O-Chem Alkyl Halide Reaction with a Chair Conformation

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In summary, the conversation discusses a homework problem in which the expected product is being determined for a reaction between a compound and sodium cyanide. The problem involves considering the possibility of an SN2 reaction and the challenges of drawing a correct chair conformation. The conversation concludes with the realization that the other cyclic structure may hinder the reaction.
  • #1
persephone
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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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  • #2
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?
 
  • #3
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?
 

Related to O-Chem Alkyl Halide Reaction with a Chair Conformation

1. What is an alkyl halide?

An alkyl halide is a compound that contains a halogen atom (fluorine, chlorine, bromine, or iodine) bonded to a carbon atom in a molecule.

2. What is a chair conformation in organic chemistry?

A chair conformation is a three-dimensional shape that is commonly used to represent cyclohexane molecules. It is the most stable conformation for cyclohexane due to the minimal steric hindrance between the substituents on the carbon atoms.

3. How do alkyl halides react with a chair conformation?

Alkyl halides can undergo substitution reactions with a chair conformation. In this reaction, the halogen atom is replaced by a different functional group, such as an alkyl group or hydrogen atom.

4. What factors influence the reactivity of alkyl halides in chair conformation reactions?

The reactivity of alkyl halides in chair conformation reactions can be influenced by several factors, including the type of halogen atom, the type of alkyl group attached, and the steric hindrance around the carbon atom where the substitution occurs.

5. What are some common products of alkyl halide reactions with a chair conformation?

The products of alkyl halide reactions with a chair conformation can vary depending on the specific reaction conditions, but some common products include alkanes, alkenes, and substituted alkyl halides.

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