(A Unit of NSPIRA Management Services PVT.LTD) DPP-11 Alcohol 1. Which of the following is a secondary alcohol? OH xX @ -on Magra, © Chou (@) CHOH 2. What is the product of the following reaction? lone _80ch_, Pyridine gel Cl (a) oO + enantiomer (b) ka Cl © ‘Oo + O @ cr optically active 3. What is the major product formed in the following synthesis? 1. PBry OH 2.CH,COONa , 2.CHsCOONa_ cH,COOHOCOCH, (@ “Che w) Cc Br oO “OO . Which is not a likely product formed when the following alcohol is treated with sulfuric acid? Kou Tr 8 8 oo . What are the products of the following reaction? A — B82 Product + Enantiomer Naot HO OH HO. a) a ©) xe © SS @ ate OH OH Ho" “OH OH . What is the product of the following reaction? (a) CH,CHO (b) CHjCH,0H (© CH,CHy (4) noreaction 3. Which of the following compounds does not give a tertiary alcohol upon reaction with methylmagnesium bromide? (a) 3-methylpentanal (b) ethyl benzoate (©) 4,4-dimethylcyclohexanone (@) 4-heptanone 14. Which of the following compounds gives a secondary alcohol upon reaction with methylmagnesium bromide? Assume the usual acid workup. (a) butyl formate —_(b)_3-pentanone (©) pentanal (d@_ methyl butanoate OH on v o~15. Which of the following compounds is not oxidized by pyridinium chlorochromate (PCC)? (a) 2-methyl-2-butanol (b) L-pentanol (© 2pentanol (@)_1,3-propanediol 16. What is the major product of the following reaction? ak 1. NaBH, MeOH 2 Dilute'tid, heat 7 ‘on 2 Piuteacd heat, oO 9 @) Aa, o) AS © CO @ Ci 17. Which of the following is an allylic alcohol? (a) CH; =CHCH,0CH, = (b). CH, = CHCH2CH3, (©) HOCH =CHCH,CH; =(d) CH;CH=CHCH,OH (e) CH2 = CHCH,CH,OH 18. Give the major product of the following reaction: oO CrO5/HS04 ,_ NACN/HC, aioe product 9 9 9 @ my o) cy © @ cs ‘CN OH 19. Identify which of the compound having 2° alcohol ? @ Goa ) on © KB o> \on OH 20. Identify 2° alcohol in the given following alcohols: OH ‘OH @ nol ) D7 o (d) None of these 21. Which of the following is /are 1° alcohol? ? OH OH OH @ CY ) Cy © (@) “~~ on 22. Which of the following is sec-butyl alcohol? (a) CH,CH,CH,CH,OH (b) CH,CH(OH)CH,CH, (© (CHg)2CHCH,0H (@) (CH3),CHOH23. The isomeric alcohol which has a chiral carbon atom is: (@) n-butyl alcohol (6) iso-butyl alcohol (c) sec-butyl alcohol (d) tert-butyl alcohol 1H 24, —HSO4 (4) —S0ld KOs (8), Product (B) is: 3 (a) diastereomer (b) meso (© racemic (@)_ geometrical isomer 25. (4) He Structure of (A) is: @ ~r ) IT © >on @ all ofthese 26, Af SZ ; Structure of (A) @ naa ) © TK (@) all of these HH rE OH CH;—OH 9 27. Cy + (A) j Product (A) is: @ Cy OO) Cy © cy @ cy b-OH 28. —E, (4) ; Product (A) is: 2 of oG®) off « 29. Best method to convert alcohol to halide is: (a) ROH+SOCl,—> R—CI+SO,+HCI — (b) R—OH+PCl; —> R—Cl (© R—OH+PCls—> R—Cl (@) R—OH+HCI—> R—Cl+H,0 CH, 30. In the given reaction <> fou Gone H804 , 4 The product A OH OH CH,(a) é CH. o ° CH CH. ) =" ‘CH3 ‘CH CHy @ CH oO COOCH, 2 31. Which of the following is most reactive towards the acid-catalysed dehydration? OH H OH 7 (a) CO (b) © S @ O 32. Which of the following alcohols is least reactive towards acid-catalysed dehydration? 