/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} 17-57P An aldol addition can be catalyz... [FREE SOLUTION] | 91影视

91影视

Log out

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 卢 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 卢 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.

Over 30 million students worldwide already upgrade their learning with 91影视!

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

Show how the following compounds can be prepared from cyclohexanone:

What two carbonyl compounds are needed to synthesize each of the following compounds, using a Robinson annulation?

What aldehyde or ketone would be obtained when each of the following compounds is heated in a basic aqueous solution?

(a) 2-ethyl-3-hydroxyhexanal

(b) 4-hydroxy-4-methyl-2-pentanone

(c) 2,4-dicyclohexyl-3-hydroxybutanal

(d) 5-ethyl-5-hydroxy-4-methyl-3-heptanone

An 伪,尾-unsaturated carbonyl compound can be prepared by a reaction known as a selenenylation鈥搊xidation reaction. A selenoxide is formed as an intermediate. Propose a mechanism for the reaction.

What aldol addition product is formed from each of the following compounds?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Making Measurements

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

Read Explanation

Nuclear Chemistry

Read Explanation

Chemical Reactions

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.