Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 17: 17-57P (page 847)

An aldol addition can be catalyzed by acids as well as by bases. Propose a mechanism for the acid-catalyzedaldol addition of propanal.

Short Answer

Expert verified

In an aldol addition reaction, the enolate ion of an aldehyde or a ketone reacts with the carbonyl carbon of another molecule of aldehyde or ketone, which results in the formation of a -hydroxy aldehyde or a -hydroxy ketone. The new C ¬ C bond forms between the -carbon of one molecule (the nucleophile) and the carbonyl carbon. Therefore, the carbon attached to OH is adjacent to the carbon attached to the carbonyl group.

Step by step solution

01

Aldol addition reaction

In an aldol addition reaction, the enolate ion of an aldehyde or a ketone reacts with the carbonyl carbon of another molecule of aldehyde or ketone, which results in the formation of a -hydroxy aldehyde or a -hydroxy ketone. The new C ¬ C bond forms between the -carbon of one molecule (the nucleophile) and the carbonyl carbon. Therefore, the carbon attached to OH is adjacent to the carbon attached to the carbonyl group.

02

Mechanism of the reaction

03

Kinetic enolate formation

When the temperature is low, LDA will remove the-H which is less substituted.

The reaction and the products are given below:

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Use retrosynthetic analysis to plan a synthesis of the following target molecules. The only carbon-containing compounds available for the syntheses are cyclohexanol, ethanol, and carbon dioxide.

(a)

(b)

(c)

(d)

How many stereoisomers are obtained from each of the synthesis described in Problem 14?

Describe how the following compound can be synthesized from compounds containing no more than six carbons.

Propose a mechanism for the following reaction.

How could each of the following compounds be prepared from cyclohexanone?

a.

b.

c.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Inorganic Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Making Measurements

Read Explanation

Kinetics

Read Explanation

Chemical Analysis

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free