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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: marky02 on April 25, 2010, 04:57:53 PM

Title: alkene formation
Post by: marky02 on April 25, 2010, 04:57:53 PM

hi guys,have a difficult question

A chemist allows some pure (2S, 3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide (NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S, 3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C, give equations for their formation, and explain the stereospecificity of these reactions. Pay careful attention to stereochemistry.

Title: Re: alkene formation
Post by: MissPhosgene on April 25, 2010, 09:03:55 PM

What have you thought of so far?

Title: Re: alkene formation
Post by: Smrt guy on April 26, 2010, 11:22:31 PM

Think about the mechanism of the reaction.  What type of reaction is this?

Title: Re: alkene formation
Post by: AC Prabakar on May 02, 2010, 04:23:45 AM

It is elimination reaction and stereochemical aspects are very important points in this reaction.

I couldn't paste the reaction with product.I am trying that.Propably tomorrow i will post.But with respect to stereochemical part i need to prepare the mechanism.