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.
Esteb, John J.; Magers, John R.; McNulty, LuAnne M.; and Morgan, Paul, "A Flexible Solvolysis Experiment for the Undergraduate Organic Laboratory" / (2009): -.
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