O-Chem Alkyl Halide Reaction with a Chair Conformation

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The discussion revolves around a homework problem involving the reaction of an alkyl halide with sodium cyanide, specifically focusing on the expected product and the reaction mechanism. The participant suggests that the reaction is likely an SN2 due to the secondary carbon and the characteristics of cyanide as a nucleophile. However, they express uncertainty about how to depict the inversion of stereochemistry in the chair conformation and whether the bicyclic structure might hinder the approach of the nucleophile. The conclusion leans towards the possibility of no reaction occurring due to steric hindrance from the cyclic structure. Overall, the interaction highlights the complexities of stereochemistry and reaction mechanisms in organic chemistry.
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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!
 
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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?
 
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