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The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 28
(2023) pp 115-119
A Competitive Nucleophilic Substitution Experiment Analyzed by Thin Layer Chromatography
Courtney J. Hastings
Department of Chemistry and Biochemistry, Loyola University Maryland, 4501 N. Charles Street, Baltimore, Maryland, 21210, USA, cjhastings@loyola.edu
Received June 27, 2023. Accepted August 14, 2023.
Published: 14 October 2023
Abstract. A discovery-based experiment for the first semester organic chemistry laboratory is described, involving competing electrophiles in an aliphatic substitution reaction. In the experiment, a primary and secondary electrophile compete for a single carboxylate nucleophile, forming the two alkylated products in unequal amounts. Students identify the major product of the competition reaction to determine whether the substitution proceeds through the SN1 or SN2 reaction mechanism. The outcome of the competition reaction is determined solely by TLC analysis, making it well-suited for institutions where it is impractical to analyze student samples by GC or NMR
Key Words: Laboratories and Demonstrations; organic chemistry;
(*) Corresponding author.
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Article in PDF formatt(159 KB) HTML format
Supporting Materials:
Includes a list of chemicals and supplies (including CAS numbers), notes for the instructor, lab handout with student instructions and post-lab questions, online pre-lab questions, HPLC chromatograms of substitution experiments. (2670 KB)
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