Please rank the following aromatic compounds in order of their reactivity in ele

Question

Please rank the following aromatic compounds in order of their reactivity in electrophilic aromatic substitution: anisole, nitrobenzene, acetophenone, toluene, benzene. Briefly explain your answer.

Explanation / Answer

The order will be anisole>toluene>benzene>acetophenone>nit… An electrophilic aromatic substitution reaction requires the benzene ring to donate electrons to the electrophile. The rates of reaction parallel electron availability. Anisole, with the non-bonded electron on an oxygen atom, are able to donate electrons to the benzene ring and make it the most reactive (and ortho/para director). Because a methyl group is a weak electron donor, it too will be an o/p director and more reactive than benzene. A carbonyl carbon attached to a benzene ring is electron withdrawing, so this ring will be less reactive than benzene. It will now be a meta director as the meta position is the less depleted of electrons than the o/p positions by the carbonyl group. (Hint, draw the resonance structure for acetophenone (do anisole also)). Nitrobenzene is the least reactive because the nitrogen attached to the ring is even more electron withdrawing.

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