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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

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.

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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