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Chapter 22: Q19P (page 1166)

Give the expected products for the aldol condensations of

  1. propanal.
  2. phenylacetaldehyde
  3. pentan-3-one.

Short Answer

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Step by step solution

01

Aldol condensation

Aldol Condensations are some of the most important enolate reactions of carbonyl compounds.

In this reaction, two or more molecules combine, often with the loss of a small molecule such as water or alcohol, forming the product known as aldol.

Aldol reaction takes place in two mediums:

  • Acidic medium
  • Basic medium
02

Aldol condensation of propanal

Propanal reacts with the hydroxide ion to form the enolate, which serves as a nucleophile. Then the enolate nucleophilic attack on another molecule of propanal. In the last step, Protonation gives the aldol product which is.

03

Aldol condensation of phenylacetaldehyde

Phenylacetaldehyde reacts with the hydroxide ion to form the enolate, which serves as a nucleophile. Then the enolate nucleophilic attack on another molecule of phenylacetaldehyde. In the last step, Protonation gives the aldol product, which is.

04

Aldol condensation of pentan-3-one

Pentan-3-one reacts with the hydroxide ion to form the enolate, which serves as a nucleophile. Then the enolate nucleophilic attack on another molecule of pentan-3-one. In the last step, Protonation gives the aldol product, which is.

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Most popular questions from this chapter

Question: Predict the products of the following reactions

e.

In Solved Problem 22-9, the target molecule was synthesized using a Michael addition to form the bond that is 尾,纬 to the upper carbonyl group. Another approach is to use a Michael addition to form the bond that is尾,纬to the other (lower) carbonyl group. Show how you would accomplish this alternative synthesis.

Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound

b.

Show how an acetoacetic ester synthesis might be used to form a 未 -diketone such as heptane-2,6-dione.

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.
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