TNS Se LEVEL 2 Single and Multiple-choice Type 1. Which of the following shows greater reactivity towards $42 reaction than CH,—CH,Br with sodium methoxide? (@) CH-O-CHBr wr Gp. (© CH=CH-Br (a) CH=CH-CHBr Consider the $y1solvolysis of the following halides in aqueous formic acid? We ar Br CH ; , @ BSS cu-crrcn « Br (ii) Calle CHC Br Which one of the following is correct sequence of the halides, given above, in the decreas- ngayon ager 0) isivsiei (0) i>ii>iti>iv (d) ili>i> ii>iv 3. The correct statement for the given reaction is Nal CFyCOsH ‘eeione” A> B CH is optically inactive due to external compensation (©) Bis optically inactive due to internal compensation (6) Ais predominantely cis-alkene (a) Bdoes not have chiral centres (Dil. OH _ CH CHS > Product, product is 4 CHCHSH ethylene oxide” ty Product Gi) 0 (a) CH,-CH,-S-CH,-CH,-OH () CH,CH @_~ CH-OH (©) CH-CH,-O-CH-CH,-OH @ cae s< | ° CHy 5. Which of the following statements are correct? (a) The Su1 reaction obeys the Ist order kinetics (©) The solvolysis of ethylbromide in ethanoic solution is first order kinetics (©) Reonfiguration of a compound may resultir R and S configurations in an $2 reaction (d) 1-Bromo-1-phenylethane shows greater reactivity towards Syl and 2 reaction com- pared to isopropyl bromideFED) cron 6. Which of the following reactions will proceed with retention of configuration only (no inversion) at the chiral carbon? 9° HC 40 1,0. C. (b) }C-CH)-S-CH: MP @ Cae ) Be) be ; “Hs H,0. 0. (c) CH3-C-Br = d) Hs Br 25> ©) Cite SBS (@) Calte C-Br RBS CoHs Gals 7. Correct statements is (a) Nucleophilicity of SH is greater than OH in dimethyl formamide (b) Hydrazine is a better nucleophile than NH, (©). Phenoxide ion is more basic than acetate ion (d) CH, isa better nucleophile than OH in a non-polar solvent a 8 ‘ae _oH 5 A, Acanbe Ovo @ NONE Ny Vn Oo oO NO»: NO} . ©) CHO (o) ‘CHO oO OH 9, Identify the compounds that will undergo substitution reaction faster than C,H,Br with OH-/DMSO. (a) CH,CH,-S-CH,CH,Br (b) CH-CH,CH,Br (© CHy—CH—C-0 (@) CHy-CH-CH, 10. In which of the following cases, the configuration of chiral C is retained in product? Et Et (Na le oy TSC Yai * b ON CHB ©) HOH cH ON D Calls ca i BE Aion O80 wt (brs (ii) CH3O-Na* (ii) CHN2TNS Se (excess) a 1 EiMBE, (y) HSO, (gy _OBrIIKONIOH , 6, products Band Care oO 30" A (ii) H30" HO a, HO oy ~ 6 A 0 “PN ofS 12. Which statement is/are correct in the following statements? (a) Allyl bromide gives $y! reaction but vinyl chloride does not. (b) Primary alkyl halides can give Sy1 or Sy2:eaction. This depends on the structure of the substrate and nature of solvent. (©) CH,-CH=CH-CH.CI reacts with KCN to give mixture of two isomeric products. (d) CH-CH,-O-CH,Br is less reactive than tert. butyl bromide for Sy1 reaction. 