O-Chem Alkyl Halide Reaction with a Chair Conformation

  • Thread starter Thread starter persephone
  • Start date Start date
  • Tags Tags
    Reaction
Join the discussion
Registration is free. Start your own thread to ask a follow-up.
Sign up Log in
2 replies · 5K views
persephone
Messages
12
Reaction score
0

Homework Statement


I am working on a homework problem for my Organic Chemistry class. In one particular question, our teacher asks for the expected product when http://img301.imageshack.us/img301/5986/homeworkproblem1qu8.th.jpg reacts with sodium cyanide.

Homework Equations


N/A


The Attempt at a Solution


I have a feeling it would be an SN2 reaction because the leaving group is attached to a secondary carbon and cyanide is a weak base but a good nucleophile. However, an SN2 reaction requires an inversion of the stereocenter, and I am not sure how to draw that with this particular chair conformation. Would I just substitute CN for the methylsulfonate group and put it in equitorial position?
Thanks in advance!
 
Last edited by a moderator:
Physics news on Phys.org

Discussion

Remember that an SN2 reaction requires that the reactant approach the reaction center from behind. Is that likely in this bicyclic compound? Is anything in the way?
 
chemisttree said:
Remember that an SN2 reaction requires that the reactant approach the reaction center from behind. Is that likely in this bicyclic compound? Is anything in the way?

Well that other cyclic structure could be in the way...so I'm guessing the answer is no reaction?