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Magazine Chapter 10: Q57P (page 540)
Show how this 1掳 alcohol can be made from the following:
(a) a 1掳 alkyl bromide
(b) formaldehyde
(c) a 7-carbon aldehyde
(d) a carboxylic acid
(e) an alkene
(f) ethylene oxide
Short Answer
Step by step solution
Primary alcohol
Primary alcohol can be easily prepared by the reaction of formaldehyde with the Grignard reagent. It is alcohol in which the hydroxy group is bonded to primary carbon atoms.
Formation of desired product
(a) Treatment of (2-bromoethyl) cyclopentane with aqueous KOH gives the desired compound. The reaction is as follows:
Formation of product in reaction a
b) Treatment of formaldehyde with (cyclopentyl methyl) magnesium bromide followed by hydrolysis gives the desired compound. The reaction is as follows:
Formation of product in reaction b
c) Treatment of 2-cyclopentylacetaldehyde with lithium aluminum hydride followed by hydrolysis gives the desired compound. The reaction is as follows:
Formation of product in reaction c
d) Treatment of 2-cyclopentylacetic acid with lithium aluminum hydride followed by hydrolysis gives the desired compound. The reaction is as follows:
e) The hydroboration of vinylcyclopentane followed by oxidation gives the desired compound. The reaction is as follows:
Formation of product in reaction e
f) Treatment of cyclopentylmagnesium bromide with oxirane followed by hydrolysis give the desired compound. The reaction is as follows:
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