December 23, 2024, 08:07:29 AM
Forum Rules: Read This Before Posting


Topic: iodoform reaction with a diketone  (Read 2557 times)

0 Members and 1 Guest are viewing this topic.

Offline insertwittyname

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +1/-1
iodoform reaction with a diketone
« on: December 21, 2015, 02:19:50 AM »
One of the step in an iodoform reaction is the abstraction of a proton from the CH3 group.
However, in a 1,3 diketone, the proton present in between the 2 carbonyl groups (eg. the proton on the third carbon in pent-2,4-dione aka acetylacetone) would be more acidic, and hence more readily abstracted. How does a diketone then give the iodoform reaction?

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: iodoform reaction with a diketone
« Reply #1 on: December 21, 2015, 04:15:20 PM »
You are on the right track. Let's follow the mechanism and see where it leads. Remember, even though enolization occurs that leads to halogenation, hydroxide also adds to the carbonyl group. What can happen?
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Sponsored Links