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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

Draw the products of the following reactions:

a. 1,3-cyclohexanedione + LDA/THF, followed by allyl bromide

b. g-butyrolactone + LDA/THF, followed by methyl iodide

c. 2,7-octanedione + sodium hydroxide

d. diethyl 1,2-benzenedicarboxylate + sodium ethoxide: (1) slow addition of ethyl acetate; (2) HCl

Alkylation of the following compound with methyl iodide under two different conditions forms two different ketoesters (A and B). Each ketoester forms a cyclic diketone (C and D) when treated with methoxide ion in methanol.

a. Draw the structures of A and B, and indicate the conditions used in the alkylation reaction that cause that ketoester to be formed.

b. Draw the mechanism for the conversion of A to C.

What alkyl bromide(s) should be used in the malonic ester synthesis of each of the following carboxylic acids?

a. propanoic acid

b. 2-methylpropanoic acid

c. 3-phenylpropanoic acid

d. 4-methylpentanoic acid

What compound is formed when a dilute solution of cyclohexanone is shaken with NaOD inD2O for several hours?

Can 2,4-pentanedione undergo an intramolecular aldol addition? If so, why? If not, why not?
See all solutions

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