13. Identify reaction that follows Sy2path @) S—o8a+ SH (b) NalAcetone + >—cl —> 1 © wast DMSO, (€) Nan + \\1 DME 14. Which of the reactions give the correct product? C1 OC; a) —. Foran “CY \CaHs_ (possible product) "cots ococn wossible produ OCHS & 1 eH,0H mn A (possible product) McOH (najot product ) me MeOH, Bun jor product) a OMe 15, Which of the following alcubwl gives Ue white luibidily imunediately with HCl + ZaCl, (anhy)? mh Ko cits —¢ 00s \w mech on win CH (d) CH,-CH,CH,OH xX POEXIST 16. A. CH,CHO + 2HCOOH + CH,COOH. The structure of Ais CH; CHy i chy-cH-0n i ad ip Gon 5° @ Grom & § © GOH (2) noneotthese <0 cin i Cron i duo i co cu,0n 17. Which of the following gives turbidity immediately with Lucas-reagent (anhy. ZnCl, + HCD? ies sie oer, on \wericr-on \orie{O)-¢-0H @ cHcHoH CHs CH3 CH3 18. The possible structure of the alcohol is HOH a wiry © cr HOH Oy (em 19. Identify correct reactivity order for $.2 reaction oO wtoas JA, © lg, cy cl cl ch SS SS Wh - of) - aa ot NO» Tn ome 20, Identify correct reactivity order for $2 reaction ct cl cl ‘Br > ©) cL cN : a br me © NO» NO»21. 23. 24, ALKYL HALIDES ALCOWOLS AND ETHERS Identify correct reactivity order for ArSN reaction qa Br cl ca ON @ > 6) . NOz NOz NO NOz ca cl ON, nN. NOz © (@) (@)and (b) are correct, NO> Nos Identify correct reactivity order for ArSN reaction a a A as oT oO NO} NO} (b) ii>i> (©) i> iii> ii (d) iii> iii Identify correct reactivity order for ArSN reaction a cl a ON 0 oy Gi) ON Nox NO? (a) i>ii> iti (b) >it: (©) i> iii> ii (a) iit>i Identify correct reactivity order for ArSN reaction F cl @ Q Gi) CO (iti) T i NO; NO; (a) i>ii>iti (b) ii>ii>i (9) i>iti> it (a) iti>[ED] curren ron 25, Identify correct reactivity order for ArSN reaction F a Br ON WC. Hc 0 «i (i) NO; cH NO; (a) i>ii>iti —(b) i> iti>i (©) i>iti> i (@) iti>i> it 26. Identify correct reactivity order for ArSN reaction F ol Br ON ON On. ” w) (ayy NO» NO» No2 (a) i>ii> (©) i>iii> (b) ii>iti> (d) iti>i>i 27. Identify correct reactivity order for ArSN reaction F cl br ON Wye. (i) Gi) (iii) ON NOp No. Hy (a) i>ii>iti (b) ii>iti>i (© idiii @ 28, Identify correct nucleophilicity order on @ ok i) Sa (iii) + < (a) i>ii>itt (b) ii>iti>i (©) i>iti> (a) >i 29, Identify correct nucleophilicity order N. N. o [4 wo 4 (ii) A A ©) (a) i>ii>ii ii>iti>i (©) i>ii> it (a) it30. 31. 32, 33. Identify correct nucleophilicity order NO? "Oa 7 Identify correct nucleophilicity order XS i © { fi) Ns 2 wi (a) i> >a (0) i>iii> ii Identify correct nucleophilicity order @ HO (i) HS (a) i>ii>iii (©) i>iti> ii Identify correct nucleophilicity order ( PH, (i) NH, (a) i> ii> iii (©) i>iti L. Identify correct nucleophilicity order we ee U U (a) i>ii>iii (©) i>iii>ii ©) (@) (b) (a) (b) (a) ) (d) (b) (a) ee TTS fi fii it u>am>a iii>i> ii (iii) Hse i> iti>i iil>ii>i Gi) ASH, fi iti>i Se Gi) AQ | A fi>iii>i iii>it>i 38. Identify correct reactivity order for Syl reaction[EQ] curren rovn 36, Identify ccorrect reactivity order for Sy1 reaction’ wae em Lg hos cl) te GO te © > @ > U OMe b OA CHy 37. Identify final product in following sequence © @) NH °CHs C HN. cH OC Ona 38, Identify final product of following action oO ° e A LAX ao, Ls @ 6 i I 6 eK ° ar, mc

