Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 16: PROBLEM 16.23 (page 625)

Question: Draw the products of each Diels–Alder reaction, and indicate the stereochemistry.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Diels-Alder reaction

The Diels-Alder reaction occurs between a conjugated diene and an alkene called the dienophile.

The diene in a Diels-Alder reaction will be electron-rich, whereas the diene must be electron-poor alkenes and alkynes.

02

Example of Diels-Alder reaction

An example of Diels-Alder reaction is shown:

Example for Diels-Alder reaction

03

To find the product and stereochemistry

A cis dienophile will always form cis-substituted cyclohexene, and a trans dienophile will always form trans-substituted cyclohexene.

Representation of product of A

Here the dienophile is in cis position, combining with a diene to form a cis-substituted product.

Representation of product of B

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: The following reactions have been used to synthesize dieldrin and aldrin (named for Diels and Alder), two pesticides having a similar story to DDT (Section 7.4). Identify the lettered compounds in this reaction scheme.

Question: Draw a stepwise mechanism for the following reaction.

Question: Devise a synthesis of X from the given starting materials. You may use any organic or inorganic reagents. Account for the stereochemistry observed in X.

Question: Classify each diene as isolated or conjugated.

a.

b.

c.

d.

Question:Draw all reasonable resonance structures for acetic anhydride
See all solutions

Recommended explanations on Chemistry Textbooks

Making Measurements

Read Explanation

Kinetics

Read Explanation

Chemical Reactions

Read Explanation

Physical Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Nuclear Chemistry

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