Carbon oxygen bond stability?

[SublimeGD]

2 quick ochem questions...

1. Why is a carbon oxygen double bond more thermodynamically stable than a carbon oxygen single bond?

2. Can -OH be a leaving group in basic conditions, it would seem strange to protinate it in basic conditions?

Thanks!

 

[chemisttree]

2 quick ochem questions...

1. Why is a carbon oxygen double bond more thermodynamically stable than a carbon oxygen single bond?

2. Can -OH be a leaving group in basic conditions, it would seem strange to protinate it in basic conditions?

Thanks!

More thermodynamically stable than what? Than RRC⁺-O^-? Or R-CH₂-OH?

OH is never a good leaving group unless the negative charge is somehow dealt with. In what base catalyzed reaction do you see OH- as a leaving group?