Lewis Acid-Base reaction vs Nucleophile attack.

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sakabato93

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208) The addition reaction of HBr with an alkene is...

A.) A one-step process
B.) an anti-Markovnikov reaction
C.) initiated by a nucleophilic attack
D.) a two-step process

The answer in the book is D, which makes sense: first step being protonation of the alkene and the second being a nucleophilic attack by the conjugate base.

I thought that you could argue C was true as well because the pi-bond could act as an nucleophile when attacking the proton.

So, I looked it up and I found out that when the pi electrons attack the electrophilic protion, its actually a lewis acid-base reaction, not a nucleophile attack. My question is... What's the difference?

Also, TPR OChem books states "nucleophiles are attracted--and donate a pair of electrons--to electrophiles. When the electrophile accepts the electron pair (a Lewis acid/base reaction), a new covalent bond forms between the two species."

Can anyone help a brother out?

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