780 APPENDIX A A-ll. The form of the curve more closely resembles ethane than butane H H CH3 CH A-12. B-1 B-2.(b)B-3.(c)B-4.(a) B-5.(a B-8.(e) B-9.(c)B-10.(e)B-1ll.(b)B-12.(a) -13.(d)B-14.(b) CHAPTER 4 A-l. (a) trans-l-Bromo-3-methylcyclopentane (b) 2-Ethyl-4-methyl-1-hexanol CH A-2.(a) ICH, CCH, CH,CH, CH, CH CH(CH3)2 A-3.(a) Functional class: l-ethyl-3-methylbutyl alcohol (b) Functional class: 1, 1, 2-trimethylbutyl chloride ubstitutive 2-chloro-2, 3-dimethylpentane A-4. Conjugate acid CH3, gate base chaos A-5.(a) Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
A-11. The form of the curve more closely resembles ethane than butane. A-12. B-1. (d) B-2. (b) B-3. (c) B-4. (a) B-5. (c) B-6. (a) B-7. (d) B-8. (e) B-9. (c) B-10. (e) B-11. (b) B-12. (a) B-13. (d) B-14. (b) CHAPTER 4 A-1. (a) trans-1-Bromo-3-methylcyclopentane (b) 2-Ethyl-4-methyl-1-hexanol A-2. (a) (b) A-3. (a) Functional class: 1-ethyl-3-methylbutyl alcohol Substitutive: 5-methyl-3-hexanol (b) Functional class: 1,1,2-trimethylbutyl chloride Substitutive: 2-chloro-2,3-dimethylpentane A-4. Conjugate acid ; conjugate base A-5. (a) (b) CH3CH2C(CH3)2 OH CH3CH2CH2Cl CH3O CH3OH2 OH CH(CH3)2 ICH2CCH2CH2CH2CH2CH3 CH3 Cl S Potential energy Torsion angle H H H CH3 H CH3 H H H CH3 CH3 H H H H CH3 H3C H 780 APPENDIX A Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
APPENDIX A 781 A-6.(a) CH CHa CH,OH NH, (K<1) (b) CHCH A-7.(a) Three (b, c)CH, CCH, CHCH, CH,CHCHCHCH3 CH_CHCH_ CHCH3 (Least stable) CH3 A-8. CH, CCH3 Cl, CH.CCHCI HCl A-10.△H 57kJ(-13.5kcal) A-ll.(a)(CH3)3C +HBr (CH3)3C一 (CH)CCOH H,O+(CH3)C CH3)C-Br (c) Water is displaced directly from the oxonium ion of 1-butanol by bromide ion. a pri- mary carbocation is not involved CH CH, CH, CH,TOH H,O CH, CH,CH,CH, Br A-12.(a) 3-Methyl-3-pentanol (c) Fluorine(F2) (e) (b) KOC(CH3)3 (d) Ethyl radical, CH3CH B-1.(e)B-2.(c)B-3.(b)B-4.(c) B-5.(e)B-6.(c)B-7.(d)B-8.(a) B-9.(c)B-10.(d)B-11.(c)B-12.(e) B-13.(a)B-14.(c)B-15.(c)B-16.(c) Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
APPENDIX A 781 A-6. (a) (b) A-7. (a) Three (b, c) A-8. A-9. A-10. H° 57 kJ (13.5 kcal) A-11. (a) (b) (c) Water is displaced directly from the oxonium ion of 1-butanol by bromide ion. A primary carbocation is not involved. A-12. (a) 3-Methyl-3-pentanol (c) Fluorine (F2) (e) Cl2 (b) KOC(CH3)3 (d) Ethyl radical, CH3C . H2 B-1. (e) B-2. (c) B-3. (b) B-4. (c) B-5. (e) B-6. (c) B-7. (d) B-8. (a) B-9. (c) B-10. (d) B-11. (c) B-12. (e) B-13. (a) B-14. (c) B-15. (c) B-16. (c) CH3CH2CH2CH2 OH H2O CH3CH2CH2CH2Br 2 Br C H3C H3C CH3 O H H (CH3)3C Br (CH3)3C Br (CH3)3C (CH3)3C OH2 H2O (CH3)3C (CH3) OH H Br 3C Br OH2 Br2 Br Br Br HBr CH3CCH3 Cl2 CH3 CH3 CH3CCH2Cl HCl CH3 CH3 CH2CHCH2CHCH3 CH3 CH3 (Least stable) CH3CHCHCHCH3 CH3 CH3 CH3CCH2CHCH3 CH3 CH3 (Most stable) CH3CH2O NH H 2 CH3CH2O NH3 CH3CH2OH NH2 (K 1) Stronger base Stronger acid Conjugate acid Conjugate base Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
782 APPENDIX A CHAPTER 5 A-1.(a) 2, 4, 4-Trimethyl-2-pentene (c)(E)-2, 7-Dibromo-3-(2-methylpropyl)- (b)(E)-3, 5-Dimethyl-4-octene (d) 5-Methyl-4-hexen-3-o1 A-2.(a) 2. 3-Dimethyl-2-pentene 1, 6-Dimethylcyclohexene b) Isomer 5 A-4. Two spC atoms; four spC atoms; three sp2sp o bonds A-5.(a) (c) A-6. A-7. (a) H,C=CCH, CH, CH3 +(CH3),C=CHCH, CH3(major) CH (c)( CH),CHCHCH(CH3) (X=Cl, Br. D (d) H,C=CC(CH3)3 Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
CHAPTER 5 A-1. (a) 2,4,4-Trimethyl-2-pentene (c) (E)-2,7-Dibromo-3-(2-methylpropyl)- 2-heptene (b) (E)-3,5-Dimethyl-4-octene (d) 5-Methyl-4-hexen-3-ol A-2. (a) (c) (b) (d) A-3. (a) (b) Isomer 5 (c) Isomers 1 and 4 (d) Isomers 2 and 3 A-4. Two sp2 C atoms; four sp3 C atoms; three sp2 sp3 bonds A-5. (a) (c) (b) A-6. A-7. (a) (b) (c) (d) CC(CH3) H2C 3 CH3 (X Cl, Br, I) (CH3)2CHCHCH(CH3)2 X (major) CH2 CH3 CCH2CH2CH3 CHCH2CH3 (CH (major) 3) H2C 2C CH3 (Z)-3-Methyl-3-hexene (E)-3-Methyl-3-hexene Cl Cl OH 1 2 3 4 5 6 OH 4-Methyl-4-penten-2-ol 5-Chloro-2-methyl-1-hexene Cl 1,6-Dimethylcyclohexene 2,3-Dimethyl-2-pentene 782 APPENDIX A Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
APPENDIX A 783 A-8. CH CHCCHBr A-9. Step 1: Protonation H—OH Step 2: Dissociation Step 3: Deprotonation OH t Ho HH A-10. NaOCH,CH A-11 A-12. Cis isomer (CH3),CH (CH3),CH Cl Trans isomer. CH(CH3)2 (CH3)2CH The trans isomer will react faster because its most stable conformation(with the isopropyl group equatorial) has an axial Cl able to undergo E2 elimination A-13. Rearrangement(hydride migration) occurs to form a more stable carbocation HH Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
APPENDIX A 783 A-8. A-9. Step 1: Protonation Step 2: Dissociation Step 3: Deprotonation A-10. A-11. A-12. Cis isomer: Trans isomer: The trans isomer will react faster because its most stable conformation (with the isopropyl group equatorial) has an axial Cl able to undergo E2 elimination. A-13. Rearrangement (hydride migration) occurs to form a more stable carbocation. H3PO4 H OH H OH2 H H2O Cl (CH3)2CH CH(CH3)2 Cl (CH Cl 3)2CH (CH3)2CH Cl H Br CH3 CH3 Br CH3O NaOCH2CH3 CH3CH2OH Br (major) H H OH2 H3O OH2 H2O OH H OH2 OH2 CH CH2Br 3CH2C CH3 CH3 Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
784 APPENDIX A A-14 3-Ethyl-4, 4-dimethyl-2-pent B-1.(c)B-2.(c)B-3.(d)B-4.(c) B-5.(a)B-6.(b)B-7.(a)B-8.(a) B-9.(a)B-10.(d)B-11.(b)B-12.(c) B-13.(a)B-14.(c)B-15.(a) CHAPTER 6 (E)3, 4-Dimethyl- 2. 3-Dimethyl (Z)-3, 4-Dimethyl- A-2.(a)(CH3)2CCH,CH CH OH HSO,(conc A-3.(a) Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
A-14. B-1. (c) B-2. (c) B-3. (d) B-4. (c) B-5. (a) B-6. (b) B-7. (a) B-8. (a) B-9. (a) B-10. (d) B-11. (b) B-12. (c) B-13. (a) B-14. (c) B-15. (a) CHAPTER 6 A-1. Five; A-2. (a) (c) (b) HBr, peroxides (d) A-3. (a) CH3 CH3 OH CH3 OH H2SO4 (conc) heat 1. B2H6 2. H2O2, HO CH3 Br OH (CH3)2CCH2CH3 OH (Z)-3,4-Dimethyl- 2-pentene 2,3-Dimethyl- 1-pentene (E)-3,4-Dimethyl- 2-pentene 2,3-Dimethyl- 2-pentene 3,4-Dimethyl- 1-pentene B Br A 3-Ethyl-4,4-dimethyl-2-pentene 784 APPENDIX A Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website