1H OH PH ) ‘o © So @ O OH 33. Cm is: @ A ) © eo @ OO HO CO GX OB oO 35. In which of the following reaction pair of diastereomers will form ? OH ; : @ Loni ® >/ ai, © Hk a (d) All of these @) OrsCHa I 36. CH, —C — CHCH, +HBr— "5 ?; Major product of the reaction is : CH, OH Hs te Gs (a) CH,;—C—CHCH,; —(b) CHa —C— cata | CH, CH, Br Ha Hs Hs © CHy—C—GHcH; —(@) Cty —C CHC (@) Hy —F—CHACHZCHs lo | Br CH CH,Br Br CH, 37 Cher + HBr ——» 2» Major product of the reaction is = ‘OH CH, CH ‘Br o CH a Ce Br ‘CH CHy, ‘CH3 CHy an Kot w CH w Co CH,Br Br (a) 1 (b) 0 @ Wm @ WV Vv 88. Which of the following alcohols dehydrates most readily ? OH o cas—{_)—on @ a Chou m™ @l () O ( mW @ WV Ov Q ‘OH Ww) “on 739. Which of the following alcohols gives a rearranged carbocation when dehydrated? CH, CHy OH OH | CH,CHCH, CH3CHCH CH, or Hye—¢— On | | OH OH CHy oO a a aw) ™) (aI () 0 @ mW @) Vv Vv heat CHA OH Hs 40. C3 —HECL, >, Major product of the reaction is : CH, CH, CH, CH, CH, “O DB ©QO OD 0A 41. Which of the following reagents can be used to oxidize 1° alcohols to aldehydes ? (@) KMn0, (b) MnO, (© K,Cr,0, (d@) H,0, (e) Pcc 42. In the chromic acid oxidation of alcohols, the chromium is: (a) reduced from Cr“ tocr*? (b) oxidized fromcr*® tocr*? (©) reduced fromCr* toCr*® (a) oxidized fromCr*? tocr*® (©) none of the above 43. When the optically active alcohol given below is oxidized by HCrO ,, the major product is QOH ICH (a) a ketone which is meso and optically inactive (b) an optically active ketone (© a racemic mixture of ketones which is optically inactive (@ an aldehyde which is meso and optically active (©) an acyclic carboxylic acid 44. Which of the following compound contains most acidic hydrogen ? @ HC=cH (b) CH,OH (© NHg (d) H»C =CH, 45. Which of the following compound will evolve H . gas with Na ? (@) H,C=CH, — (b) R-O—R (© R—CHy (@) R—O—HQ co,c° OH 46. Br ts 8) (apis: (a) Br cooH (b) Br-~cHo H N—CrO,Cr CH CoHip, Hevotcrs) 47, ON, P. He(OCCHs)2 5 ; Product of the reaction is: ‘CH, i) NaBD, oD oH /OH CHD i C cai @ ‘CH, CH 48. The alcohol, which would not generate a carbonyl compound on oxidation with acidified KMn0O ,, is: | (a) CH;—C—OD (b) | OH OH CH: @ CL ) CKor" © Ko @ cr ‘CH, OH 1 49. ee @) 8S, @) APL, (©); Product (©) is: IH (a) CO (b) qo (©) (dd) 50. ©, A, major product A is: @ Oo ) cr © ar @ CrOH 51. CA, —_, Major product of the reaction is: 2 9 @ ra, ) a, © (@ None of these CH. Is 52. CH3CH ,CH,OH 5 (4) SE-KOH, (gy HBF, (¢) Ms, (D), (D) is: (a) CH, —CH, —CH—NH, (b) CH, — CH —CH, mi H CHs (© CH3— 7 —NHy, (@) CH; —C —NH, _ br, 53. What is the product of the following reaction? Laie TH —rmon Ho,” O OH a Ae 4 EERE OH © or @ co CH, 54. Ht oH (4) 4 (B), Product (B) is: i SN CHy CH; (a) H——Ph (b) Hah OCH, Ph Ph Ph () H-+—0—cH, @ cro—}—a CHy CHPh Fe 55. Ph. cH, 4 (A); Product (A) is : 1H OH Pho CH; 0 Q CH, Il cu,b_<-on il > @ ph—c—c—cH, (b) CHs~¢ © Ph Cis @ CH CH Ph 56. Which of the following alcohols is oxidized to a ketone by chromic acid ? OH OH @ or “i cr i" CH,OH CH,OH C—CH, oom oT" eo OL (@) i (>) ii © if @ iv ©v Ht O—- 57. Cko —HL ? , Product of the reaction is: O— HO. O HO. OH OH @ Cho ) Cr © wr @ or 58. Which of the following products is formed in good yields by the reduction of methyl 4-oxo-hexanoate (M) with NaBH 4? 9° As Me oO (a) Methyl 4-hydroxyhexanoate (b) 6-Hydroxy-3-hexanone (©) 1,4-Hexanediol (d) 4-Hydroxyhexanal 1. pce 0: OH 7 59. Mey _2NiyPH=4 5. product of the reaction is: 0. NH HN. ZNH 7 [oad © oes Oo (b) @ uw NH, 260. 61. 62. 63. 64. What is the product formed when the following lactone is treated with aqueous sodium hydroxide solution? HO OH OH @ ‘0 (b) ° OH © po @ ot Ox OH a oF In the above given compound how many functional groups are reduced by LAH (Lithium aluminium hydride) and SBH (Sodium borohydride) respectively ? (a) 4,4 (b) 4,3 (©) 3,4 @) 4,2 Which of the following alcohol will give turbidity of alkyl chloride immediately at room temperature when reacts with Lucas reagent? OH OH @~e wt © @ oo OH In which of the reaction rearrangement take place with change in carbon skeleton ? CHy | * ¥ * (a) CHy—C—cHcH, ® ~Aon_t! 1H OH é ; o Cy @ Allof these oH ~K-; Aw ow) >on to Sum of a-hydrogen in (A+B+C=?) (a) 17 ) 18 © 19 @ 20OH 6s. Cyst Major; Cte , Sum of a-hydrogen in (A+B =?) (a) 18 (®) 19 (© 20 HH OH ¢ it 66. +a; Sw: Sum of a-hydrogen in (A+B =?) (a) 15 (b) 16 © 17 + Ht 67. Cy on CTS te® Sum of a-hydrogen in (A+B =?) (a) 12 (b) 13 © 14 + Ht i >g, >< @) OH OH Cte , O20 Sum of a-hydrogen in A+B+C+D is : (a) 34 (b) 35 (© 36 OH @ . : 69. O CO ; Reagent (A) is : @ e (a) H,0 (b) Ht/A (©) HO (d) 21 (d) 18 (d) 15 (d) 37 ° (@) NH,How many moles of HI consumed in above reaction ? (a) 1 (b) 2 © 3 qd) 4 27. Compare rate of reaction with OH™ : @ oO’ wi fo Gi) oO (a) i>ii>iii (b) i>iii>ii (©) iti>ii>i (d) ii>i>iii 28, PhMgBr +Et —O —Et—> ; Product is: (diethyl ether) (a)Ph — OEt (b) Ph—OH (c) Ph—Et (d) no reaction Answers TEM Alcohols 1 Jml2fo@lale 14, | (d) | 12, | (a) | 13. | (a) 21. | @) | 22.| (0) | 23. | (e) 34. | (c) | 32. | (b) | 33. | (a) | 41. (e) | 42. | (a) | 43. | (b) 51. | (c) | 52. | (b) | 53. | (b) 61. | (d) | 62. | @) | 63. | (a) | @]s fal s Jo] Jo] e Je] s [es |e] (| 15. |(@| 16. |(@| 47. || 18 || 19. | (0)| 20. |) co] 28. /c)| 2s. || ar. || 28. || 28. |1a)| 30. | )} 35. |¢@| 36. | (e)) 37. |(0)| 38. |(@)| 39. |(a)| 40. |) | 48. || 48. |) 47. |(0)| 48. fi| 49. fie} 50. | (b)) 55. |(a| 56. | oy] 57. | ()| 58. (@)| 59. |(a)| 60. | (a) (| 65. || 66. || 67. || 68. || 6% | RERERRE A