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Chapter 22: Q23P (page 1169)

When propionaldehyde is warmed with sodium hydroxide, one of the products is 2-methylpent-2-enal. Propose a mechanism for this reaction.

Short Answer

Expert verified

Base-catalyzed aldol condensation reactionfollows thenucleophilic addition reaction.

In this reaction,enolate is formed, which acts as the strong nucleophile, thus getting attached carbon (electrophile)of the carbonyl group.

Step by step solution

01

Base-catalyzed Aldol condensation

Base-catalyzed aldol condensation reactionfollows thenucleophilic addition reaction.

In this reaction,enolate is formed, which acts as the strong nucleophile, thus getting attached carbon (electrophile)of the carbonyl group.

02

Mechanism for propionaldehyde when reacted with sodium hydroxide

When reacted with sodium hydroxide, propionaldehyde follows the base-catalyzed aldol condensation mechanism in which sodium hydroxide (base) removes a proton to form an enolate ion. The formed enolate ion adds to the carbonyl group of another propionaldehyde molecule. In the last step, Protonation of the alkoxide gives the aldol product 2-methylpent-2-enal.

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Most popular questions from this chapter

Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.

Show the products of the reactions of these carboxylic acids with PBr3/Br2before and after hydrolysis.

  1. pentanoic acid
  2. phenylacetic acid
  3. succinic acid
  4. oxalic acid

Predict the major products of the following reactions.

a)

Show how you would use the Robinson annulation to synthesize the following compounds.

The following compound results from base-catalyzed aldol cyclization of a 2-substituted cyclohexanone.

  1. Show the diketone that would cyclize to give this product.
  2. Propose a mechanism for the cyclization
See all solutions

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