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Preparation of Alcohols from Carbonyl Compounds

Which of the ...

Question

Which of the following products is formed in good yield by the reduction of methyl 4-oxo-hexanoate $(M)$ with $L i A l H_{4}$ in ether?

A

Methyl 4-hydroxyhexanoate

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B

1,4-Hexanediol

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C

4-Hydroxyhexanal

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D

6-Methoxy-3-hexanone

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Solution

The correct option is C 1,4-Hexanediol
Lithium Aluminium hydride reduces both ketone and ester group to alcohol as shown in the above image.

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Allanite wanted to prepare (R) 2-Methoxy butane using Williamson ether synthesis. He remembered that Williamson synthesis involves a

S_{N} 2

displacement, which takes place with inversion of configuration. He ordered a bottle of (S) 2-Butanol for his chiral starting material. He also remembered that the

S_{N} 2

goes best on primary halides so he made methyl halide and sodium (S) 2-butoxide after warming these reagents together he obtained an excellent yield of 2-Methoxy butane.

2-Methoxy butane

a n h y d r o u s H I - ------- \to

Products formed are:

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Preparation of Alcohols from Carbonyl Compounds

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