, D-Mannose 64. Which of the following pair is C 2-epimer ? (d) D-Glucose, D-Arabinose (a) D-Glucose, D-Maltose (c) D-Allose, D-Ribose 65. Total number of enol possible for the compound formed during given reaction will be (including stereoisomer): O || CH 3MgBr + CH 3CH 2 — C — Cl ¾® (a) 2 (b) 3 (c) 4 (d) 5 66. What is the product of the following reaction ? O O O O ¾ ¾H3O¾+,¾H2¾O ® O O (a) HO OH (b) HO O O OH O O O (d) O O O (c) HO OH HO O OH 67. CH3 ¾(¾i) K¾BrO¾,¾D ® ( X ) ¾¾D ® (Y ) COOH (i)H+ Hence the product (Y ) in the above sequence of reactions, is : O O O OH COOH CH3 (a) CH3 (b) (c) (d) https://t.me/studyzee

484 O O 68. C—NH2 15 and C—NH2 s ¾¾OH¾/B¾r2¾® Products are : (Intramolecular migration) CH3 C2H5 (a) NH2 15 NH2 15 and and NH2 NH2 (b) CH3 Et CH3 15 Et NH2 NH2 15 NH2 (d) and NH2 (c) and CH3 Et CH3 Et 69. CH 3CH 2CH(OH)CH(CH 3 )2 + CH 3COCl ¾b¾ase® CH 3CH 2CH(OCOCH 3 )CH(CH 3 )2 + HCl In the above reaction, if the reactant alcohol is a pure R-isomer the product would. (a) have configuration inverted at the chiral atom (b) be a racemic mixture (c) have the same configuration at the chiral atom (d) be optically inactive 70. The order of SN 1 reactivity in aqueous acetic acid solution for the compounds O H3C—C—CH2—Cl H3C—CH2—CH2—Cl (H3C)3C—Cl (1) (2) (3) (d) 3 > 1 > 2 (a) 1 > 2 > 3 (b) 1 > 3 > 2 (c) 3 > 2 > 1 ANSWERS — LEVEL 1 1. (b) 2. (b) 3. (a) 4. (c) 5. (a) 6. (b) 7. (d) 8. (b) 9. (b) 10. (b) 11. (d) 12. (b) 13. (b) 14. (a) 15. (b) 16. (c) 17. (c) 18. (b) 19. (a) 20. (a) 21. (b) 22. (c) 23. (b) 24. (a) 25. (b) 26. (d) 27. (c) 28. (d) 29. (c) 30. (c) 31. (b) 32. (c) 33. (a) 34. (a) 35. (b) 36. (a) 37. (b) 38. (b) 39. (d) 40. (d) 41. (c) 42. (c) 43. (b) 44. (c) 45. (b) 46. (a) 47. (c) 48. (b) 49. (b) 50. (c) 51. (d) 52. (d) 53. (d) 54. (d) 55. (c) 56. (c) 57. (c) 58. (c) 59. (b) 60. (b) 61. (c) 62. (c) 63. (b) 64. (b) 65. (b) 66. (c) 67. (c) 68. (b) 69. (c) 70. (c) https://t.me/studyzee

485 Level - 2 1. Match the Column (I) and (II). (Matrix) Column (I) Column (II) Products formed Reaction Diastereomers CH3 Racemic mixture HO2C CO2H ¾¾® (p) (a) H DD Ph CH3 (b) HO2C CO2H ¾¾® (q) D Et CO2H CO2H (c) ¾¾® (r) Meso compound D CH3 (d) CO2H ¾¾® (s) CO 2 gas will evolve CO2H D https://t.me/studyzee

486 Subjective Problems O HO2C CO2H 1. HO2C CO2H ¾¾D ® ( X) mole of CO 2 ­ ; HO2C CO2H O (Y ) ¾¾D ® Ph b-Keto acid (Y ) is including stereoisomers. Value of ( X + Y ) will be ANSWERS — LEVEL 2 1. a – p, s; b – q, s; c – p, s; d – r Subjective Problems 1. 8 https://t.me/studyzee

487 10 AMINES Level - 1 1. In which of the following reaction cyanide will be obtained as a major product ? O O || || (a) Ph - C - CH 3 ¾(¾(ii)i)L¾HiA3lO¾H¾+4 ® ¾N¾aO¾¾H ® (b) Ph - C- NH 2 Br2 O O || || (c) Ph - C - NH 2 ¾P¾4O¾10 ® (d) Ph - C - O - H ¾S¾OC¾l2 ® ¾N¾H¾3 ® NH2 2. ¾H¾NO¾¾2 ® A (Major) : Product ( A) is : NH–NO2 O–NO OH (a) (b) (c) (d) https://t.me/studyzee

