Question

Using 1-bromobutane as a starting material show a synthesis for the following. 1-pentanol 1-phenyl-1-pentanol Starting with...

  1. Using 1-bromobutane as a starting material show a synthesis for the following.
    1. 1-pentanol
    1. 1-phenyl-1-pentanol
  2. Starting with bromobenzene show a synthesis of each compound below.
    1. Benzyl alcohol
    1. 1-phenyl-1-hexanol
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Answer #1

a] CH3-CH2-CH2-CH2-Br ------------[Mg/THF]---> CH3-CH2-CH2-CH2-Mg-Br -------[ HCHO / H3O+]---->

CH3-CH2-CH2-CH2-CH2-OH

here Mg/THF and HCHO/ H3O+ are reagents used

b] Benzene + CH3-CH2-CH2-CH2-Br-------(Fe/AlCl3)--->Ph-CH2-CH2-CH2-CH2-Br -----(HCHO/H3O+)--> Ph-(CH2)5--OH

a] Ph-Br ---------[ dry Mg/ Ether]---> Ph---Mg--Br

----------[ HCHO / H2O ]---> Ph-CH2-OH

b] Ph-Br ---(Mg/ether)--> Ph-Mg-Br + CH3-(CH2)4-CHO -----(H3O+)---> Ph--(CH2)5-CH2-OH

the reagents written in brackets between arrow.

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