What question did this study set out to answer?

This study aims to assess how competing electrophiles impact nucleophilic substitution reactions.

March 28, 2026

A Competitive Nucleophilic Substitution Experiment Analyzed by Thin Layer Chromatography

Key Points

This study aims to assess how competing electrophiles impact nucleophilic substitution reactions.
Performed a competitive substitution reaction using primary and secondary electrophiles
Used a single carboxylate nucleophile to form alkylated products
Applied thin layer chromatography for product analysis
Students identified the major substitution product to infer the reaction mechanism
Outcomes indicated whether the reaction occurred via SN1 or SN2 mechanisms
TLC effectively determined product distribution without the need for GC or NMR

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.

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