The acid-catalyzed hydrolysis of an ester converts an ester into a carboxylic acid. Although there are two O atoms that can be protonated, the first step in the mechanism is believed to be protonation of the oxygen in the C=0 group. Based on charge stability, why is it favorable to protonate that oxygen? Hint: Draw out the products of each protonation. + Hо HO, НО Carboxylic acid Ester Alcohol

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
The acid-catalyzed hydrolysis of an ester converts an
ester into a carboxylic acid. Although there are two O
atoms that can be protonated, the first step in the
mechanism is believed to be protonation of the oxygen
in the C=0 group. Based on charge stability, why is it
favorable to protonate that oxygen? Hint: Draw out the
products of each protonation.
+ Hо
HO,
НО
Carboxylic
acid
Ester
Alcohol
Transcribed Image Text:The acid-catalyzed hydrolysis of an ester converts an ester into a carboxylic acid. Although there are two O atoms that can be protonated, the first step in the mechanism is believed to be protonation of the oxygen in the C=0 group. Based on charge stability, why is it favorable to protonate that oxygen? Hint: Draw out the products of each protonation. + Hо HO, НО Carboxylic acid Ester Alcohol
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY