APPENDIX A ANSWERS TO THE SELF-TESTS CHAPTER T s22p33 (c Formal charge: -1 00 Net charge-I HC=NH, Formal let charge: o ≡N-0: A-3.(a) N≡C Forma charge: 0 0-1 Net charge:-1 HC H The more stable lewis structures are H H 775 Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
APPENDIX A ANSWERS TO THE SELF-TESTS CHAPTER 1 A-1. (a) P; 1s2 2s2 2p6 3s2 3p3 (b) S2; 1s2 2s2 2p6 3s2 3p6 A-2. (a) (c) (b) A-3. (a) (b) (c) The more stable Lewis structures are A-4. (a) (b) H O C C H H H H H C N H H H (a) ( NCS b) ( ONO c) HC NH2 O HC Formal charge: NH2 0 O 0 0 Net charge: 0 O O Formal charge: 0 1 0 Net charge: 1 N NCS Formal charge: 0 0 1 Net charge: 1 ONO Formal charge: 1 1 1 Net charge: 1 HC Formal charge: NH2 Net charge: 0 1 O 0 1 N S 1 0 0 Net charge: 1 Formal charge: C 775 Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
776 APPENDIX A A-5.(a)C12H20O (c)C14H24O (d) CoHg Br B A-6.(a) has only sp-hybridized carbon atoms has only sp-hybridized carbon atoms N Bra has only one sp-hybridized carbon atom A-7 A-8. A-9.(a) H Tetrahedral Bent Tetrahedral (b) Pyramidal yes, it is polar. A-10.(a) Linear (b) Linear (c) Bent A-ll.(a) D None (b)A, (h) C A-12.H一N一C—一H Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
776 APPENDIX A A-5. (a) (c) (b) C10H22 (d) A-6. (a) (b) (c) A-7. A-8. A-9. (a) (b) A-10. (a) Linear (b) Linear (c) Bent A-11. (a)D (c) None (e) None (g) A (b) A, B (d)B (f) A, D (h) C A-12. H C N H O H N H Pyramidal; yes, it is polar. N ClCl Cl H C C O C C H H H H H H H Tetrahedral Bent Tetrahedral Trigonal planar OCN Formal charge: 1 0 0 Net charge: 1 O S2 O O O O O S2 O O O S2 has only one sp2 -hybridized carbon atom O has only sp2 -hybridized carbon atoms N Br has only sp3 -hybridized carbon atoms N Br C9H6BrN O C14H24O OH C12H20O Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
APPENDIX A 777 A-13.(a)1la;1丌 (b)9σ;2 (c)12a;4丌 (d)13σ;4丌 A-14.(a) H3C--CH=CH-CH (c) All carbons are (b)H-C≡C-CH2-CH3 B-1.(b B-2.(b)B-3.(c B-4.(d) B-5.(a)B-6.(b)B-7.(a B-8.(d) B-9.(b)B-10.(d)B-11.(b)B-12.(e) B-13.(d)B-14.(b)B-15.(d) CHAPTER 2 CH3CHCH,CH2- CH3 CH_ CHCH3 CH3 CHCHCH H Common: Isobutyl tert-Butyl Systematic: 2-Methylpropyl 1. l-Dimethylethyl A-2.(a)28(8C-C;20C-H) (b)27(9C-C;18C-H A-3.(a) Oxidized (b) Neither (c) Neither (d) Reduced H CHCH A-4.(a) CH, CHCHCHCH3 (b) Six methyl groups, three isopropyl H3 CH3 A-5.(a) 3, 4-Dimethy heptane b) (1, 2-Dimethylpropyl)cyclone Tertiary 3 A-7. (a) 1,3-Dimethylbutyl; secondary (b) 1, I-Diethylpropyl; tertiary (c) 2, 2-Diethylbutyl; primary Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
