(Journal Article) Kelli S. Khuong, Fabio Agnelli, and Matthew A. Parker creator text Washington, United States :American Chemical Society ,January 10, 2023 monographic eng

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376-379p. Abstract:- 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. ***______{For Hard Copy, Please visit Library.}________*** Second-Year Undergraduate Organic Chemistry Laboratory Instruction Alkylation Ethers Reactions Synthesis Thin Layer Chromatography 540.7 0021-9584 RIEBPL Library https://pubs.acs.org/doi/epdf/10.1021/acs.jchemed.2c00794 https://pubs.acs.org/doi/epdf/10.1021/acs.jchemed.2c00794 231030 20231106102824.0