An Updated Simple SN2 Reaction for the Undergraduate Organic Laboratory

SN2 reactions are of fundamental importance in introductory organic chemistry courses, and a number of experiments suitable for the first-semester undergraduate organic lab have been previously reported. Most of these experiments have used alkyl halides as electrophiles, but alkyl halides are often...

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Bibliographic Details
Published inJournal of chemical education Vol. 100; no. 1; pp. 376 - 379
Main Authors Khuong, Kelli S., Agnelli, Fabio, Parker, Matthew A.
Format Journal Article
LanguageEnglish
Published Easton American Chemical Society and Division of Chemical Education, Inc 10.01.2023
American Chemical Society
Subjects
Chemical reactions
Experiments
Halides
Organic chemistry
Sodium hydroxide
Toxicity
Synthesis
Laboratory Instruction
Second-Year Undergraduate
Reactions
Ethers
Thin Layer Chromatography
Alkylation
Organic Chemistry
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Summary:SN2 reactions are of fundamental importance in introductory organic chemistry courses, and a number of experiments suitable for the first-semester undergraduate organic lab have been previously reported. Most of these experiments have used alkyl halides as electrophiles, but alkyl halides are often less than ideal for reasons of toxicity/volatility and difficulty in TLC visualization. We report an updated methodology utilizing an alkyl tosylate, rather than a halide, as the electrophile. The SN2 reaction of 2-naphthol/sodium hydroxide with butyl p-toluenesulfonate is performed in a single 3 or 4 h lab period and affords a solid product in good yield. The tosylate electrophile gives students experience with a commonly encountered leaving group, is easily visualized on TLC, and has an improved safety profile.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.2c00794