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15597.ah06_099-11210/24/0504:49 M Page104 EQA 104 chapter 6 PROPERTES AND REACTIONS OF HALOALKANES:BIMOLECULAR NUCLEOPHILIC SUBSTTTUTON 34.Answers are presented in the same manner as for Problem 32.Arrows mark electrophilic atoms. Reaction Nucleophile Substrate Leaving group Product NH: [入B sH 0 (c) 入1 (d) H CI H (e) 35.Bimolecular displacement is first order in each component. (a)Rate=A[CH CllKSCN]:2 x 10-8 mol L-'s-1 k(0.1 MX(0.1 M).so k=2x 10-L mol-'s-1. (b)The three rates are (i)4 (ii)1.20:and (ii)3.2x10-7 mol L-'s-.respectively. 36.(a)CH;CH-CHaI (b)(CHa)CHCH2CN (c)CH;OCH(CH3)2 (f)(CHa)2CHN(CHa)3*-OSO2CHs 37.(a)Starting material is R. H CH3 Product is S. CH-CH3 (b)Starting material is(,35)-2-bromo-3-chlorobutane. H (e)Starting material is(15.3R)-3-chlorocyclohexanol (the position of the OH group is understood to be C1).34. Answers are presented in the same manner as for Problem 32. Arrows mark electrophilic atoms. Reaction Nucleophile Substrate Leaving group Product (a) NH2 CH3I I CH3NH2 (b) HS Br (c) I CF3SO3 (d) N3 Cl (e) CH3Cl Cl (f) SeCN I 35. Bimolecular displacement is first order in each component. (a) Rate k[CH3Cl][KSCN]: 2 108 mol L1 s 1 k(0.1 M)(0.1 M), so k 2 106 L mol1 s 1 . (b) The three rates are (i) 4 108 ; (ii) 1.2 107 ; and (iii) 3.2 107 mol L1 s 1 , respectively. 36. (a) CH3CH2CH2I (b) (CH3)2CHCH2CN (c) CH3OCH(CH3)2 (d) CH3CH2SCH2CH3 (e) (f ) (CH3)2CHN(CH3)3 OSO2CH3 37. (a) Starting material is R. (b) Starting material is (2S,3S)-2-bromo-3-chlorobutane. (c) Starting material is (1S,3R)-3-chlorocyclohexanol (the position of the OH group is understood to be C1). CH3 CH3 Product is (2R,3R)-2,3-diiodobutane. H I I H CH3 Product is S. CH2CH3 Br H CH2Se(CH2CH3)2 Cl SeCN I H3C CH3 N CH3 N H Cl N3 H I S O O O CF3 Br SH 104 • Chapter 6 PROPERTIES AND REACTIONS OF HALOALKANES: BIMOLECULAR NUCLEOPHILIC SUBSTITUTION 1559T_ch06_099-112 10/24/05 04:49 PM Page 104