Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
Book Icon
Chapter 11.8, Problem 13P

(a)

Interpretation Introduction

Interpretation:

To predict the product of acid-catalyzed hydrolysis of given ester.

Concept Introduction:

An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester.  The addition of acid promotes the protonation of oxygen atom in the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom.  The more withdrawal of electron density of oxygen atom decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile.  The acid catalyzed reaction mechanism is written as,

Essential Organic Chemistry (3rd Edition), Chapter 11.8, Problem 13P , additional homework tip  1

Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.

(b)

Interpretation Introduction

Interpretation:

To predict the product of acid-catalyzed hydrolysis of given ester.

Concept introduction:

An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester.  The addition of acid promotes the protonation of oxygen atom in the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom.  The more withdrawal of electron density of oxygen atom decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile.  The acid catalyzed reaction mechanism is written as,

Essential Organic Chemistry (3rd Edition), Chapter 11.8, Problem 13P , additional homework tip  2

Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.

(c)

Interpretation Introduction

Interpretation:

To predict the product of acid-catalyzed hydrolysis of given ester.

Concept Introduction:

An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester.  The addition of acid promotes the protonation of oxygen atom in the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom.  The more withdrawal of electron density of oxygen atom decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile.  The acid catalyzed reaction mechanism is written as,

Essential Organic Chemistry (3rd Edition), Chapter 11.8, Problem 13P , additional homework tip  3

Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.

Blurred answer
Students have asked these similar questions
Draw the organic product for the following acid-catalyzed hydrolysis reaction. H2SO4, H20
Draw the products of the following hydrolysis. Н CH2 "CHз О—Н Нзс Н
Which of these is the most viable route for the preparation or synthesis of a carboxylic acid? O Alpha-carbon substitution of ketones O Oxidation of aldehydes O Nucleophilic acyl substitution of amides O Elimination of alcohols O Nucleophilic addition of ketones

Chapter 11 Solutions

Essential Organic Chemistry (3rd Edition)

Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
Text book image
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning