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[awilly]

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[jwest88]

The simplest explanation is that O is more electronegative and is more stable with a negative charge than N. However, O isn't just leaving on its own. It actually complexes with the leftover AlH3 b/c the aluminum now has an empty p orbital again once it's given up one of its hydrides. Therefore, a complex of O-AlH3 leaves in the reduction of an amide.

 

[jwest88]

Ya, when you start talking about Cl, Br, and I then it's more about their size and how they can delocalize a negative charge better b/c they're bigger. In the case that you stated though, the main difference between O and N is that O is more electronegative. F is super electronegative but small, so it can't delocalize its negative charge as well as Cl, Br, or I.

 

[StarlingForce1]

The simplest explanation is that O is more electronegative and is more stable with a negative charge than N. However, O isn't just leaving on its own. It actually complexes with the leftover AlH3 b/c the aluminum now has an empty p orbital again once it's given up one of its hydrides. Therefore, a complex of O-AlH3 leaves in the reduction of an amide.

Jesus, it's thinking like that that gets 42 on MCAT lol. Feel like tutoring?