Kelli S. Khuong, Fabio Agnelli, and Matthew A. Parker <br/><br/>
An Updated Simple SN2 Reaction for the Undergraduate Organic Laboratory  (Journal Article)  

 - Washington, United States  :American Chemical Society  ,January 10, 2023 
 - 376-379p. 
 - American Chemical Society, Volume 100, Issue 1 .
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<br/><br/> Abstract:-<br/><br/>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.<br/><br/> 
<br/><br/><label>ISSN: </label>0021-9584 
<br/><br/><label>Source: </label> RIEBPL Library 
<br/><br/><label>Subjects--Topical Terms: </label><br/>Second-Year Undergraduate<br/> Organic Chemistry <br/>Laboratory Instruction <br/>Alkylation Ethers Reactions <br/>Synthesis Thin Layer<br/> Chromatography
<br/><br/><label>Dewey Class. No.: </label>540.7