Stereoisomeric Reaction Products

Reactions of three different enantiomers are shown below. In each reaction two stereoisomeric products are produced; one is an achiral meso compound and the other is a single enantiomer. Note that the use of tert-butylhydroperoxide as a co-reactant in the second and third reactions permits the use of catalytic amounts of osmium tetroxide.
Draw a structural formula for each of the designated products, using the wedge/hatched bond tool to show the configuration of stereogenic carbons. To draw a formula use the drawing window opened by the Draw Formulas button. Do not draw hydrogen atoms. When you are finished, Submit your formula and then check it by pressing the Check Molecule button. A help screen is available for the drawing window.

If you wish to practice drawing stereo formulas with this Editor Click Here.

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This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.
JME Molecular Editor v2002.05 by: by Peter Ertl