Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 22: Q77P-b (page 1206)

Propose mechanisms for the following reactions.

Short Answer

Expert verified

Mechanism followed as:

Step by step solution

01

Step-by-Step Solution Step 1: Claisen condensation

It is the nucleophilic acyl substitution reaction of ether forming the enolate ion with another ether group that leads to the form α,β unsaturated ketone.

02

Formation of the product

As the hydrogen is protonated from the reacting species which is ether formation of enolate ion occurs which combines with another group of ether followed by the removal of -OR formation of α,βunsaturated ketone occur.

03

Mechanism

The chemical reaction between carbonyl and methoxide takes place which leads to the generation of an anionic intermediate. After reaction with the given ester lead to the formation of the dicarbonyl compound.

The mechanism is as follows:

CLAISEN CONDENSATION

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

When cyclodecane-1,6-dione is treated with sodium carbonate, the product gives a UV spectrum similar to that of 1-acetyl-2-methylcyclopentene. Propose a structure for the product, and give a mechanism for its formation.

Write equations showing the expected products of the following enamine alkylation and acylation reactions. Then give the final products expected after hydrolysis of the iminium salts.

(a) pyrrolidine enamine of pentan-3-one + allyl chloride

(b) pyrrolidine enamine of acetophenone + butanoyl chloride

(c) piperidine enamine of cyclopentanone + methyl iodide

(d) piperidine enamine of cyclopentanone + methyl vinyl ketone

Phenylacetone can form two different enols.

  1. Show the structures of these enols.
  2. Predict which enol will be present in the larger concentration at equilibrium.

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 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.)
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Physical Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Chemical Reactions

Read Explanation

The Earths Atmosphere

Read Explanation

Kinetics

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