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32.4.16: Chapter 17

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    Problem 17-1
    (a) 5-Methyl-2,4-hexanediol
    (b) 2-Methyl-4-phenyl-2-butanol
    (c) 4,4-Dimethylcyclohexanol
    (d) trans-2-Bromocyclopentanol
    (e) 4-Bromo-3-methylphenol
    (f) 2-Cyclopenten-1-ol
    Problem 17-2
    (a) Alt Text Placeholder
    (b) Alt Text Placeholder
    (c) Alt Text Placeholder
    (d) Alt Text Placeholder
    (e) Alt Text Placeholder
    (f) Alt Text Placeholder
    Problem 17-3 Hydrogen-bonding is more difficult in hindered alcohols.
    Problem 17-4
    (a) HCCH < (CH3)2CHOH < CH3OH < (CF3)2CHOH
    (b) p-Methylphenol < Phenol < p-(Trifluoromethyl)phenol
    (c) Benzyl alcohol < Phenol < p-Hydroxybenzoic acid
    Problem 17-5 The electron-withdrawing nitro group stabilizes an alkoxide ion, but the electron-donating methoxyl group destabilizes the anion.
    Problem 17-6
    (a) 2-Methyl-3-pentanol
    (b) 2-Methyl-4-phenyl-2-butanol
    (c) meso-5,6-Decanediol
    Problem 17-7
    (a) NaBH4
    (b) LiAlH4
    (c) LiAlH4
    Problem 17-8
    (a) Benzaldehyde or benzoic acid (or ester)
    (b) Acetophenone
    (c) Cyclohexanone
    (d) 2-Methylpropanal or 2-methylpropanoic acid (or ester)
    Problem 17-9
    (a) 1-Methylcyclopentanol
    (b) 1,1-Diphenylethanol
    (c) 3-Methyl-3-hexanol
    Problem 17-10
    (a) Acetone reacts first with methylmagnesium bromide, then hydronium, to produce 2-methyl-2-propanol. C H 3 C O R reacts first with 2 equivalents methylmagnesium bromide, then hydronium, to produce same product.
    (b) Cyclohexanone reacts first with methylmagnesium bromide, then hydronium, to produce 1-methylcyclohexanol.
    (c) Three ways to make 3-methyl-3-pentanol: 2-pentanone with methylmagnesium bromide, then hydronium; 2-butanone with ethylmagnesium bromide, then hydronium; alkyl acetate with two equivalents ethylmagnesium bromide, then hydronium.
    (d) Three ways to make 2-phenyl-2-butanol: propiophenone with methylmagnesium bromide, then hydronium; acetophenone with ethylmagnesium bromide, then hydronium; 2-butanone with phenylmagnesium bromide, then hydronium.
    (e) Formaldehyde reacts first with phenylmagnesium bromide, then hydronium, to make benzyl alcohol.
    (f) Formaldehyde reacts first with isopentylmagnesium bromide, then hydronium, to make 4-methyl-1-pentanol.
    Problem 17-11 Cyclohexanone + CH3CH2MgBr
    Problem 17-12 1. p-TosCl, pyridine; 2. NaCN
    Problem 17-13
    (a) 2-Methyl-2-pentene
    (b) 3-Methylcyclohexene
    (c) 1-Methylcyclohexene
    (d) 2,3-Dimethyl-2-pentene
    (e) 2-Methyl-2-pentene
    Problem 17-14
    (a) 1-Phenylethanol
    (b) 2-Methyl-1-propanol
    (c) Cyclopentanol
    Problem 17-15
    (a) Hexanoic acid, hexanal
    (b) 2-Hexanone
    (c) Hexanoic acid, no reaction
    Problem 17-16 SN2 reaction of F− on silicon with displacement of alkoxide ion.
    Problem 17-17 Protonation of 2-methylpropene gives the tert-butyl cation, which carries out an electrophilic aromatic substitution reaction.
    Problem 17-18 Disappearance of  –OH absorption; appearance of CO
    Problem 17-19
    (a) Singlet
    (b) Doublet
    (c) Triplet
    (d) Doublet
    (e) Doublet
    (f) Singlet

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