April 24, 2024, 07:42:24 PM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Grignard reaction on ester - stereochemistry  (Read 7414 times)

0 Members and 1 Guest are viewing this topic.

Offline 2moles

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
Grignard reaction on ester - stereochemistry
« on: May 26, 2009, 05:47:21 AM »
Hi!

I have a question here... I have an ester reacting with 2 moles of CH3MgBr. I know my product is a tertiar alcohol, but how is the stereochemistry? Is it possible to know whether it is the R or S configuration? Or doesn't this matter since the two methylgroups are the same?

A bit confused..

Thanks if you answer :)
Logged

Offline Arctic-Nation

  • Chemist
  • Full Member
  • *
  • Posts: 265
  • Mole Snacks: +33/-9
Re: Grignard reaction on ester - stereochemistry
« Reply #1 on: May 26, 2009, 08:46:03 AM »
It does indeed not matter. You can only have a stereocenter with four different substituents, so with your two methyl groups you'll never get enantiomers.
Logged

Offline Loyal

  • Regular Member
  • ***
  • Posts: 84
  • Mole Snacks: +7/-5
  • Gender: Male
Re: Grignard reaction on ester - stereochemistry
« Reply #2 on: May 26, 2009, 09:40:54 PM »
Remember that the Grignard reagent attacks the Ester once which removes the O-R group from the carbon and thus it leaves a Ketone which can react with a second mole of the Grignard.  This means your R-MgCl attaches twice.
Logged
Chemistry Student(Senior) at WSU
Pages: [1]   Go Up
« previous next »
Sponsored Links