/*! 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} Q13P a. Draw the product of the follo... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 28: Q13P (page 1228)

a. Draw the product of the following reaction:


b. If the terminal sp2 carbon of the substituent attached to the benzene ring is labeled with 14C, where will the label be in the product?

Short Answer

Expert verified

The given reactant is the allyl vinyl ether; it will undergo Claisen rearrangement, a [3,3] sigmatropic rearrangement (involving three pairs of electrons),and forming a six-membered ring transition state. The reactions, therefore, must be able to take place by asuprafacial pathway.

Because [3,3] sigmatropic rearrangements involve three pairs of electrons, they occur by a suprafacial pathway under thermal conditions. The product is formed by breaking the sigma bond between the oxygen and carbon and joining the two fragments at the 3rd carbon form a keto form, which tautomerize to form the more stable enol form as the product is shown as follows:

Step by step solution

01

 Step 1: Product of Given reaction

The given reactant is the allyl vinyl ether; it will undergo Claisen rearrangement, a [3,3] sigmatropic rearrangement (involving three pairs of electrons),and forming a six-membered ring transition state. The reactions, therefore, must be able to take place by asuprafacial pathway.

Because [3,3] sigmatropic rearrangements involve three pairs of electrons, they occur by a suprafacial pathway under thermal conditions. The product is formed by breaking the sigma bond between the oxygen and carbon and joining the two fragments at the 3rd carbon form a keto form, which tautomerize to form the more stable enol form as the product is shown as follows:

02

Labeled Product

The given reaction is [3,3] sigmatropic rearrangement; the terminal carbon of the substituent attached to the benzene ring is labeled with 14C, which is the 3rd carbon from the one fragment formed by the breaking of the carbon-oxygen sigma bond.

The product is formed by joining the 3rd carbon of both the fragment formed by breaking a carbon-oxygen sigma bond and the labeled carbon that appears in the product is shown as follows:

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

Explain why two different products are formed from disrotatory ring closure of (2E,4Z,6Z)-octatriene, but only one product is formed from disrotatory ring closure of (2E,4Z,6E)-octatriene.

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.

Problem:Which of the following are correct? Correct any false statements.

a. A conjugated diene with an even number of double bonds undergoes conrotatory ring closure under thermal conditions.

b. A conjugated diene with an antisymmetric HOMO undergoes conrotatory ring closure under thermal conditions.

c. A conjugated diene with an odd number of double bonds has a symmetric HOMO.

Draw the product formed when each of the following compounds undergoes an electrocyclic reaction
a. under thermal conditions.
b. under photochemical conditions.

Will a concerted reaction take place between 1,3-butadiene and 2-cyclohexenone in the presence of ultraviolet light?
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Chemical Reactions

Read Explanation

Nuclear Chemistry

Read Explanation

Ionic and Molecular Compounds

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.