790 APPENDIX A A-9. Dissociation to give a secondary carbocation CHaCH,CH,CHCH(CH3)2- CH,CH,CH, CHCH(CH3)2 Rearrangement by hydride migration to give a tertiary carbocation CH3 CHC(CH3)2 CH CH, CH, CH,C(CH3)2 H Capture of the carbocation by water to give product CH, CH_CH, CH, C(CH )+ OH -(-H) CHaCH, CH,CH,C(CH3) B-1.(b)B-2.(c)B-3.(d)B-4.(c) B5.(d)B-6.(a)B-7.(c)B8. B-9.(c)B-10.(a)B-11.(a) B-13.(c)B-14.(c) CHAPTER 9 A-1. (a)4,5-Dimethyl-2-hexyne (c) 6. 6-Dimethylcyclodecyne (b) 4-Ethyl-3-propyl-1-heptyne A-2.(a) (e)(CH3)2CHC≡CH CHa CH,CH,C (b) CH,CH,CH, CCH ()Na,NH3() C Cl (c) H,O, H,SO4. HgSO CH,CH3 H3C (h) CH- CH_ H CH3 CH2CO2H A-3. Reaction(2)is effective; the desired product is formed by an SN2 reaction. CH3CH2CHC≡CNa+CHI CH2CH2CHC≡CCH3+Nal Reaction(1)is not effective, owing to E2 elimination from the secondary bromide CH3CH2CHCH3+CHC≡CN CH CHECHO CH2C≡CH+NaBr Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
A-9. Dissociation to give a secondary carbocation Rearrangement by hydride migration to give a tertiary carbocation Capture of the carbocation by water to give product B-1. (b) B-2. (c) B-3. (d) B-4. (c) B-5. (d) B-6. (a) B-7. (c) B-8. (d) B-9. (c) B-10. (a) B-11. (a) B-12. (c) B-13. (c) B-14. (c) CHAPTER 9 A-1. (a) 4,5-Dimethyl-2-hexyne (c) 6,6-Dimethylcyclodecyne (b) 4-Ethyl-3-propyl-1-heptyne A-2. (a) (e) (b) (f) Na, NH3(l) (c) H2O, H2SO4, HgSO4 (g) (d) (h) A-3. Reaction (2) is effective; the desired product is formed by an SN2 reaction. Reaction (1) is not effective, owing to E2 elimination from the secondary bromide. CH NaBr CH 3C CNa 3CH2CHCH3 Br CH3CH CHCH3 CH3C CH CH3 CH I NaI 3CH2CHC CH3 CNa CH3CH2CHC CH3 CCH3 CH3CH2CH2CHCO2H CH3CH2CO2H CH3 C C H H3C CH3 H C C Cl H3C Cl CH2CH3 CH3CH2CH2CCH3 Cl Cl (CH3)2CHC CH CH3CH2CH2C Cl CH2 CH3CH2CH2CH2C(CH3)2 CH3CH2CH2CH2C(CH3)2 OH (H) OH2 CH3CH2CH2CH2C(CH3)2 CH3CH2CH2CHC(CH3)2 H CH3CH2CH2CHCH(CH3)2 CH3CH2CH2CHCH(CH3)2 Br 790 APPENDIX A Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
APPENDIX A 791 A-4.(a)CH,CH,BrDMSO.H,C-CH, BrCH,CH, Br BrCH,CH,I2,Hc=cn面C=cHH NaNI CHCH, Br HC≡ CCHCH C≡CCH,CI CH3CH2C≡CCH2CH aNH. N HC=CHCH.CH ICH, CH3 2.h.O HCCCH,CH As in part(b) CHCH2C≡CCH2CH3 NaNH (d)HC≡CH HC≡CNa HC≡CCH2CH(CH3)2 HCECCH, CH(CH3)2 CH, CCH, CH(CH3), HC CHaCH, CH,CH3 (E)-2-Heptene A-6.(CH3)CC≡CH (CH3)2CC≡C:Na CHI CH,CH,OH CHCH,CH, Br C A-7.E:HC≡CCH2CH3F:CHCH2C≡CCH2CH A-8. H Lindlar pd CH=CH.B, CHCHOH 2.H-O, HO B-1.(a)B-2.(c)B-3.(a)B-4.(d) B-5.(b)B-6.(b)B-7.(e)B-8.(c B-9.(b)B-10.(a)B-1ll.(d)B-12.(b) Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
APPENDIX A 791 A-4. (a) (b) (c) (d) A-5. A-6. A-7. A-8. B-1. (a) B-2. (c) B-3. (a) B-4. (d) B-5. (b) B-6. (b) B-7. (e) B-8. (c) B-9. (b) B-10. (a) B-11. (d) B-12. (b) C CH CH CH2 CH2CH2OH H2 Lindlar Pd 1. B2H6 2. H2O2, HO E: HC CCH2CH3 F: CH3CH2C CCH2CH3 CH3CH2CH2Br D CH3CH2CH2OH C C Na (CH3)3CC B (CH3)3CC CH A C C H H3C CH2CH2CH2CH3 H (E)-2-Heptene CCH2CH(CH3) HC 2 H2O, H2SO4 HgSO4 CH3CCH2CH(CH3)2 O HC CH HC CNa CCH2CH(CH3) HC 2 NaNH2 (CH3)2CHCH2Br HC CCH2CH3 As in part (b) CH3CH2C CCH2CH3 H2C CHCH2CH3 ClCH2CHCH2CH3 Cl2 1. 3NaNH2, NH3 2. H2O HC CCH2CH3 Cl HC CCH2CH3 NaC CCH2CH3 NaNH2 CH3CH2Br CH3CH2C CCH2CH3 BrCH2CH2Br HC CH HC CCH2CH3 1. NaNH2, NH3 2. H2O 1. NaNH2 2. CH3CH2Br CH3CH2Br BrCH H2C CH2 2CH2Br Br KOC(CH3 2 )3 DMSO Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website