Determining Aromaticity When to use carbocation/anion

[BabyBombers24]

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Hey SDN peers, I have 2 questions on aromatics that I'm fuzzy on

When we're determining the aromaticity. Should we only apply carbocation when asking for SN1/E1 type questions that require a stable intermediate? (i.e. which compound reacts fastest in SN1 or dehydrates quickest E1) and just examine carbanion when asking for the most stable aromatic/acid?

and

for non carbon atoms like nitrogen and oxygen do we only count the lone pair that inside the ring and not outside?

thank you!

 

[ZOZO_SAGA]

Here's a video that answers your second questions to which lone pairs to include when determining aromaticity. Skip all the way to 27:30. Hope this helps.

 

[BabyBombers24]

thank you you're the man! best of luck on your upcoming exam