a careless organic chemistry student was performing "competing nucleophiles in nucleophilic substitution reactions" experiment , and left his container of tert-butyl chloride and tert-butyl bromide open to the air for several hours. what happened to the composition of the halide mixture during this time

When tert-butyl chloride and tert-butyl bromide are left open to the air, they can undergo a reaction called nucleophilic substitution. Nucleophilic substitution reactions involve the replacement of a halogen atom (in this case, chlorine or bromine) by a nucleophile.

In this scenario, the reaction can occur through the reaction of the halide with water in the air. The water molecules can act as nucleophiles and substitute the halogen atom, resulting in the formation of alcohols.

The nucleophilic substitution reaction of tert-butyl chloride and tert-butyl bromide with water can be represented as follows:

tert-butyl chloride + water → tert-butyl alcohol + hydrochloric acid
tert-butyl bromide + water → tert-butyl alcohol + hydrobromic acid

As a result, the composition of the halide mixture will change over time, with the formation of the corresponding tert-butyl alcohols and the release of hydrochloric acid or hydrobromic acid, depending on the specific compound used.

It is important to note that the rate of this reaction is relatively slow, so several hours of exposure to air may not cause significant changes in the composition of the halide mixture.