April 25, 2024, 12:05:11 PM
Forum Rules: Read This Before Posting


Topic: mechanism  (Read 2869 times)

0 Members and 1 Guest are viewing this topic.

Offline Snake

  • Regular Member
  • ***
  • Posts: 17
  • Mole Snacks: +0/-1
mechanism
« on: October 15, 2006, 04:25:20 PM »
Hey guys.. i have this question which asks to show the mechanism with stereochemistry.. i don't know how to do it showing sterochemistry can anyone help pleasee..





Offline movies

  • Organic Minion
  • Retired Staff
  • Sr. Member
  • *
  • Posts: 1973
  • Mole Snacks: +222/-21
  • Gender: Male
  • Better living through chemistry!
Re: mechanism
« Reply #1 on: October 15, 2006, 09:01:05 PM »
In this reaction you will make predominantly one diastereomer of product in favor of the other.  The idea of the question is to draw a transition state which explains why the one diastereomer is preferred.

Here is a hint: the diastereomers would arise from attack at one of the two faces of the cabonyl carbon.  How do you think the presence of the t-butyl group will affect these transition states?  It might not be an obvious steric interaction, but something which is a consequence of the arrangement of the t-butyl group in space (axial or equatorial).  Think about how that affects other substituents around the ring as well.

Sponsored Links