Quick Hydroboration question

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

BiomajorPreDent

Senior Member
10+ Year Member
Joined
Dec 18, 2008
Messages
653
Reaction score
3
Points
4,551
  1. Dental Student
When dealing with alkynes:

i know with excess borane you get a ketone but with 1 eqiv do you get only the enol? I am confused
 
Last edited:
Enols are tautomers of ketones (or aldehydes.)

I think it depends on what you remove the borane with. For example, when the borane complex attacks the alkyne, it can be removed with acetic acid to produce a cis alkene. If you remove the borane with H2O2, then you get anti-mark addition of a vinyl alcohol which tautomerizes to a ketone (aldehyde on terminal alkynes.)
 
Top Bottom