A-16 APPENDIX 2 CHAPTER 5 5.1(b)3. 3-Dimethyl-1-butene:(c)2-methyl-2-hexene:(d)4-chloro-l-pentene;(e)4-penten-2-ol 5.3()3-Ethyl-3-hexene: (c) two carbons are sp-hybridized, six are sp-hybridized;(d) there are three sp--sp'o bonds and three sp I-Pentene 2-Methyl-l-butene 2-Methyl-2-butene 3-Methyl-1-butene 5.5CH3(CH2)7 (CH2)12CH3 5.6(b)z;(c)E;(d)E H3 CH3 5.7 CH, CH3 CH,CH3 CHCH (E)-3-Methyl-2-pentene (Z)-3-Methyl-2-pentene CH3hC=C(CH3)2 5.9 2-Methyl-2-butene(most stable)>(E)-2-pentene >(Z)-2-pentene 1-pentene(least sta 5.10 Bulky tert-butyl groups are cis to one another on each side of the double bond and cause the alkene to be highly strained and unstable H CH3 Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
A-16 APPENDIX 2 CHAPTER 5 5.1 (b) 3,3-Dimethyl-1-butene; (c) 2-methyl-2-hexene; (d) 4-chloro-1-pentene; (e) 4-penten-2-ol 5.2 5.3 (b) 3-Ethyl-3-hexene; (c) two carbons are sp2 -hybridized, six are sp3 -hybridized; (d) there are three sp2 –sp3 bonds and three sp3 –sp3 bonds. 5.4 5.5 5.6 (b) Z; (c) E; (d) E 5.7 5.8 (CH3)2CœC(CH3)2 5.9 2-Methyl-2-butene (most stable) (E)-2-pentene (Z)-2-pentene 1-pentene (least stable) 5.10 Bulky tert-butyl groups are cis to one another on each side of the double bond and cause the alkene to be highly strained and unstable. 5.11 (c) (d) CH3 1 3 2 H H H H CH3 3 2 1 CH3 CH3 CH2CH3 H C C 2-Methyl-2-pentene CH3 H CH2CH3 CH3 C C (E)-3-Methyl-2-pentene CH3 H CH2CH3 CH3 C C (Z)-3-Methyl-2-pentene CH3(CH2)7 H (CH2)12CH3 H C C 1-Pentene cis-2-Pentene trans-2-Pentene 2-Methyl-1-butene 2-Methyl-2-butene 3-Methyl-1-butene 1-Chlorocyclopentene 1 5 4 3 2 Cl 3-Chlorocyclopentene 2 3 5 1 Cl 4 5 4 3 2 1 Cl 4-Chlorocyclopentene
APPENDIX 2 A-17 H 5.12(b) Propene;(c) propene:(d)2, 3, 3-trimethyl-l-butene CI 513(b) Ma」jor Minor Minor 5.14 1-Pentene, cis-2-pentene, and trans-2-pentene H3C OH 515(b) + ho CH H3 H, 0: HCH + HO + oH OH, H Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
APPENDIX 2 A-17 (e) (f) 5.12 (b) Propene; (c) propene; (d) 2,3,3-trimethyl-1-butene 5.13 (b) (c) 5.14 1-Pentene, cis-2-pentene, and trans-2-pentene 5.15 (b) and (c) and H2O H H H H H H3O H OH2 OH3 OH H H H2O CH2 H3O H CH2 H2O H CH3 H3O CH3 H H H2O H3C OH CH3 H2O Major and H Minor CH3 Major CH2 Minor and 1 H CH3 H 5 2 3 4 H H CH3 3 2 1 5 4
A APPENDIX 2 CH3 CH3 5.16 巴H叫 CH3 5.17 (b)(CH3)2C=CH,;(c) CH3 CH=C(CH,CH3)2;(d) CH3CH=C(CH3h(major) and CH,=CHCH(CH3)(minor);(e)CH2=CHCH(CH3)2;(f)1-methylcyclohexene(major) and methylenecyclohexane(minor) 5.18 CH2=CHCH CH3, cis-CHa CH=CHCH3, and trans-CH, CH=CHCH3 CH3O CH3—>CH3O—H+H2C=C(CH3)2+:Cl 520(CH3)3C H (CH3)2C-O:、个 CHAPTER 6 6.1 2-Methyl-1-butene, 2-methyl-2-butene, and 3-methyl-1-butene 6.2 2-Methyl-2-butene(112 kJ/mol, 26.7 kcal/mol), 2-methyl-1-butene(118 kJ/mol, 28.2 kcal/mol), and 3-methyl-1-butene(126 k//mol, 30.2 kcal/mol) 6.3 (b)(CH3)2CCH- CH3 (c) CH, CHCH, CH3 (d)CH3CH2 6.4(b)(CH,3)2CCH CH, ()CH3 CHCH2CH3 (d)CH, CH2 CH 6.5 CH C-CH=CH,->CH3C--CHCH CHCH3 CH3 CI CH3 CH3C CH3C--CHCH3 CHac CH3 6.6 Addition in accordance with Markovnikov's rule gives 1, 2-dibromopropane Addition oppo- site to Markovnikov's rule gives 1, 3-dibromopropane 6.7 Absence of peroxides:() 2-bromo-2-methylbutane: (c)2-bromobutane;(d)1-bromo-l-eth ylcyclohexane. Presence of peroxides:(b)1-bromo-2-methylbutane: (c)2-bromobutane;(d)(1-bro methyl)cyclohexane Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
A-18 APPENDIX 2 5.16 5.17 (b) (CH3)2CœCH2; (c) CH3CHœC(CH2CH3)2; (d) CH3CHœC(CH3)2 (major) and CH2œCHCH(CH3)2 (minor); (e) CH2œCHCH(CH3)2; (f) 1-methylcyclohexene (major) and methylenecyclohexane (minor) 5.18 CH2œCHCH2CH3, cis-CH3CHœCHCH3, and trans-CH3CHœCHCH3. 5.19 5.20 CHAPTER 6 6.1 2-Methyl-1-butene, 2-methyl-2-butene, and 3-methyl-1-butene 6.2 2-Methyl-2-butene (112 kJ/mol, 26.7 kcal/mol), 2-methyl-1-butene (118 kJ/mol, 28.2 kcal/mol), and 3-methyl-1-butene (126 kJ/mol, 30.2 kcal/mol) 6.3 (b) (c) (d) 6.4 (b) (c) (d) 6.5 6.6 Addition in accordance with Markovnikov’s rule gives 1,2-dibromopropane. Addition opposite to Markovnikov’s rule gives 1,3-dibromopropane. 6.7 Absence of peroxides: (b) 2-bromo-2-methylbutane; (c) 2-bromobutane; (d) 1-bromo-1-ethylcyclohexane. Presence of peroxides: (b) 1-bromo-2-methylbutane; (c) 2-bromobutane; (d) (1-bromoethyl)cyclohexane. CH3C CH3 CH3 CH CH2 CH3C CH3 CH3 CHCH3 CH3C CH3 CH3Cl CHCH3 CH3C CH3 CH3 CHCH3 CH3C CH3 CH3 CHCH3 Cl HCl Cl Cl CH3 shift CH3CH2 CH 3CHCH2CH3 (CH3)2CCH2CH3 Cl CH3CHCH2CH3 CH3CH2 Cl (CH3)2CCH2CH3 Cl H (CH3)3C (CH3)3C O Br Cl CH3O H H2C C(CH3)2 CH3O H H C H C CH3 CH3 Cl CH3 CH3 H OH H H2O H CH3 H CH3 CH3 H CH3 CH3 CH3
APPENDIX 2 Cyclohexene Cyclohexyl hydrogen sulfate 6.9 The concentration of hydroxide ion is too small in acid solution to be chemically sig b when it is protonated in acid solution 6.12(b)CH,CHCH- CH3 (c) CH,OH (e)CH3 CHCH(CH_ CH3)2 (f)HOCH, CH2 CH(CH,CH3)2 6.15 2-Methyl-2-butene(most reactive)> 2-methyl-1-butene >3-methyl-1-butene(least reactive) 6.16 (b)(CH3)2C--CHCH3 (c) BrCH, CHCH(CH3) (d) Br 6.18 cis-(CH3)2CHCH,CH,CH2 CH, CH=CH(CH2) CH3 6.19 2, 4, 4-Trimethyl-l-pentene NaoH CH 6. 20 (CH3)3CBr- heat"(CH3)C=Ch2 Ho(CH3)2C-CH2Br 6.21 Hydrogenation over a metal catalyst such as platinum, palladium, or nickel CHAPTER Z Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
