×
Log in to StudySoup
Get Full Access to Chemistry - Textbook Survival Guide
Join StudySoup for FREE
Get Full Access to Chemistry - Textbook Survival Guide

Amides such as acetamide ( ) are much weaker bases than

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 48SP Chapter 1

Organic Chemistry | 8th Edition

  • Textbook Solutions
  • 2901 Step-by-step solutions solved by professors and subject experts
  • Get 24/7 help from StudySoup virtual teaching assistants
Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

4 5 1 400 Reviews
15
4
Problem 48SP

Amides such as acetamide ( ) are much weaker bases than amines, such as ethylamine (CH3CH2NH2).

(a) Use resonance forms to show why the nonbonding electrons on the nitrogen atom of the amide are very

weakly basic.

(b) Strong acid is required to protonate the amide. Predict where acetamide will undergo protonation, and use resonance forms to show why the site you have chosen is more basic. (Hint: To compare basicities, compare the stabilities of the conjugate acids.)

Step-by-Step Solution:
Step 1 of 3

Solution 48SP

(a)

The structures of acetamide and ethyl amine are as follows:

 

The resonance structure of acetamide is as follows:

Here, the electron pair on N atom is not readily available to an acid for the protonation because the lone pairs involve in resonance stabilization.

Whereas, in ethyl amine there is no possibility for the resonance stabilization, so the lone pair of electrons on nitrogen atom are readily available for the protonation.

Therefore, the lone pair of electrons...

Step 2 of 3

Chapter 1, Problem 48SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: acetamide, use, such, Amide, show. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 48SP from 1 chapter was answered, more than 404 students have viewed the full step-by-step answer. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 48SP from chapter: 1 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. The answer to “Amides such as acetamide ( ) are much weaker bases than amines, such as ethylamine (CH3CH2NH2).(a) Use resonance forms to show why the nonbonding electrons on the nitrogen atom of the amide are veryweakly basic.(b) Strong acid is required to protonate the amide. Predict where acetamide will undergo protonation, and use resonance forms to show why the site you have chosen is more basic. (Hint: To compare basicities, compare the stabilities of the conjugate acids.)” is broken down into a number of easy to follow steps, and 75 words.

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

Amides such as acetamide ( ) are much weaker bases than

×
Log in to StudySoup
Get Full Access to Chemistry - Textbook Survival Guide
Join StudySoup for FREE
Get Full Access to Chemistry - Textbook Survival Guide
×
Reset your password