GC/MS Analysis of the Competitive Alkylation of 2- Methylcyclohexanone: A New Experiment for Undergraduate Students

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 3 Issue 3(1998), S1430-4171(98)03210-5

GC/MS Analysis of the Competitive Alkylation of 2- Methylcyclohexanone: A New Experiment for Undergraduate Students

Anne B. Padias* and James A. Baron

Department of Chemistry, The University of Arizona, Tucson, Arizona 85721

Published online: 1 June 1998

Abstract. In this organic chemistry laboratory experiment, students perform two different alkylations of a-methylcyclohexanone. Conditions have been established that allow the students to achieve efficient anion formation using lithium diisopropylamide in tetrahydrofuran. First, the enolate is alkylated with either allyl bromide or benzyl bromide and the product analyzed by GC/MS. Subsequently, a competitive alkylation is performed using both electrophiles and the reaction mixture analyzed by GC/MS.

Key Words: Laboratories and Demonstrations; GS/MS; alkylation; undergraduate experiment; organic chemistry; gas chromatography; enolate; mass spectrometry

(*) Corresponding author. (E-mail: anne@u.arizona.edu)

Article in PDF format (49 KB )

Supporting Materials:

Student Handout. Gas Chromatography/ Mass Spectrometry, questions are provided here (116 KB) 10.1007/s0089798210b