Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 9: Q58. (page 378)

Question: Draw a stepwise, detailed mechanism for the following intramolecular reaction that forms a cyclic ether.

Short Answer

Expert verified

Answer

Step by step solution

01

Step-by-Step SolutionStep 1: Formation of cyclic ethers

Cyclic ethers will be formed from intramolecular SN2 (bimolecular substitution) reactions that occur between two -OH groups

02

The mechanism of the given reaction

The conjugate acid of the -OHis the best leaving group. On reaction with an acid, the-OHbecomesO+H2, and it leaves the substrate molecule and forms a 3°tertiarycarbocation intermediate.

Then, the other -OHacts as a nucleophile, and it forms a bond with the 3°tertiarycarbocation, and thus, the product cyclic ether is formed.

Formation of cyclic ether

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: a) What is the major alkene formed when A is dehydrated with H2SO4 ? (b) What is the major alkene formed when A is treated with POCl3and pyridine? Explain why the major product is different in these reactions.

Question: Draw the product formed when is treated with each reagent.

a.SOCl2, Pyridine

b. TsCl, Pyridine

c. H2SO4

d. HBr

e. PBr3then NaCN

f. POCl3,Pyridine

Question: Draw the product of each reaction.

, a.

b.

c.

d.

Question: Explain why the treatment of anisole with HBr yields phenol and but not bromobenzene.

Question: Draw the product of each reaction:


a.

b.


c.


d.
See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Kinetics

Read Explanation

The Earths Atmosphere

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Nuclear Chemistry

Read Explanation

Inorganic 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.

Sign-up for free