EK says
" A carbonyl compound with a double bond between the α and ß carbon has some special properties. The carbocation that is produced at the carbonyl carbnon when the electrons shift to the oxygen atom (giving the oxygen a negative charge) is stabilized by resonance. Additionally, the electron withdrawing carbonyl group pulls electrons from the carbon-carbon double bond and makes the ß-carbon less suspectible to attack by a nucleopholic (electrophilic addition). Thus, rather than the nucleophile adding to the ß-carbon, if may sometime add to the oxygen atom, forming the enol-keto tautomers."
They didn't put a diagram of this process in the book, so I'm just wondering....How does the nucleophile add to an oxygen atom? Doesn't make sense to me.
Please explain. Thank you.
" A carbonyl compound with a double bond between the α and ß carbon has some special properties. The carbocation that is produced at the carbonyl carbnon when the electrons shift to the oxygen atom (giving the oxygen a negative charge) is stabilized by resonance. Additionally, the electron withdrawing carbonyl group pulls electrons from the carbon-carbon double bond and makes the ß-carbon less suspectible to attack by a nucleopholic (electrophilic addition). Thus, rather than the nucleophile adding to the ß-carbon, if may sometime add to the oxygen atom, forming the enol-keto tautomers."
They didn't put a diagram of this process in the book, so I'm just wondering....How does the nucleophile add to an oxygen atom? Doesn't make sense to me.
Please explain. Thank you.
