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Chapter 17: Q61P (page 848)

Show how 4-methyl-3-hexanol can be synthesised from 3-pentanone.

Short Answer

Expert verified

The answer is,

Reaction

Step by step solution

01

Chemical reaction

The reaction of 3-pentanone with a strong base like LDA (Lithium diisopropylamine) gives the enolate ion, which reacts with alkylation using alkyl chloride to give the product 4-methyl-3-hexanol.

02

Explanation

The reaction for the synthesis of 3-pentanone from 4-methyl-3-hexanol is as given below.

Reaction

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Most popular questions from this chapter

An 伪,尾-unsaturated carbonyl compound can be prepared by a reaction known as a selenenylation鈥搊xidation reaction. A selenoxide is formed as an intermediate. Propose a mechanism for the reaction.

Use retrosynthetic analysis to plan a synthesis of the following target molecules. The only carbon-containing compounds available for the syntheses are cyclohexanol, ethanol, and carbon dioxide.

(a)

(b)

(c)

(d)

a. If the biosynthesis of palmitic acid were carried out with CD3COSR and nondeuterated malonyl thioester, how many deuterium atoms would be incorporated into palmitic acid?

b. If the biosynthesis of palmitic acid were carried out with -OOCCD3COSR and nondeuterated acetyl thioester, how many deuterium atoms would be incorporated into palmitic acid?

There are other condensation reactions similar to the aldol and claisen condensations:

a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkin condensation:

b. What compound is formed if water is added to the product of a Perkin condensation?

c. The Knoevenagel condensation is the condensation of an aldehyde or a ketone that has no alpha- hydrogens and a compound such as diethyl malonate that has an alpha-carbon flanked by two electron- withdrawing groups. Draw the product obtained from the following Knoevenagel condensation:

d. What product is obtained when the product of a Knoevenagel condensation is heated in an aqueous acidic solution?

Do a retrosynthetic analysis on each of the following compounds, ending with the given starting materials:

(a)

(b)
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