Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
3rd Edition
ISBN: 9780137533268
Author: Paula Bruice
Publisher: PEARSON+
Question
Book Icon
Chapter 11, Problem 46P
Interpretation Introduction

Interpretation:

Whether the acid-catalyzed hydrolysis of acetamide is a reversible or irreversible reaction has to be found and explained.

Concept introduction:

Acid catalyzed reaction: In acid hydrolysis of amide, acid protonates carbonyl oxygen of amide which increases the electrophilicity of the carbonyl carbon. Water acts as a nucleophile gets attached to the carbonyl carbon of amide to form tetrahedral intermediate(A) which on losing proton get converted to tetrahedral intermediate(B). The nitrogen of tetrahedral intermediate (B) gets protonated to form tetrahedral intermediate(C). The NH3 group is eliminated from the tetrahedral intermediate (C) and after that, it gets protonated to form NH4+. The mechanism of acid-catalyzed hydrolysis of amides is:

Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+), Chapter 11, Problem 46P

Blurred answer
Students have asked these similar questions
How much of each solution should be used to prepare 1L of a buffer solution with a pH of 9.45 using 3M Na2CO3 and 0.2M HCI? Given: Ka 1 = 4.3 × 10-7, Ka2 = 4.69 × 10-11
Add substituents to draw the conformer below (sighting down the indicated bond), then rotate the back carbon to provide the anti staggered conformer. + H3C H Ph H Problem 25 of 30 Drawing Atoms, Bonds and Rings Charges Tap a node to see suggestions H H H Undo Rasat Remove Done Finish update Rotate Submit
what temperature does a 50% (mole fraction) of ammonia/water liquid mixture boil at 1 atm

Chapter 11 Solutions

Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)

Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
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
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
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
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole