I'm don't know the english terminology for chemistry so sorry for probably butchering some terms.

My question is, which of these is more reactive in an E1 reaction:

E1 reaction

The bottom two are the intermediates.

To determine the most reactive molecule, we look at the most stable intermediate. When trying to stabilize the positive charge, the benzyl has 3 resonances and the allyl has only 1. But in the resonance forms of the benzyl, it loses its aromaticity.

Which effect is more important, not losing aromaticity during resonance forms, or having more resonance forms?

Thanks for your help!

Note: A similar question was asked here: Is benzyl chloride or allyl chloride more reactive?, but my question is only specific to this E1 reaction, while the other question is a general reactivity question (and has no answer...).


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