Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 16: PROBLEM 16.26 (page 630)

Question: Draw the product (A) of the following Diels-Alder reaction. A was a key intermediate in the synthesis of the addicting pain reliever morphine, the chapter-opening molecule.

Short Answer

Expert verified

Answer

Step by step solution

01

Diels-Alder reaction

The Diels-Alder reaction is a syn addition concerning the diene and the dienophile.

The stereochemistry of the diene and dienophile are preserved during the reaction. The Diels-Alder reaction is stereospecific.

02

Mechanism of Diels-Alder reaction

The mechanism of the Diels-Alder reaction follows a concerted pathway because all the bond rupture and bond making occur simultaneously.

03

Find A

The Diels-Alder reaction required for the formation of the morphine can be represented in the following manner:

From this reaction, the compound A formed is shown below:

Structure of A

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: One step in the synthesis of dodecahedrane (Section 4.11) involved reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4 . This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.

Question: Rank the following compounds in order of increasing stability.

a.

b.

c.

Question: Devise a stepwise synthesis of each compound from dicyclopentadiene using a Diels–Alder reaction as one step. You may also use organic compounds having ≤ 4 C’s, and any required organic or inorganic reagents:

a.

b.

c.

Question: Explain why the cyclopentadienide anion A gives only one signal in its 13C NMR spectrum.

Question: One step in the synthesis of occidentalol, a natural product isolated from the eastern white cedar tree, involved the following reaction. Identify the structure of A and show how A is converted to B.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Read Explanation

Physical Chemistry

Read Explanation

Making Measurements

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Chemical Reactions

Read Explanation

The Earths Atmosphere

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