Physical Sciences and Mathematics Commons^™

A Simple Sn2 Reaction For The Undergraduate Organic Laboratory, John Esteb

John Esteb

A simple procedure for the synthesis of n-butyl naphthyl ether is presented. This procedure represents an easy method for the production of an aryl ether by an SN2 reaction, uses ethanol as an environmentally friendly solvent, and does not require the use of a lachrymator. Product isolation is done by pouring the reaction mixture over ice and collecting the solid by suction filtration. Students typically recover from 7–95% of the ether.

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A Flexible Solvolysis Experiment For The Undergraduate Organic Laboratory, John Esteb, John Magers, Luanne Mcnulty, Paul Morgan, Kathryn Tindell, Anne Wilson

John Esteb

A simple SN1 reaction is presented that uses bromotriphenylmethane and a range of oxygen-based nucleophiles including water and various alcohols. This procedure represents a process that affords easy isolation of solid products. Typical student yields ranged from 17–128% with the average yield of 50%. Students obtained products with a melting point range of 140 to 164 °C. This procedure offers multiple ways to adapt this experiment from a straight solvolysis reaction to a discovery-based experiment that explores the effect of nucleophile (for a more advanced group) or the method of product isolation. Note: Link is to the article in a …