Nucleophilic substitution encompasses an exceptionally diverse array of reagents and functional groups. Nucleophilic substitution also occurs by multiple mechanisms and obeys a variety of rate laws.

This experiment asks you to measure the rates at which different organochlorides and organobromides undergo nucleophilic substitution using two different reagents. You will also compare your data with measurements obtained by other students and try to identify (and rationalize) structural factors that affect reactivity.

Time required: 1 laboratory session

Credit

This experiment was introduced to Reed students by Dr. James Rego in 2003, but it has a very long history (e.g. "Laboratory Experiments in Organic Chemistry" by Jerry R. Mohrig, 1968). Our version is based on the one that Jim brought from Swarthmore College.