Consider the reactions: (i) (ii) The mechanisms of reactions (i) and (ii) are, respectively:
and
and
and
and
The substrate in both reactions is isobutyl bromide, , which is a primary () alkyl halide. Primary alkyl halides undergo nucleophilic substitution predominantly via the mechanism because the corresponding primary carbocation required for an reaction is highly unstable . Furthermore, if an mechanism were to occur, the primary carbocation would undergo a hydride shift to form a more stable tertiary carbocation, leading to a rearranged product. Since the given product in both cases is the unrearranged ether (isobutyl ethyl ether), it confirms that no carbocation intermediate is formed. Therefore, both reactions proceed via the mechanism, irrespective of whether the attacking nucleophile is neutral () or a strong anionic nucleophile ().
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