You need to consider what type of molecules are reactive in each one. For an Sn2 reaction, the primary halides are most reactive (except for methyl bromide). Both of these are primary halides and will be reactive. For Sn1 reactions, an intermediate carbocation must form before the nucleophile can react. The allyl cation and benzyl cation are both extremely stable due to multiple resonance forms for each one. Therefore, since they form stable cations, they will be reactive with Sn1 also.

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chemb

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12 years ago

First, bromide is a decent leaving group, much better than chloride, but not as good as iodide, of course. Sn1 reactions go through a carbocation. Thus, these both have good stabilized carbocations, either benzylic or allylic cation, which are both stabilitized by resonance. While for Sn2 reactions, these are PRIMARY centers so that they have minimized steric interactions in the Sn2 process.

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