HT3-2004 - Hour Examination #3, Chemistry 301-301A,...

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"One had to cram all this stuff into one's mind for the examinations,whether one liked it or not. This coercion had such a deterring effect on me that, after I had passed the final examination, I found the consideration of any scientific problems distasteful to me for an entire year." -Albert Einstein thanks to Seenu Susarla 20 points each question 1. In principle, cycloalkene 1 can give four products (two pairs of diastereomers) when treated with Br 2 in CH 3 OH. NOTE CAREFULLY: each diastereomer has a mirror image - its enantiomer. This question does not deal with these enantiomers, and you may ignore them. (a) What are the four possible products? We are not dealing with mechanism (yet). (b) The product mixture has zero optical rotation. Why? A single short sentence will suffice to answer this part. (c) One of the four possible products in (a) is by far the major compound formed. Use a detailed, careful mechanistic analysis of this reaction to explain which one it is and why it is the major product. H
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This note was uploaded on 03/07/2010 for the course ORGO 1 AND V.0243 taught by Professor Jones during the Spring '10 term at NYU.

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HT3-2004 - Hour Examination #3, Chemistry 301-301A,...

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