Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 24: Q.52. (page 962)

Question: Draw a stepwise mechanism for the following variation of the aldol reaction, often called a nitro aldol reaction.

Short Answer

Expert verified

Answer

Mechanism

Step by step solution

01

Nitro Aldol Reaction

The Henry- reaction or the nitro-aldol reaction is the C-C bond formation reaction which occurs between a nitroalkane and a carbonyl group-containing compound in the presence of a mild base.

02

Mechanism of Nitro Aldol Reaction

The base attacks the acidic hydrogen of the nitroalkane to form a carbanionic center which undergoes resonance stabilization with the nitrogen atom.

As a result, a double bond is generated between the nitrogen and the carbon atom which attacks as a nucleophile on the electron-deficient carbonyl carbon of the carbonyl compound. The product contains an additional C-C between the two starting reactants.

03

Explanation

Stepwise mechanism of the given reaction

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

Question: What starting materials are needed to prepare each compound by the Michael reaction?

Question: Draw the products formed in each crossed aldol reaction.

a.

b.

Question: Identify compounds A and B, two synthetic intermediates in the 1979 synthesis of the plant growth hormone gibberellic acid by Corey and Smith. Gibberellic acid induces cell division and elongation, thus making plants tall and leaves large.

Question: Draw a stepwise mechanism for the following Robinson annulation. This reaction was a key step in a synthesis of the steroid cortisone by R. B. Woodward and co-workers at Harvard University in 1951.

Question: Following the two-step reaction sequence depicted in Figure 24.5, write out the steps needed to convert A to B.
See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Chemistry Branches

Read Explanation

Inorganic Chemistry

Read Explanation

Making Measurements

Read Explanation

Nuclear Chemistry

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