Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 27: Q 44. (page 1102)

Question: What type of sigmatropic rearrangement is illustrated in each reaction?

Short Answer

Expert verified

Answer

a. 1,5sigmatropic shift

b.2,3sigmatropic shift

Step by step solution

01

Sigmatropic shift

  • A sigmatropic rearrangement is an intramolecular pericyclic reaction.
  • The reactant’s σ bond is broken, and theπbonds rearrange to form a new bond in the product.
  • In a sigmatropic rearrangement, the number of π bonds is constant in the reactant and product
02

 [1,5] and [2,3] sigmatropic shifts

The 1,5sigmatropic shift is associated with the rearrangement of the group at the first and fifth positions.

The 2,3sigmatropic shift is associated with the rearrangement of the group at the second and third positions.

03

Explanation

a. In the given conversion, the groups at the first position rearrange themselves at the fifth position. Therefore, it is a 1,5sigmatropic shift.

b. In the given conversion, the groups at the second position rearrange themselves at the third position. Therefore, it is a 2,3 sigmatropic shift.

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: Consider the following electrocyclic ring closure. Does the product form by a conrotatory or disrotatory process? Would this reaction occur under photochemical or thermal conditions?

Question: Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

Question: Draw the products of each reaction.

Question: What compound forms geranial (Figure 21.6) by a Cope rearrangement ?

Question: Draw a stepwise, detailed mechanism for the following reaction.
See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Inorganic Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Chemistry Branches

Read Explanation

Chemical Analysis

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