Which of the alcohols listed below would you expect to react most rapidly with PBr3?     (CH3CH2)2CH(OH)CH2CH3     CH3CH2CH2CH2CH2CH2OH     (CH3CH2)3COH     (CH3CH2)2CHOHCH3 1. (b) The conversion of 3-methyl-1-octanol to 1-bromo-3-methyloctane is best achieved through use of which of these reagents in a low temperature reaction?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section20.6: Sigmatropic Shifts
Problem 20.12P
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  1. (a) Which of the alcohols listed below would you expect to react most rapidly with PBr3?

       

    (CH3CH2)2CH(OH)CH2CH3

       

    CH3CH2CH2CH2CH2CH2OH

       

    (CH3CH2)3COH

       

    (CH3CH2)2CHOHCH3

    1. (b) The conversion of 3-methyl-1-octanol to 1-bromo-3-methyloctane is best achieved through use of which of these reagents in a low temperature reaction?

       

    Conc. HBr

       

    NaBr, H2SO4

       

    Br2

       

    PBr3

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