1. The problem statement, all variables and given/known data 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 [Broken] reacts with sodium cyanide. 2. Relevant equations N/A 3. 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!