Chemical Forums
1 Hour
1 Day
1 Week
1 Month
Forever
November 24, 2024, 01:48:29 AM
Forum Rules
: Read This Before Posting
Home
Help
Search
Login
Register
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
5,5-diphenylhydantoin
« previous
next »
Print
Pages: [
1
]
Go Down
Topic: 5,5-diphenylhydantoin (Read 9035 times)
0 Members and 1 Guest are viewing this topic.
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),
Logged
OC pro
Chemist
Full Member
Posts: 396
Mole Snacks: +36/-15
Gender:
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.
Logged
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.
Logged
orgopete
Chemist
Sr. Member
Posts: 2636
Mole Snacks: +213/-71
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=NCONH
2
from one of the C=O groups. Do the rearrangement to give the urea-acid. Loss of water should give the hydantoin.
Logged
Author of a multi-tiered example based workbook for learning
organic chemistry mechanisms
.
Print
Pages: [
1
]
Go Up
« previous
next »
Sponsored Links
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
5,5-diphenylhydantoin