April 26, 2024, 08:17:53 PM
Forum Rules: Read This Before Posting


Topic: Claisen condensation  (Read 5226 times)

0 Members and 1 Guest are viewing this topic.

Offline derster

  • New Member
  • **
  • Posts: 6
  • Mole Snacks: +0/-0
Claisen condensation
« on: May 05, 2007, 09:56:58 PM »
What product is formed in the mixed Claisen condensation between methyl benzoate and cyclohexanone?

Offline Yggdrasil

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 3215
  • Mole Snacks: +485/-21
  • Gender: Male
  • Physical Biochemist
Re: Claisen condensation
« Reply #1 on: May 05, 2007, 11:13:30 PM »
Please read the Forum Rules[/url].  You must show your attempt at answering the question before we will help you.

But, here is a questions to get you started:  Where are the acidic protons on your two reagents?

Offline Dolphinsiu

  • Full Member
  • ****
  • Posts: 349
  • Mole Snacks: +3/-7
  • Gender: Male
Re: Claisen condensation
« Reply #2 on: May 06, 2007, 03:37:44 AM »
      O                            O
       ll                             ll
Ph - C - O - Me +             C            --> ?
                             CH2       CH2
                              l            l
                             CH2       CH2
                                   CH2

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

From mechanism, base will attach alpha H in ketone.
Then the double bond is moved alpha C and carbonyl carbon while O become negative.

Then carbonyl carbon in ester is being attacked by alpha carbon --(nucleophilic addition)

Then OMe is a leaving group while enolate anion in ester move back to original to carbonyl carbon--(elimination)

Then only two product are formed.

MeOH + ?

(Please guess the another product!)





« Last Edit: May 06, 2007, 03:44:28 AM by Dolphinsiu »

Offline derster

  • New Member
  • **
  • Posts: 6
  • Mole Snacks: +0/-0
Re: Claisen condensation
« Reply #3 on: May 06, 2007, 12:04:09 PM »
ok thanks, i didn't realize we had to show our work on here first, i'm new to this forum and i'm not sure exactly how to put the structures in.  anyway i really appreciate your help dolphinsiu, i was able to get the other product after you explained that.  i really appreciate everyones help.  thank you

Sponsored Links