April 19, 2024, 04:26:48 PM
Forum Rules: Read This Before Posting


Topic: Hydroxy Acid with RLi  (Read 1971 times)

0 Members and 1 Guest are viewing this topic.

Offline vivekrai

  • Regular Member
  • ***
  • Posts: 71
  • Mole Snacks: +1/-5
  • Gender: Male
  • Love is in air
Hydroxy Acid with RLi
« on: February 27, 2012, 02:05:50 AM »
I'm unable to proceed very much. Since Et- is highly basic it abstracts the -COOH proton(See p1p.png). So that's all? Doesn't seem so because the problem says that the product is obtained in 65% yield.
" हर विफल्तापर पर न तुम आँसू बहाओ हर सफलता का यही पहला चरण है | "
**********************************************

Offline Fluorine

  • Chemist
  • Full Member
  • *
  • Posts: 202
  • Mole Snacks: +22/-5
  • Gender: Male
Re: Hydroxy Acid with RLi
« Reply #1 on: February 27, 2012, 03:47:42 AM »
You have three equivalents of ethyllithium, two could deprotanate (acid and alcohol) leaving the third to go for a nucleophilic attack on the carbonyl. That's how I see it proceeding.
I'm still learning - always check my work/answer.

"curse Pierre Jules César Janssen!"

Sponsored Links