APPENDIX A 777 A-13. (a) 11 ; 1 (b) 9 ; 2 (c) 12 ; 4 (d) 13 ; 4 A-14. (a) (c) All carbons are sp2 . (b) (d) B-1. (b) B-2. (b) B-3. (c) B-4. (d) B-5. (a) B-6. (b) B-7. (a) B-8. (d) B-9. (b) B-10. (d) B-11. (b) B-12. (e) B-13. (d) B-14. (b) B-15. (d) CHAPTER 2 A-1. A-2. (a) 28 (8 CGC; 20 CGH) (b) 27(9 CGC; 18 CGH) A-3. (a) Oxidized (b) Neither (c) Neither (d) Reduced A-4. (a) (b) Six methyl groups, three isopropyl groups A-5. (a) 3,4-Dimethylheptane (b) (1,2-Dimethylpropyl)cyclohexane A-6. Primary Secondary Tertiary (a)4 3 2 (b)3 5 3 A-7. (a) 1,3-Dimethylbutyl; secondary (b) 1,1-Diethylpropyl; tertiary (c) 2,2-Diethylbutyl; primary CH3CHCHCHCH3 CH3CHCH3 CH3 CH3 CH3CHCH2 CH3 Isobutyl 2-Methylpropyl Common: Systematic: tert-Butyl 1,1-Dimethylethyl CH3C CH3 CH3 CH3CH2CH2CH2 n-Butyl Butyl Common: Systematic: CH3CH2CHCH3 sec-Butyl 1-Methylpropyl sp2 sp2 sp O C N sp3 H C C CH2 CH3 sp sp3 H3C CH CH CH3 sp3 sp2 sp3 Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
778 APPENDIX A CH A-8. CH3 CHCHCH, CH3 E C7H16 CH1+110,一7CO,+8H2O H3 A-9 △ Ⅹ 1, l-Dimethylcyclopropane A-10.(a) 4-Ethyl-3-methylheptane thyl-2,3- thylhexane (2-Methylbutyl)cyclohexane A-l1.(a) CH3 CH, CH, CH,CH,CH, CH,CH3 (c)(CH,), CHCHCH(CH:) CH (b)(CH3)CC(CH3) (d)( CH3)3CC(CH3)3 2, 2-Dimethylpentane 4-Dimethy pentane 2, 3-Dimethylpentane 3, 3-Dimethylpentane A-13. Alcohol alkene ester. ketone A-14.10.049kJ/mol B-1.(a) B-3.(d)B-4.(c) B-5.(b)B-6. B-7.(c) (c) B-9.(a)B-10.(a)B-1l.(b)B-12.(e) B-13.(d)B-14.(d) Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
A-8. A-9. A-10. (a) (c) (b) A-11. (a) CH3CH2CH2CH2CH2CH2CH2CH3 (c) (b) (CH3)3CC(CH3)3 (d) (CH3)3CC(CH3)3 A-12. A-13. Alcohol, alkene, ester, ketone A-14. 10,049 kJ/mol B-1. (a) B-2. (d) B-3. (d) B-4. (c) B-5. (b) B-6. (a) B-7. (c) B-8. (c) B-9. (a) B-10. (a) B-11. (b) B-12. (e) B-13. (d) B-14. (d) 3,3-Dimethylpentane 3-Ethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 2,2-Dimethylpentane (CH3)2CHCHCH(CH3)2 CH3 (2-Methylbutyl)cyclohexane 3-Ethyl-2,3- dimethylhexane 4-Ethyl-3-methylheptane 1,1-Dimethylcyclopropane 1,2-Dimethylcyclopropane Cyclopentane Methylcyclobutane Ethylcyclopropane CH3CHCHCH2CH3 C7H16 C7H16 11O2 7CO2 8H2O CH3 CH3 778 APPENDIX A Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
APPENDIX A 779 CHAPTER 3 A-1 Cl Cl H Cl (Eclipsed A-3.(CH3)3CCH,C(CH3)3= 2, 2, 4, 4-tetramethylpentane (CH3)3C H H HO 7.(a)C (b) A and B (c) D CH(CH3) CH H3C CH(CH3) A-9. cis-1-Ethyl-3-methylcyclohexane has the lower heat of combustion. bicyclic; CIoH Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website
APPENDIX A 779 CHAPTER 3 A-1. A-2. A-3. (CH3)3CCH2C(CH3)3 2,2,4,4-tetramethylpentane A-4. A-5. A-6. A-7. (a)C (b) A and B (c)D (d) A A-8. A-9. cis-1-Ethyl-3-methylcyclohexane has the lower heat of combustion. A-10. Tricyclic; C10H16 More stable CH(CH3)2 H CH3 H CH(CH3)2 H H3C H OH HO H OH H HO H O H CH3 H CH3 (CH3)3C H Equatorial Equatorial Axial H CH3 (CH3)3C H (Eclipsed) Cl Cl H Cl H Cl H3CCH3 H H H H Cl H Cl (a) (b) Cl H Cl Gauche Cl H H H CH3 H Anti Cl H H CH3 H H Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website
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
