A student left some alkyl halides (RCl and RBr) in an open container for several minutes. What happened to the composition of the halide mixture during that time? Assume that some liquid remains in...

A student left some alkyl halides (RCl and RBr) in an open container for several minutes. What happened to the composition of the halide mixture during that time? Assume that some liquid remains in the container. 

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llltkl | College Teacher | (Level 3) Valedictorian

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When a mixture of alkyl halides (chloride and bromide) is left in open air, two possibilities arise:

1. Being highly volatile, the two halides would evaporate at a disproportionate rate making the liquid that is left over richer in the lesser volatile alkyl bromide.

2. The moisture in air initiates nucleophilic substitution reactions on alkyl halides resulting in the formation of corresponding alcohols as the immediate products. Once again, the alkyl chloride would react much faster making the unreacted halide that is left over richer in the bromide. The product alcohol, being liquid, would also remain in the liquid that would be left over there.

Therefore, composition of the liquid mixture produced when a student left some alkyl halides (RCl and RBr) in an open container for several minutes, assuming that some liquid remains in the container, has two distinct characteristics:

1. The alkyl bromide to alkyl chloride ratio rises considerably. Concentration of alkyl bromide remains almost unchanged, while that of alkyl chloride falling considerably.

And

2. It contains substantial amount of alcohol resulting from the hydrolysis of the alkyl chloride.

Sources:

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