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Chapter 17: Q24P (page 820)

How could you prepare the following compound using a starting material that contains no more than three carbons?

Short Answer

Expert verified

A reaction followed as:

Step by step solution

01

LDA reagent

Lithium di-isopropyl amide is the most basic reagent is used to abstract the proton from the molecule. It is used in the aldol condensation to form the enolate ion from the enol or ketone by abstracting the proton for further reaction.

02

Formation of the compound

The given compound is formed by the acetone followed by the formation of the enolate ion than in reaction with the alkyl halide the alkyl group attaches to the enolate oxygen and the removal of the halide ion occurs and forms the desired product.

03

Mechanism

Mechanism followed as:

  1. Acetone reacts with LDA

  2. Enolate ion formed

  3. Enolate reacts with ethyl bromide

  4. Ethyl attack on enolate oxygen

  5. Removal of bromide on desired product formed

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Most popular questions from this chapter

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

How can you synthesize the following compounds from starting materials containing no more than four carbons?

(a)

(b)

(c)

(d)

Show how the following compounds can be synthesized from the given starting materials:

(a)

(b)

A carboxylic acid is formed when an α-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for the following Favorskii reaction.

What reagents should be used to prepare the following compounds?
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