/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q43P Explain why compound A will not ... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 28: Q43P (page 1239)

Explain why compound A will not undergo a ring-opening reaction under thermal conditions, but compound B will.

Short Answer

Expert verified

An eight-membered ring cannot accommodate a trans double bond in the ring.

A ten membered ring can accommodate a trans double bond in the ring.

Step by step solution

01

Ring-opening of Compound A

Under thermal conditions, the compound A forms an eight-membered ring, and the conjugated double bonds are cis to each- other as shown below:

The condition for the ring-opening reaction is the double bond should be trans to each other. However, the eight-membered ring cannot accommodate double in trans position due to its small size. Therefore, compound A does not go electrocyclic ring-opening reaction.

02

Ring-opening of Compound B

Compound B forms a ten-membered ring under the thermal condition of ring-opening, and also the position of double bond are trans to each other. Therefore, compound B undergoes an electrocyclic ring-opening.

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.

Over 30 million students worldwide already upgrade their learning with 91影视!

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

a. Propose a mechanism for the following reaction. (Hint:An electrocyclic reaction is followed by a Diels鈥揂lder reaction.)

b. What would be the product if trans-2-butene were used instead of ethene?

Draw the product of each of the following sigmatropic rearrangements:

a. Name the kind of sigmatropic rearrangement that occurs in each of the following reactions.

b. Using arrows, show the electron rearrangement that takes place in each reaction.

A student found that heating any one of the isomers shown here resulted in scrambling of the deuterium to all three positions on the five-membered ring. Propose a mechanism to account for this observation.

Why was a deuterated compound used in the last reaction on the preceding page?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

Read Explanation

Nuclear Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Organic 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.