To confirm the identity of the alkyl halide synthesized in this reaction, the product was subjected to two qualitative tests which distinguish between primary, secondary and tertiary halides. In the first, the product reacts with alcoholic silver nitrate to produce an insoluble salt whose color reflects the halide ion it contains. In the second, alkyl chlorides or bromides form an insoluble salt when they react with sodium iodide in acetone.
a. Write a mechanism for the reaction of an alkyl halide with alcoholic silver nitrate which depicts the type of substitution which occurs. Explain how this mechanism accounts for the relative rate of reactivity of primary, secondary and tertiary halides in this reaction