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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

Question: Predict the products of the following reactions

a. Cyclopentanone +Br2 in acetic acid

The following compounds can be synthesized by aldol condensations, followed by further reactions. (In each case, work backward from the target molecule to an aldol product, and show what compounds are needed for the condensation.)

Some (but not all) of the following keto esters can be formed by Dieckmann condensations. Determine which ones are possible, and draw the starting diesters.

The following compounds can be synthesized by aldol condensations, followed by further reactions. (In each case, work backward from the target molecule to an aldol product, and show what compounds are needed for the condensation.)

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
See all solutions

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