My prof asked us the requisites for e delocalization.

Sigma e delocalization
-Must have c-h bond next to a sp2C
Pi e delocalization
-Must have sp3 lone pair attach to an sp2C. Prof said there are more requisites besides on what ive written. I think if it has high en? What is hyperconjugative releases btw? And how can i know if its hyperconjugative? Sorry if i ask a lot. I just really one to know more. Thank you in adv for answering all of my questions...

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And also how would i know if the molecules or element in structure is either electrifilicity or nucleofilicity? For ex. Acetone. The carboxyl C is + and O is - but when you draw a canonical structure of it the H in ch3 became + and has double bond with carboxyl C. Why pls explain this to me...please
Pls answer