November 24, 2024, 01:48:29 AM
Forum Rules: Read This Before Posting


Topic: 5,5-diphenylhydantoin  (Read 9035 times)

0 Members and 1 Guest are viewing this topic.

Offline Moz29386

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +0/-0
5,5-diphenylhydantoin
« on: May 04, 2010, 01:27:40 PM »
We are synthesisng 5,5-diphenylhydantoin from urea and benzil.

I need to know the mechanism for that synthesis if possible please.

I've searched the forum and this is what I found 

http://en.wikipedia.org/wiki/Benzilic_acid_rearrangement

But it doesnt help as the reaction is not complete.

Thanks.

Also; Describe a convienient method (with equations) for the synthesis of benzil. (do not include full experimental details),

Offline OC pro

  • Chemist
  • Full Member
  • *
  • Posts: 396
  • Mole Snacks: +36/-15
  • Gender: Male
Re: 5,5-diphenylhydantoin
« Reply #1 on: May 04, 2010, 03:11:02 PM »
It´s a simple condensation. 2 Moles of water will be formed. Thats all for the mechanism.

Offline Doc Oc

  • Chemist
  • Full Member
  • *
  • Posts: 564
  • Mole Snacks: +48/-12
Re: 5,5-diphenylhydantoin
« Reply #2 on: May 04, 2010, 03:29:25 PM »
It's not just a simple condensation, at least one of those ketones from the benzil has to be preserved in the final product.

Take a look at this paper:  J. Chem. Educ.  1986, 63, 650.

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: 5,5-diphenylhydantoin
« Reply #3 on: May 05, 2010, 01:09:42 PM »
I would try writing the mechanism as an aza-benzylic acid rearrangement. First form a C=NCONH2 from one of the C=O groups. Do the rearrangement to give the urea-acid. Loss of water should give the hydantoin.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Sponsored Links