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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

Using cyclopentanone as the reactant, show the product of a. acid-catalyzedketo鈥揺nolinterconversion. b. an aldol addition. c. an aldol condensation.

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?

Propose a mechanism for the formation of fructose-1, 6-bisphosphate from dihydroxyacetone phosphate and glyceraldehyde-3-phosphate, using hydroxide ion as the catalyst.

When a dilute solution of acetaldehyde in D2O containing NaOD is shaken, explain why the methyl hydrogens are exchanged with deuterium but the hydrogen attached to the carbonyl carbon is not.

What reagents should be used to prepare the following compounds?
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