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Chapter 17: Q14P (page 814)

How could each of the following compounds be prepared from a ketone and an organohalide?

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Step-by-Step SolutionStep 1: Alkylating the α-carbon

The process of alkylation is carried out by removing protons present on the α-carbon using a strong base (LDA). An enolate ion is formed, and then the addition of alkyl halide to the enolate ion occurs.

02

Preparation of compound (a) from symmetrical ketone and organohalide

a) The starting materials needed to prepare the given compound are 2-propanone (ketone) and 3-iodoprop-1-ene (organohalide). A strong base LDA is used to form an enolate ion, and then alkyl halide is added. The alkyl group of organohalide is put on the α-carbon of the ketone compound.


Preparation of compound (a)

03

Preparation of compound (b) from symmetrical ketone and organohalide

(b)The starting materials for preparing the given compound are 3-pentanone (ketone) and benzyl bromide (organohalide). A strong base LDA/THF is used to form an enolate ion, and then alkyl halide is added. The alkyl group of benzyl bromide is put on the α-carbon of the 3-pentanone.


Preparation of compound (b)

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Most popular questions from this chapter

Explain why alkylation of anα α -carbon works best if the alkyl halide used in the reaction is a primary alkyl halide, and why alkylation does not work at all if a tertiary alkyl halide is used.

What is the product of each of the following reactions?

Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water.

A β,γ-unsaturated carbonyl compound rearranges to a more stable conjugated α,β-unsaturated compound in the presence of either acid or base.

a. Propose a mechanism for the base- catalyzed rearrangement.

b. Propose a mechanism for the acid- catalyzed rearrangement.

β,γ-unsaturated carbonyl compound α,β-unsaturated carbonyl compound

What aldol addition product is formed from each of the following compounds?
See all solutions

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