Ketals

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.
Why can't ketals be formed from base catalysis?

I'd imagine it has to do with the mechanism. something needs to protonate the carbonyl oxygen so it can get kicked out by the ethylene glycol. then you need to make the resulting oh group a good enough leaving group to get kicked out by the other end of your reactant. the first part of my answer may not be exactly right but i think the second part is.
 
I reread some passages and I guess both ketals and acetals are unable to form under base conditions (it stops at the hemiketal and hemiacetal) which would make sense because OH cannot be protonated with base catalysis and it is not a good leaving group.
 

Similar threads

  • Question Question
Replies
3
Views
737