To give the explanation whether the acid-catalyzed hydrolysis of acetamide is a reversible or irreversible reaction. Concept introduction: 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 NH 3 group is eliminated from the tetrahedral intermediate (C) and after that, it gets protonated to form NH 4 + . The mechanism of acid-catalyzed hydrolysis of amides is:

Question

Want to see the full answer?

Answer 1

Question

Chapter 15, Problem 86P

Interpretation Introduction

Interpretation:

To give the explanation whether the acid-catalyzed hydrolysis of acetamide is a reversible or irreversible reaction.

Concept introduction:

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:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

achieve.macmillanlearning.com Canvas EA eac h Hulu YouTube G 3 methyl cyclobutanol - Google Search Ranking Phenol Acidity Course -236 - Organic Chemistry - Mac... ← Assessment Completed 10 of 22 Questions 1 + Netflix paramount plus chem hw Galdehyde reaction with grignard reagent... b My Questions | bartleby M Inbox - chenteislegit@gmail.com - Gmail Due: Fri, Jan 31 Resources Solution Penalized ? Hint Submit Answer Use retrosynthetic analysis to suggest two paths to synthesize 2-methyl-3-hexanol using the Grignard reaction. (Click and drag the appropriate image to the correct position in the reactions.) Route 1 Aldehyde 1 or +98 Aldehyde 2 Route 2 Q6 +100 Solved in 1 attempt Q7 +95 Solved in 2 attempts Q8 +98 Unlimited attempts possible + + Grignard 1 OH H3O+ Grignard 2 Answer Bank Q9 +90 MgBr Unlimited attempts possible CH3CH2CH2MgBr Q10 Unlimited attempts Q11 ? ? +100 in 1 attempt 2-methyl-3-hexanol CH3CH2MgBr H H о H Attempt 3

2) (4 pt) After the reaction was completed, the student collected the following data. Crude product data is the data collected after the reaction is finished, but before the product is purified. "Pure" product data is the data collected after attempted purification using recrystallization. Student B's data: Crude product data "Pure" product data after recrystallization Crude mass: 0.93 g grey solid Crude mp: 96-106 °C Crude % yield: Pure mass: 0.39 g white solid Pure mp: 111-113 °C Pure % yield: a) Calculate the crude and pure percent yields for the student's reaction. b) Summarize what is indicated by the crude and pure melting points.

Don't used hand raiting