Revisiting the Bleach Oxidation of 4-tert-Butylcyclohexanol

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 23 (2018) pp 23-27

Revisiting the Bleach Oxidation of 4-tert-Butylcyclohexanol

Brian J. Esselman and Nicholas J. Hill*

Department of Chemistry, University of Wisconsin–Madison, 1101 University Avenue, Madison, WI 53706 USA, hill@chem.wisc.edu
Received November 21, 2017. Accepted January 31, 2018.

Published: 15 February 2018

Abstract. Procedural and assessment updates to the classic bleach oxidation of 4-tert-butylcyclohexanol to 4-tert-butylcyclohexanone are described. Specific modifications include monitoring of the reaction by thin-layer chromatography (TLC), analysis of the crude product by IR, GC-MS and ¹³C-APT NMR data, and investigation of the active oxidant and structure of the product by computational chemistry. Each modification promotes deeper student learning of the practical and theoretical concepts of the exercise.

Key Words: Laboratories and Demonstrations; organic chemistry; oxidation; mechanisms; spectroscopy; computational chemistry

(*) Corresponding author. (E-mail: hill@chem.wisc.edu )

Article in PDF format (320 KB) HTML format

Supporting Materials:

The supporting materials include the student laboratory manual chapter and instructor notes, examples of student NMR, IR, and GC-MS spectroscopic data, examples of final exam questions. Solutions to all laboratory and exam questions are available upon request from the author. (1.97 MB)