[lrw1793]

I can draw the cationic intermediates but I'm a bit unsure as to how to draw the resonance forms. For E would the positive charge be shared around the benzene ring? For D the lone pair of the nitrogen would stabilise the positive charge by conjugation, right? But does it not have resonance forms that also share the positive charge around the benzene ring?

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[lrw1793]

Sorry I should have said - the question is, with reference to the cationic intermediates explain why D, and not E is formed. Taking into account that it is very unfavourable to disrupt an aromatic ring

[kriggy]

If you draw the resonance form when nitrogen donates its electron pair into the system, then the second electron pair moves to the C3 carbon. I dont think the positive charge is shared around the benzene ring.

I hope I answered your qusetion