488 3. Which of the following alkene cannot be prepared by de-amination of n-Bu – NH 2 with NaNO 2 HCl ? (n- Butyl) (a) 1-butene (b) cis-2-butene (c) trans-2-butene (d) Iso-butene 4. Predict the major product P in the following reaction. OH Me Me Me ¾H¾NO¾¾2 ® P NH2 O Me OH Me Me (a) (b) Me Me OH Me Me Me OH Me (c) Me (d) CH2 OH Me 5. ¾N¾aN¾O¾2 ® (A); Product of this reaction is : H 2SO 4 NH2 (a) (b) (c) (d) OH 6. CH2 – NH2 ¾H¾NO¾¾2 ® ( A) + + CH2 = CH – CH2 – CH2 – OH 48% 47% CH2OH A will be : (a) CH 2 = CH -CH - CH 3 (b) | OH (c) (d) 7. Which of the following isomers of C 8H 9NO is the weakest base ? (a) o-Aminoacetophenone (b) p-Aminoacetophenone (c) m-Aminoacetophenone (d) Acetanilide https://t.me/studyzee

489 8. Rank the following compounds in order of increasing basic strength. (weakest ® strongest) : NH2 CH2NH2 NH2 O NO2 || CNH2 12 3 4 (a) 4 < 2 < 1 < 3 (b) 4 < 3 < 1 < 2 (c) 4 < 1 < 3 < 2 (d) 2 < 1 < 3 < 4 9. Which of the following arylamines will not form a diazonium salt on reaction with sodium nitrite in hydrochloric acid ? (a) m-Ethylaniline (b) p-Aminoacetophenone (c) 4-Chloro-2-nitroaniline (d) N-Ethyl-2-methylaniline 10. Identify product D in the following reaction sequence : CH 3 | CH 3 – C – CH 2CH 2OH ¾ K¾2C¾r2O¾7 ; H¾2S¾O¾4 ® A ¾S¾OC¾l2 ® B ¾(¾CH¾3 )2¾N¾H ® C 1. LiAlH4 | H2O, heat (2 mole) ¾d¾iet¾hyl¾eth¾¾er ® D 2. H2O CH 3 CH 3 CH 3 | | (b) CH 3CCH 2CH 2N(CH 3 )2 (a) CH 3CCH 2C º N | | CH 3 CH 3 CH 3 N(CH 3 )2 CH 3 || | (c) CH 3CCH 2CHN(CH 3 )2 (d) CH 3CCH 2 CHN(CH 3 )2 | || CH 3 CH 3 OH 11. Which one of the following is best catalyst for the reaction shown below ? CH 3(CH 2 ) 8 CH 2Br ¾K¾C¾N ® CH 3(CH 2 ) 8 CH 2CN benzene (a) CH3Cl (b) NH2 (c) CH2+N(CH3)3Cl– O || (d) NHCCH3 12. The major products obtained from the following sequence of reactions are : (CH 3 )2 CHCH 2N(CH 2CH 3 )2 ¾C¾H¾3 I ® ¾A¾g 2¾O ® ¾h¾e¾at ® products H 2O (a) (CH 3 )2 CHCH 2NH 2 + H 2C = CH 2 (b) (CH 3 )2 NCH 2CH 3 + H 2C = C(CH 3 )2 CH3 |+ (c) (CH 3 )2CHCH 2N CH 2CH 3 + H 2C = CH 2 (d)(CH 3 )3 N CH 2CH 3I- + H 2C = CH 2 https://t.me/studyzee

490 13. Which amine yields N-nitroso amine after treatment with nitrous acid (NaNO 2 ,HCl) ? (a) CH2NH2 (b) H3C NH2 (c) N (d) NHCH3 H 14. OH ¾H¾NO¾¾2 ® ( A); Product ( A) is : NH2 H (a) cyclopentane carboxyaldehyde (b) cyclohexane-1, 2-diol (c) 2-aminocyclohexene (d) cyclohex-2-enol 15. Choose the appropriate product for this reaction. CN ¾1¾. L¾iA2l.H¾H43(O¾ex+c¾es¾s)® product (a) (b) CH2NH2 NH2 (c) OH (d) NH2 16. Which of the following product will be obtained in the given (consider minor product also) Beckmann-type rearrangement ? O O Me ¾(¾1)N¾H2¾OH¾,H¾Cl ® product O (2)PCl5, D O H Me O O (a) N (b) Me O O O N O H (c) O (d) all of these N Me 17. Deamination (or) diazotization of n-Bu–NH 2 with NaNO 2 HCl gives ......... isomeric butene. (a) 2 (b) 3 (c) 4 (d) 5 https://t.me/studyzee

