Organic Lab Reactions 190

Organic Lab Reactions 190 - the creation of an additional...

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STEREQCHEMICAL CONFIGURATION 185 of selectivity which have been found in these compounds cannot always be extended to simpler molecules. However, differences in the ease of reduction of various types of carbonyl groups undoubtedly exist, depend- CH; CH2CH3 CHO XIV CH 2 CH 8 CH 8 ing not only upon the speed of reduction but also upon the reduction potential. The oxidation-reduction series •• 10 for various ketone-alcohol systems may give a clue to the direction in which progress may be made. Stereochemical Configuration of the Reduction Products In the reduction of an optically active ketone, the reaction results in
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Unformatted text preview: the creation of an additional asymmetric center, and two diastereoiso-mers are possible. In many cases it has been found that both isomers are formed, often in comparable amounts. For example, reduction of camphor (XV) gives a mixture of borneol and isoborneol (XVI). 6 Numerous other examples may be noted in the tables at the end of this chapter. However, the reduction of benzil (XVII) or benzoin (XVIII) is reported to give 90% of weso-hydrobenzoin (XIX). 5 . CH-C-W OH O xvin-CH—CH-OH OH XIX...
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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