Caprolactam, the monomer from which nylon 6 is synthesized, is prepared from cyclo- hexanone in two steps. In Step 1, cyclohexanone is treated with hydroxylamine to form cyclohexanone oxime. Treatment of the oxime with concentrated sulfuric acid in Step 2 gives caprolactam by a reaction called a Beckmann rearrangement. Propose a mecha- nism for the conversion of cyclohexanone oxime to caprolactam. HO NH NH,OH H,SO, Cyclohexanone Cyclohexanone Сaprolactam oxime

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
Caprolactam, the monomer from which nylon 6 is synthesized, is prepared from cyclo-
hexanone in two steps. In Step 1, cyclohexanone is treated with hydroxylamine to form
cyclohexanone oxime. Treatment of the oxime with concentrated sulfuric acid in Step 2
gives caprolactam by a reaction called a Beckmann rearrangement. Propose a mecha-
nism for the conversion of cyclohexanone oxime to caprolactam.
HO
NH
NH,OH
H,SO,
Cyclohexanone
Cyclohexanone
Сaprolactam
oxime
Transcribed Image Text:Caprolactam, the monomer from which nylon 6 is synthesized, is prepared from cyclo- hexanone in two steps. In Step 1, cyclohexanone is treated with hydroxylamine to form cyclohexanone oxime. Treatment of the oxime with concentrated sulfuric acid in Step 2 gives caprolactam by a reaction called a Beckmann rearrangement. Propose a mecha- nism for the conversion of cyclohexanone oxime to caprolactam. HO NH NH,OH H,SO, Cyclohexanone Cyclohexanone Сaprolactam oxime
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 3 images

Blurred answer
Similar questions
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