Logout Open In App
Open In App
Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Chapter 26: Q 37. (page 1072)

Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.

Short Answer

Expert verified

Answer

Mechanism

Step by step solution

01

Sulfur Ylide Reaction

The sulfur ylide reacts with the enone compound to form a resonance-stabilized enolate containing a good leaving group. This reaction is called Corey Chaykovsky Cyclopropanation.

02

Intramolecular elimination reaction

The nucleophilic center thus formed in the enolate attacks the electrophilic carbon attached to the leaving group, and a cyclopropane ring is formed in the compound.

03

Mechanism of the given reaction

The mechanism of the given reaction is shown below.

Mechanism

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

One step in the synthesis of the nonsteroidal anti-inflammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?

Many variations of ring-closing metathesis have now been reported. Tandem ring-opening– ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon– carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.

a.

b.

Draw the product formed from the ring-closing metathesis of each compound. Then, devise a synthesis of each metathesis starting material from benzene, alcohols with less than five carbons, and any needed organic and inorganic reagents.

a.

b.

In addition to using CHX3and base to synthesize dihalocarbenes (Section 26.4), dichlorocarbene (CCL2)can be prepared by heating sodium trichloroacetate. Draw a stepwise mechanism for this reaction.

What product is formed in the Suzuki coupling of A and B? This reaction was a key step in the synthesis of losartan, a drug used to treat hypertension.
See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

The Earths Atmosphere

Read Explanation

Nuclear Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Chemistry Branches

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