November 28, 2024, 04:44:07 AM
Forum Rules: Read This Before Posting


Topic: enol stability in asymmetric ketone  (Read 2146 times)

0 Members and 2 Guests are viewing this topic.

Offline insertwittyname

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +1/-1
enol stability in asymmetric ketone
« on: August 21, 2014, 02:38:36 PM »
If in a ketone, two different enol forms are possible, eg: O=C(C)CC can give both O/C(=C)CC and CC=C(C)O, which is major product in acidic medium?
I think the elimination of H should follow saytzeff rule, IE CC=C(C)O should be in the majority, as abstraction of that H by acid ought to be easier. Would I be correct?

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: enol stability in asymmetric ketone
« Reply #1 on: August 21, 2014, 03:14:03 PM »
That would be my guess as well. Under basic conditions, you could form kinetic product determined by greater acidity of methyl group. Under acid conditions, I would assume electron donation would prevail to give the more substituted enol as an E/Z mixture.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Re: enol stability in asymmetric ketone
« Reply #2 on: August 21, 2014, 07:08:42 PM »
Sterically hindered bases might give the kinetic product instead of the thermodynamic product, so watch that!
        -Zack
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline orthoformate

  • Full Member
  • ****
  • Posts: 133
  • Mole Snacks: +14/-4
Re: enol stability in asymmetric ketone
« Reply #3 on: August 21, 2014, 10:27:24 PM »
it would depend when you measured the concentrations in aq. acid correct?

Offline Vidya

  • Full Member
  • ****
  • Posts: 839
  • Mole Snacks: +46/-62
  • Gender: Female
  • Online Chemistry and Organic Chemistry tutor
    • Online Chemistry Tutor
Re: enol stability in asymmetric ketone
« Reply #4 on: August 22, 2014, 05:59:00 AM »
It will depend on the stability of the enolate ion formed during the mechanism.Electron donating groups will destabilize it and electron withdrawing groups will stabilize it.

Sponsored Links