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15.5.11: Chapter 11

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    482465
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    Problem 11-1 (R)-1-Methylpentyl acetate, CH3CO2CH(CH3)CH2CH2CH2CH3
    Problem 11-2 (S)-2-Butanol
    Problem 11-4
    (a) 1-Iodobutane
    (b) 1-Butanol
    (c) 1-Hexyne
    (d) Butylammonium bromide
    Problem 11-5
    (a) (CH3)2N
    (b) (CH3)3N
    (c) H2S
    Problem 11-6 CH3OTos > CH3Br > (CH3)2CHCl > (CH3)3CCl
    Problem 11-7 Similar to protic solvents
    Problem 11-8 Racemic 1-ethyl-1-methylhexyl acetate
    Problem 11-9 90.1% racemization, 9.9% inversion
    Problem 11-11 H2C ═ CHCH(Br)CH3 > CH3CH(Br)CH3 > CH3CH2Br > H2C ═ CHBr
    Problem 11-12 The same allylic carbocation intermediate is formed.
    Problem 11-13
    (a) SN1
    (b) SN2
    Problem 11-15
    (a) Major: 2-methyl-2-pentene; minor: 4-methyl-2-pentene
    (b) Major: 2,3,5-trimethyl-2-hexene; minor: 2,3,5-trimethyl-3-hexene and 2-isopropyl-4-methyl-1-pentene
    (c) Major: ethylidenecyclohexane; minor: cyclohexylethylene
    Problem 11-16
    (a) 1-Bromo-3,6-dimethylheptane
    (b) 4-Bromo-1,2-dimethylcyclopentane
    Problem 11-17 (Z)-1-Bromo-1,2-diphenylethylene
    Problem 11-18 (Z)-3-Methyl-2-pentene
    Problem 11-19 Cis isomer reacts faster because the bromine is axial.
    Problem 11-20
    (a) SN2
    (b) E2
    (c) SN1
    (d) E1cB

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