Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 30: Q29E (page 1033)

Propose a pericyclic mechanism to account for the following transformation.

Short Answer

Expert verified

The pericyclic mechanism for the following transformation can be proposed.

Step by step solution

01

Sigma tropic rearrangement

The reaction is [3,3] sigma tropic rearrangement. There is an involvement of 3 electron pairs in the reaction. Thus, it is under thermal conditions through the suprafacial pathway to produce an enol. The enol was then tautomerized to produce ketone.

02

Cyclic mechanism for the transformation

The cyclic mechanism can be drawn as,

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

Do the following electrocyclic reactions take place in a conrotatory or
disrotatory manner? Under what conditions, thermal or photochemical, would you carry out each reaction?

Karahanaenone, a terpenoid isolated from oil of hops, has been synthesized by the thermal reaction shown. Identify the kind of pericyclic reaction, and explain how karahanaenone is formed.

Vinyl-substituted cyclopropanes undergo thermal rearrangement to yield cyclopentenes. Propose a mechanism for the reaction, and identify the pericyclic process involved.

Coronafacic acid, a bacterial toxin, was synthesized using a key step that involves three sequential pericyclic reactions. Identify them, and propose a mechanism for the overall transformation. How would you complete the synthesis?[pk1]

[pk1]Size should be 12 not 11.


Look at Figure 30-1, and tell which molecular orbital is the HOMO and whichis the LUMO for both ground and excited states of ethylene and 1,3-butadiene.
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Kinetics

Read Explanation

Chemical Reactions

Read Explanation

Ionic and Molecular Compounds

Read Explanation

The Earths Atmosphere

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