11_ - P1: PCX/PBR JWDD052-11 P2: PBU JWDD052-Solomons-v2 11...

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P1: PCX/PBR P2: PBU Printer: Hamilton JWDD052-11 JWDD052-Solomons-v2 April 24, 2007 20:40 11 ALCOHOLS AND ETHERS SOLUTIONS TO PROBLEMS Note: A mixture of bond-line and condensed structural formulas is used for solutions in this chapter so as to aid your facility in using both types. 11.1 These names mix two systems of nomenclature (functional class and substitutive; see Section 4.3F). The proper names are: isopropyl alcohol (functional class) or 2-propanol (substitutive), and tert -butyl alcohol (functional class) or 2-methyl-2-propanol (substitu- tive). Names with mixed systems of nomenclature should not be used. 11.2 1-Propanol or propan-1-ol (Propyl alcohol) 1-Methoxypropane (Methyl propyl ether) 2-Methoxypropane (Isopropyl methyl ether) Ethoxyethane (Diethyl ether) 1-Butanol or butan-1-ol (Butyl alcohol) 2-Methyl-1-propanol or 2-methylpropan-1-ol (Isobutyl alcohol) 2-Methyl-2-propanol or 2-methylpropan-2-ol ( tert -Butyl alcohol) 2-Butanol or butan-2-ol ( sec -Butyl alcohol) 2-Propanol or propan-2-ol (Isopropyl alcohol) Methoxyethane (Ethyl methyl ether) (a) (b) OH OH OH O OH O O O OH OH 11.3 The presence of two OH groups in each molecule of 1,2-propanediol and 1,3-propanediol allows their molecules to form more hydrogen bonds. Greater hydrogen-bond formation means that the molecules of 1,2-propanediol and 1,3-propanediol are more highly associated, and, consequently, their boiling points are higher. 188
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P1: PCX/PBR P2: PBU Printer: Hamilton JWDD052-11 JWDD052-Solomons-v2 April 24, 2007 20:40 ALCOHOLS AND ETHERS 189 11.4 CH 3 CH 2 OH OH HO (a) (c) (b) (d) OH i, ii iii i, ii OH iii i, ii OH iii i, ii, iii 11.5 A rearrangement takes place. (a) CH 3 CH CH 2 C CH 3 CH 3 CH 3 CH CH 3 C CH 3 CH 3 + HH H O + + CH 3 CH CH 3 C CH 3 CH 3 CH 3 CH CH 3 C OH CH 3 CH 3 + 1,2-methanide shift CH 3 CH CH 3 C H O H CH 3 CH 3 + 2,3-Dimethyl-2-butanol (major product) OH 2 OH 2 (b) (1) Hg(OAc) 2 /THF-H 2 O; (2) NaBH 4 ,OH (oxymercuration-demercuration) 11.6 CH 3 CH 2 OH Stronger acid NaNH 2 Stronger base (a) + CH 3 CH 2 ONa Weaker base NH 3 Weaker acid + CH 3 CH 2 OH Stronger acid Stronger base (b) + CH 3 CH 2 ONa Weaker base Weaker acid + HC CNa HC CH CH 3 CH 2 OH Weaker acid Weaker base (c) + CH 3 CH 2 ONa Stronger base Stronger acid + NaOAc HOAc
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P1: PCX/PBR P2: PBU Printer: Hamilton JWDD052-11 JWDD052-Solomons-v2 April 24, 2007 20:40 190 ALCOHOLS AND ETHERS 11.7 (a) Tertiary alcohols react faster than secondary alcohols because they form more stable carbocations; that is, 3 rather than 2 : CH 3 O H C C CH 3 CH 3 CH 3 CX CH 3 CH 3 CH 3 CH 3 CH 3 H + + + - H 2 O X (b) CH 3 OH reacts faster than 1 alcohols because it offers less hindrance to S N 2 attack. (Recall that CH 3 OH and 1 alcohols must react through an S N 2 mechanism.) 11.8 CH 3 CCH 2 CH 3 CH 3 CH 3 CCH 2 CH 3 CH 3 Br Br - 1,2- + CH 3 CHCHCH 3 CH 3 + hydride shift CH 3 CHCHCH 3 HBr CH 3 OH + CH 3 CHCHCH 3 Br - CH 3 + OH 2 + - H 2 O 11.9 HO + HO + OTs inversion S N 2 CH 3 CH 3 C 2 H 5 C 2 H 5 HC CH (b) CH 3 C 2 H 5 + OH TsCl retention ( HCl) CH 3 C 2 H 5 ( R )-2-Butanol (a) (c) cis -4-Methyl- cyclohexanol TsCl retention Cl trans -1-Chloro-4- methylcyclohexane CH 3 Cl inversion CH 3 OH CH 3
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P1: PCX/PBR P2: PBU Printer: Hamilton
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11_ - P1: PCX/PBR JWDD052-11 P2: PBU JWDD052-Solomons-v2 11...

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