Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 18: Q69P (page 973)

Show a complete mechanism for this equilibrium established in diethyl ether with HCl gas as catalyst.

Short Answer

Expert verified

All steps involved in the mechanism for the synthesis of the given product is shown as below.

(a) Protonation of the nitrogen atom takes place at first.

(b) One of the lone pair on oxygen atom attacks the carbon of double bond, where the double bond gets rearranged.

(c) A chloride anion from attacks the hydrogen present on the hydroxy group which gives the desired product.

Step by step solution

01

Mechanism

All steps involved in the mechanism for the synthesis of the given product is shown as below.

(a) Protonation of the nitrogen atom takes place at first.

(b) One of the lone pair on oxygen atom attacks the carbon of double bond, where the double bond gets rearranged.

(c) A chloride anion from attacks the hydrogen present on the hydroxy group which gives the desired product.

02

Mechanistic pathway

The complete mechanism for the reaction

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

In the mechanism for acetal hydrolysis shown, the ring oxygen atom was protonated first, the ring was cleaved, and then the methoxy group was lost. The mechanism could also be written to show the methoxy oxygen protonating and cleaving first, followed by ring cleavage. Draw the alternative mechanism.

For each compound,

  1. Name the functional group,
  2. Show what compounds result from complete hydrolysis.

Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.

(a) bromobenzene → propiophenone

(b) CH3CH2CN → heptan-3-one

(c) benzoic acid → phenyl cyclopentyl ketone

(d) 1-bromo-hept-2-ene → oct-3- enal

Propose mechanisms for

(a) the acid-catalyzed hydration of chloral to form chloral hydrate.

(b) the base-catalyzed hydration of acetone to form acetone hydrate

Give the structures of the carbonyl compound and the amine used to form the following imines.

(a)

(b)

(c)

(d)

(e)

(f)
See all solutions

Recommended explanations on Chemistry Textbooks

Ionic and Molecular Compounds

Read Explanation

Physical Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

Read Explanation

Nuclear 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