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Ch_322a_5.011 - Meso Compounds A Special Stereochemical...

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Meso Compounds: A Special Stereochemical Situation The maximum number of stereoisomers when there are two stereocenters is 2 2 = 4. But structural symmetry influences this analysis. Example: 2,3-dibromobutane There are two stereocenters in this compound. CH 3 -CH-CH-CH 3 Br Br * * The four possible stereoisomers of 2,3-dibromobutane are: C C C C CH 3 CH 3 CH 3 CH 3 Br Br Br Br H H H H C C CH 3 CH 3 Br Br H H C C CH 3 CH 3 Br Br H H 2S ,3R 2R, 3S 2S , 3S 2R,3R I II III IV At first view, it may appear that this compound exists in four unique stereoisomeric forms as found in 2,3-dibromopentane, but ..............
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symmetry reduces the number of stereoisomers from four to three. Structural Symmetry: The Meso Diastereomer C C C C CH 3 CH 3 CH 3 CH 3 Br Br Br Br H H H H C C CH 3 CH 3 Br Br H H C C CH 3 CH 3 Br Br H H 2S ,3R 2R, 3S 2S , 3S 2R,3R I II III IV A more careful inspection of the four possible stereoisomers reveals that I and II are not different because one structure may be superimposed on the other. They are the
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