48, (ii) Mg, THE then H)C-O, then H30* (iii) HyO*, heat ; (a) ‘CH ; ° Oo ‘Br (ii) CHpIp, Zn-Cu on ° fa) OQ (b) (©) (d)(ED) crurten rove oH go, BYMe-(CH)y-MgBr, cer then H30* 3 BL q C L (a) (b) (©) (a) AAS ¥ oN oS cucu cuculs Br ir s. 22 HBr BH HBr Br] CHs CH (50:50 of these enantiomers) @ x o\_/ © Sy @ rv 52, Os (LDA CO Gi) CHsI (ii) NaBHy/MeOH 0 OH OH (@) one, ©) o © Or @ o 5a NL HB ark, ND) " (i PIIGP, then rDult iiy (a) on (b) or on NS NZALKYL HALIDES ALCOWOLS AND ETHERS 54 CO () (CH3CO),O/AICIs ° 2 (ii) Zn/Hg. HCL (iii) CHYCVAICH "APO OS 55. HH CO;CH;CHy (i) LiAIM, then H30* (Gii) Hs0/heat ° @ wo, ot OH OH aA (@ onc 56. Identify major product for the following reaction a eq. Nal/Acetone a ; a 1 1 a a om Oho ee OH on(EEA) curren ron Ho © oni ome ou @ oO 58. Identify major product for the following reaction a (i) Excess MeMgCl Major product is? (w) HO" HON, tb) HO oy OH © a (a) em ets 59, Identify major product for the folowing reaction ds _ Gat oh BE wor! 60. Identify major product for the following reaction or 5 Sto. Major products?ALKYL HALIDES ALCOWOLS AND ETHERS NRy @- (b) 3 a" ae NRp © CL @ : J 61. Identify major product for the following reaction 1 NaS, ajor products? Ho: ome SH SH L 1 (@) ‘ ©) ae Ho} “OMe Ho OMe SH SH a) (a) CO) 110 OMe How “OMe \Y 62. Choose the major product of the following, reaction oA, nea oon 63. Identify major product of the following reactior Cis _BHYTHF | _octry | 4 _NaCNDMF_ Thon 7 _aCHs cN AN acl cN @ ) or ol @ Q™ N cN[ED] curren ron 64. Identify best reagent for the following conversion : Lon Reagent? : oe (a) ZnCl,/HCL—(b) PCI, (©) Pcl, (@ soci, 65. Identify best reagent for the following conversion on Reagent? Cl (a) ZnCl,/HCL —(b) PCI, (©) PCL, (a) soci, 66, Identify best reagent for the following conversion HO ch, (@) ZnCl,/HCL_—(b) PCI, (© Pcl, (a) soc, 67. Identify reactions that correctly match with their products ® ~ Le (b) 4 (©) A ys (d) Aleoholie KOH AALKYL HALIDES ALCOWOLS AND ETHERS 68. Identify reactions that correctly match with their products Alcohol KOH, 0 *Y “LD prone oH ssn 2 O “Alcoholic KOH, \ 4 Aeoots Kon setter Men 69, Identify reactions that correctly match with their products ‘Yo @ Alcoholic KOH - Alcoholic KOH, smn “sta Aleshole KOM, Rate sf 0 el) menos Alcoholic KOU MesN 70. Identify reactions that correctly match with their products QO. aa SQ YN Alesttiexon, SS, f a HO,, @) Of) AlebetieKon, CHO CHO.[EEE] curren ron © YN Alcoholic KOH, SS, as Br , Aleahotic KOH OO ®NMey iS 7. ent ec reactions that correctly match with their products eee nh A Alcoholic KOM 72. Identify reactions that correctly match with their products? cl a cl a, fa) EtOH cto FO” ~O- Moncsubsttuted product cd cl © CO LOH a B00" Monosubstituted product Re FO E1OH 10) E10TNS Se @ Alcoholic KOH, | <1 cl 73. Identify major product for the following reaction cel Ph~ ph —ASUCEUSNAOH Major procuct is? HO. Cl HO. OH 9 ° @ c) © @ mn mn rnd, man 74. Identify major product for the following reaction ay ay yucous NaGH oN —Aavcous NaGH Major product is? a ca HO. ay ay oy @ ONY w) Wm on a a Ho ca cl. HO, a at ° (HO (a) HO on at 75. Identify major product for the following reaction a a SS |] MaQMelMeOHt Major product is? ON ~ ~~ “Nop ome ct MeO Meo. ) © On NO» ON NE ca Meo. © i ON NO:[EEN] crurrenrovn 76, Identify S,2 reaction which is favourable in a polar protic medium (a) NaOH + CH, -I—+ HO-CH, + Nal (b) OH-+Me ON Me — > O1-Me + Mes \ af iHy+Me—'S) >» H)N-Me+$Mey \ Me ©) (@) NH, + Me-1—> H.N-Me +H TAH ____, ———____—-+ Possible products (ii) Cone. KMn0./A Gi) a oY 9° °O © o< <> (d) CT oO v o O20 ‘Ag. NaOH TY AS MBO aj pore Gi) HA,