491 OH OO || || 18. ¾A¾c2¾O ® P ¾A¾c2¾O ® Q Ac 2O == CH 3 — C — O — C — CH 3 NH2 P and Q respectively are : O OH O O || || || O—C—CH3 C—O—CH3 C—O—CH3 (a) , , (b) NH2 NH—C||—CH3 NH2 NH—C||—CH3 OH OH OO OO , || || C—O—CH3 O—C—CH3 (c) (d) , NH—C||—CH3 NH—C||—CH3 NH—C||—CH3 NH—C||—CH3 O O O O 19. A nitrile X is treated with LiAIH 4 to obtain compound Y (C 2H7N). In a separate reaction X is hydrolyzed in an acid medium to obtain Z. The product obtained after mixing Y and Z will be (a) CH 3CONHCH 2CH 3 (b) CH 3CH 2CONHCH 2CH 3 (CH 3COO – + – + (c) )(CH 3CH 2NH 3 ) (d) (CH 3CH 2COO )(CH 3NH 2 ) 20. The compound X(C7H 9N) reacts with benzensulfonyl chloride to give Y(C13H13NO 2S) which is insoluble in alkali. The compound X is: NHCH3 NH2 (a) (b) CH3 NH2 NH2 (c) (d) CH3 H3C 1. (c) 2. (a) 3. (d) ANSWERS — LEVEL 1 6. (b) 7. (d) 8. (b) 9. (d) 10. (b) 11. (c) 14. (a) 15. (b) 16. (d) 17. (b) 18. (d) 19 (c) 4. (a) 5. (b) 12. (c) 13. (d) 20. (a) https://t.me/studyzee

492 Level - 2 1. Five amine syntheses are outlined below. In each reaction box enter a single letter designating the best reagent and conditions selected from the list at the bottom of the page. CH2 – Br First Step CH2 – CH2 – NH2 A. Second Step O O First Step C – CH3 CH2 – N B. H Second Step CH2CH3 Third Step C. N–H First Step N N(CH3)2 Second Step N NO2 First Step | H D. Second Step First Step E. Br Second Step Third Step Fourth Step (a) (i) LiAlH 4 in ether (ii) H 2O & base (b) C 2H 5NH 2(cat. H(+) ) (c) NaCN in alcohol (d) H 2 & Ni catalyst or H 2 & Pd catalyst (e) NaN 3 in alcohol (f) (CH 3CO)2 O & pyridine (g) C 2H 5Br https://t.me/studyzee

493 O (h) , Hr (i) 2CH 3I & pyridine (j) KOH in H 2O ANSWERS — LEVEL 2 1. A – c, a or c, d; B – b, d, f; C – h, d; D – d, i or a, i; E – e, a, h, a https://t.me/studyzee

494 11 CARBENE AND NITRENE Level - 1 OH NH2 1. O ¾B¾r2¾KO¾H ® product; (a-hydroxy amide) Product of this Hoffmann bromamide reaction is : O (b) Ph – CHO (c) Ph – CH OH (d) Ph - CH 2 - NH 2 || NO2 (a) Ph - C - CH 3 OO 2. HO NH2 ¾K¾OB¾r ® ( A) ¾¾®(B). Compound (B) is : D O C – NH (a) NH – C – H (b) || (c) NH CH3 O NH2 O O (d) O https://t.me/studyzee

O 495 || O CH2 – C – NH 2 O 3. ¾K¾OB¾r ® ( A); Product (A) is : C – O – CH3 O NH (d) O (c) O O NH (a) (b) O O Me O C OH N 4. ¾H¾2S¾O¾4 ® Product and name of the reaction is : OO NH – C – Me NH – C – Me (Hoffmann (Beckmann (a) bromamide reaction) (b) rearrangement) CN (c) (Curtius reaction) (d) None of these 5. ( X )C 4H7 OCl ¾ N¾H¾3 ® C 4H 9ON ¾B¾¾r2 ® CH 3CH 2CH 2NH 2 ; Compound (X) is : KOH O O CH3 || C – Cl (c) OH (a) (b) Cl (d) Cl CHO Cl CH3 6. Which of the following will not give Hoffmann bromamide reaction ? O O || || (a) CH 3 - C - NH 2 (b) Ph - C - NH 2 O O || || (c) CH 3 - C - NH - Br (d) Ph - C - NH - Ph OH OH 7. + ( x) ¾((21)¾)HNr¾aOH® O; Reactant x is : (a) CH 3Cl (b) CH 2Cl 2 (c) CHCl 3 (d) CCl 4 https://t.me/studyzee