APPENDIX 2 A-19 6.8 6.9 The concentration of hydroxide ion is too small in acid solution to be chemically significant. 6.10 is more reactive, because it gives a tertiary carbocation when it is protonated in acid solution. 6.11 E1 6.12 (b) (c) (d) (e) (f) HOCH2CH2CH(CH2CH3)2 6.13 6.14 6.15 2-Methyl-2-butene (most reactive) 2-methyl-1-butene 3-methyl-1-butene (least reactive) 6.16 (b) (c) (d) 6.17 cis-2-Methyl-7,8-epoxyoctadecane 6.18 cis-(CH3)2CHCH2CH2CH2CH2CHœCH(CH2)9CH3 6.19 2,4,4-Trimethyl-1-pentene 6.20 6.21 Hydrogenation over a metal catalyst such as platinum, palladium, or nickel CHAPTER 7 7.1 (c) C-2 is a stereogenic center; (d) no stereogenic centers. 7.2 (c) C-2 is a stereogenic center; (d) no stereogenic centers. (CH3)3CBr (CH3)2C CH2 (CH3)2C OH CH2Br NaOCH2CH3 heat Br2 H2O Br CH3 OH BrCH2CHCH(CH3)2 OH (CH3)2C OH Br CHCH3 Br 82Br 82Br H H3C H HO H H3C CH3 CH3CHCH(CH2CH3)2 OH OH H CH2OH CH3CHCH2CH3 OH CH3 CH3 C CH2 C CH3 Cyclohexene H2SO4 OSO2OH Cyclohexyl hydrogen sulfate
APPENDIX 2 73(b)(Z-1, roethene is achiral. The plane of the molecule is a plane of symmetry. A second plane of ry is perpendicular to the plane of the molecule and bisects the carbon- carbon bond (c)cis-1, 2-Dichlorocyclopropane is achiral. It has a plane of symmetry that bisects th C-1--C-2 bond and passes through C-3 (d)trans-1, 2-Dichlorocyclopropane is chiral. It has neither a plane of symmetry nor a cen- 74[axlb-39° 7.6 (+)-2-Butanol 7.7(b)R;(c)S;(d)S H3C △ CH3 CH3 CH 9(b)FCH, (c)H CH,Br (d) CH,CH3 CHCH CH-CH 7.10S CH3 OH HO 7.11 H NH, H,N H, CHs Erythro 7122S,3R 7. 13 2, 4-Dibromopentane 7.15 RRR RRS RSR SRR SSS SSR SRS RSS 7. 17 Epoxidation of cis-2-butene gives meso-2, 3-epoxybutane: trans-2-butene gives a racemic mixture of (2R, 3R)and (2S, 3S)-2,3-epoxybutan 7.18 No. The major product cis-1, 2-dimethylcyclohexane is less stable than the minor product trans-1, 2-dimethylcyclohexane. CO,H CO,H 7.19HO CO,H CO,H 20 No .21(S)-l-Phenylethylammonium(S)-malate Forward Main Menu TOC Study Guide Toc Student OLCMHHE Website
A-20 APPENDIX 2 7.3 (b) (Z)-1,2-Dichloroethene is achiral. The plane of the molecule is a plane of symmetry. A second plane of symmetry is perpendicular to the plane of the molecule and bisects the carboncarbon bond. (c) cis-1,2-Dichlorocyclopropane is achiral. It has a plane of symmetry that bisects the C-1±C-2 bond and passes through C-3. (d) trans-1,2-Dichlorocyclopropane is chiral. It has neither a plane of symmetry nor a center of symmetry. 7.4 []D 39° 7.5 Two-thirds (66.7%) 7.6 ()-2-Butanol 7.7 (b) R; (c) S; (d) S 7.8 (b) 7.9 (b) (c) (d) 7.10 S 7.11 7.12 2S,3R 7.13 2,4-Dibromopentane 7.14 cis-1,3-Dimethylcyclohexane 7.15 RRR RRS RSR SRR SSS SSR SRS RSS 7.16 Eight 7.17 Epoxidation of cis-2-butene gives meso-2,3-epoxybutane; trans-2-butene gives a racemic mixture of (2R,3R) and (2S,3S)-2,3-epoxybutane. 7.18 No. The major product cis-1,2-dimethylcyclohexane is less stable than the minor product trans-1,2-dimethylcyclohexane. 7.19 7.20 No 7.21 (S)-1-Phenylethylammonium (S)-malate H OH H OH CO2H CO2H HO H OH H CO2H CO2H and S S R S Erythro H OH H NH2 CH3 CH3 Erythro HO H H2N H CH3 CH3 Threo HO H NH2 H CH3 CH3 Threo H2N H OH H CH3 CH3 H OH CH CH2 CH3 H CH2Br CH3 CH2CH3 FCH2 H CH3 CH2CH3 F F H3C H