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Chapter 16: Q74P (page 795)

List three different sets of reagents (each set consisting of a carbonyl compound and a Grignard reagent) that could be used to prepare each of the following tertiary alcohols

Short Answer

Expert verified

a)

b)

Step by step solution

01

Formation of alcohol

The reaction of aldehydes or ketones with a Grignard reagent followed by the hydrolysis forms alcohol. The nucleophile attacks the carbonyl group and forms an intermediate. Protonation of the alkoxide ion gives the alcohol product.

02

Formation of the desired compound

a)

Treatment of 1-phenylpentan-1-one with ethyl magnesium bromide followed by the addition of dilute acid gives the required alcohol.

Formation of the desired product

b)

Treatment of hexan-3-one with ethyl magnesium bromide followed by the addition of dilute acid gives the required alcohol.

Formation of the desired product

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Most popular questions from this chapter

Which of the following compounds does not form an alcohol when it reacts with excess Grignard reagent?

A.

B.

C.

The compounds commonly known as “amino acids” are actually -aminocarboxylic acids (Section 21.0). What carbonyl compounds should be used to synthesize the two amino acids shown here?

Question: Name the following:

a.

b.

c.

d.

Propose a mechanism for each of the following reactions:

Draw the structure for each of the following:

a.

b.

c.

d.
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