496 18 – H 8. N O C ¾H¾2S¾O¾4 ®( A). Product (A) of the reaction is : H 2O18 O O18 || || (a) Ph - NH - C - Ph (b) Ph - NH - C - P h OH (d) Ph - CH 2 - NH - Ph | (c) (Ph)2 -C - NH 2 CH3 Ph Ph CH3 C C ¾H¾2S¾O¾4 ® (B) 9. .. N ¾H¾2S¾O¾4 ® ( A), .. N OH OH Product (A) & (B) respectively in the above reaction are : OO OO || || || || (a) Ph - C - NH - CH 3, Ph - C - NH - CH 3 (b) CH 3 - C - NH - Ph, CH 3 - C - NH - Ph OO OO || || || || (c) Ph - C - NH - CH 3, CH 3 - C - NH - Ph (d) CH 3 - C - NH - Ph, Ph - C - NH - CH 3 10. NBS ¾K¾OB¾r ® (A) . Product (A) is : O O O (d) O OH O- (c) O NH (a) NH2 (b) NH2 O O Ph O ¾N¾aO¾B¾r ® ( A) ; Product of the reaction is : NH2 11. CH3 (major) H Ph Ph (a) CH3 NH2 (b) CH3 H H NH2 CH3 Ph O (c) Ph H (d) CH3 C – O- NH H https://t.me/studyzee

497 OH 12. ¾(1(¾2) )CH¾HrC¾l3 /¾Na¾OH® ( A) (Major) OCH3 OH OH O OH Product (A) is : OH (a) O (b) O (c) OH (d) OH OCH3 OCH3 OCH3 OCH3 O O || 13. R - C - NH 2 + xNaOH + Br2 ¾¾® R - NH 2 + 2NaBr + Na 2CO 3 + H 2O Number of moles of NaOH used in above Hoffmann bromamide reaction is : (a) 3 (b) 4 (c) 5 (d) 6 R 14. C = N , Rate of reaction toward Beckmann rearrangement H when g = CH 3CO - , Cl - CH 2 - CO - , Ph - SO - 2 2 3 (i) (ii) (iii) (a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii) (c) (iii) > (ii) > (i) (d) (iii) > (i) > (ii) 15. When primary amine reacts with chloroform in ethanolic KOH, then product is : (a) an isocyanide (b) an aldehyde (c) a cyanide (d) an alcohol 16. The reaction of chloroform with alcoholic KOH and p-toluidine forms : (a) H3C CN (b) H3C NC (c) (d) H3C NHCHCl2 17. What is the product (Q) of the following reaction ? ¾C¾HF¾B¾rI ®(Q ) Cl t- BuOK Cl (a) (b) (c) (d) Cl F https://t.me/studyzee

498 CHBr2 18. ¾N¾aO¾H,¾50¾% ®( A) ; Product (A) is : D Br (a) (b) (c) (d) Br Br Br 19. Which of the following reaction, does not give chloro benzene as a product ? (a) ¾C¾HC¾l3,¾HO¾- ® (b) ¾C¾HB¾rCl¾2, H¾O¾- ® (c) ¾C¾HB¾r2C¾l, H¾O¾- ® (d) ¾C¾HF¾ClB¾r, H¾O¾- ® 20. ¾(¾3 m¾ole¾)CH¾2¾I2 ®( A) ; Compound (A) is : Zn Cu (a) (b) (c) (d) NH2 NººC 21. + CHCl 3 + xKOH ¾® x = moles of KOH consumed is : (a) 1 (b) 2 (c) 3 (d) 4 22. Heating the acyl azide in dry toluene under reflux for 3-hours give a 90% yield for a heterocyclic product. Identify the product (A). https://t.me/studyzee

499 O C—N3 ¾h¾e¾at ®( A) NH2 toluene 90% HO N (b) N — H (a) O N N HH O (d) NH NH2 (c) — NH2 C O C == C H Br 23. Å– Br 14 ¾K¾O¾C(C¾H3¾¾)3 ®( A) C == C Heat (a) C ºº C Br (b) C ºº C Br (c) C ºº C (d) C ºº C Br https://t.me/studyzee