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I'm having trouble understanding why the top SN2 reaction proceeds faster. I know that benzylic and allylic halides react faster in SN2 reactions than non-conjugated halides. I think it's because the transition state is more stable but how can you explain that using MO Theory?

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This is what my professor drew for this question but I don't understand it all. Any help would be appreciated :)

Why is the top SN2 reaction faster?

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