1559T_ch07-113-13110/22/0520:20Pa9e125 ⊕ EQA Solutions to Problems.125 (c)Not at all.No appreciable reaction the solvent (d)Well.An"intramolecular"(internal)SxI reaction. (e)Well,eventually.but very.very slowly. (f)Well. (g)Well. (h)Not at all.No reaction because of the very poor nucleophile (i)Not at all.No reaction. (j)Not at all.No reaction because of the very poor leaving group. (k)Poorly.(CH3)2CHCH2CHzOCH2CH,forms also. (Poorly.Good nucleophile gives mainly CH,CH-CHCH2OCHCH 44.()CH,CH,CH,CH,CH,CH,CHBrCH,CH.CH.CHICH (b)CH,CHCHCH,some CH.CH.CH,CH,CCH,CH.CH,CH (CH.CH,CIo CH,OH:then (CH),CH (CHa)(CHa)COCHa Br OH (e)From (d). H:0 (Sx1) A better method will be presented in Chapter 8. (f)Na2S in alcohol: CBr CH2 CH2 Four SN2 displacements! GBr 45.(a)Rate =RBr].=k(0.1).and -C(CH3)2-OH (ROH). (b)New"410-3s.Addition of LiCl increases the polarity of the solution by adding ions,and this speeds up the rate-determining ionization step in the solvolysis process (c) Not at all. No appreciable reaction besides SN1 with the solvent. (d) Well. An “intramolecular” (internal) SN1 reaction. (e) Well, eventually, but very, very slowly. (f ) Well. (g) Well. (h) Not at all. No reaction because of the very poor nucleophile. (i) Not at all. No reaction. (j) Not at all. No reaction because of the very poor leaving group. (k) Poorly. (CH3)2CHCH2CH2OCH2CH3 forms also. (l) Poorly. Good nucleophile gives mainly CH3CH2CH2CH2OCH2CH3. 44. (a) (b) (c) (d) (e) From (d), A better method will be presented in Chapter 8. (f ) Na2S in alcohol: 45. (a) Rate k[RBr], so 2 104 k(0.1), and therefore k 2 103 s 1 . Product is (b) New “kLiCl” 4 103 s 1 . Addition of LiCl increases the polarity of the solution by adding ions, and this speeds up the rate-determining ionization step in the solvolysis process. C(CH3)2 OH (ROH). CH2 CH2 CH2 CH2 S2 S2 Br Br CH2 CH2 Four SN2 displacements! Br Br Br H2O (SN1) OH Br Br2, hv KOCH2CH3, CH3CH2OH CH4 CH3Cl CH3OH; then (CH3)3CH (CH3)3CBr (CH3)3COCH3 Cl2, hv KOH, H2O Br2,  CH3OH CH3CH2CH2CH3 some CH3CH2CH2CH2Cl CH3CH2CH2CH2I Cl2, hv NaI, acetone CH3CH2CH2CH3 CH3CH2CHBrCH3 CH3CH2CHICH3 Br2,  KI, DMSO Solutions to Problems • 125 1559T_ch07_113-131 10/22/05 20:20 Page 125