Resumen de An Updated Simple SN2 Reaction for the Undergraduate Organic Laboratory
Kelli S. Khuong, Fabio Agnelli, Matthew A. Parker
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.
