Chad's video question

[ioweisi]

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Hello, I was just watching Chad's orgo video about nucleophiles and electrophiles and he said carbon is a better nucleophiles than nitrogen which is better than oxygen which is better than fluorine (C>N>O>F). So why are carbon, nitrogen, and oxygen considered better nucleophiles than fluorine? Isn't fluorine more electro negative (it has more electrons making it more "electron rich")?

Thank You!

 

[ScarletKnight24]

Hello, I was just watching Chad's orgo video about nucleophiles and electrophiles and he said carbon is a better nucleophiles than nitrogen which is better than oxygen which is better than fluorine (C>N>O>F). So why are carbon, nitrogen, and oxygen considered better nucleophiles than fluorine? Isn't fluorine more electro negative (it has more electrons making it more "electron rich")?

Thank You!

I am not sure if I am understanding your question but a good indicator whether something is a good nucleophile or not is the presence of negative charge.

Br-, Cl-, I-, and a few carbon nucleophiles like acetilyde are good nucleophiles. However Br-, Cl-, and I- are weak bases because they are conjugate bases of a strong acid.(Stronger acid, weaker conjugate base) and therefore have no basic property. They are very stable on their own and that is also why they are good leaving groups.

alkoxide are both strong nucleophile and base.