1A. The product from your reaction has a sharp melting point, indication that it

Question

1A. The product from your reaction has a sharp melting point, indication that it is either meso-hydrobenzoin or a racemic mixture of the (1R, 2R) and (1S, 2S) enantiomers. Why is it not possible that your product is either the (1R, 2R) or the (1S, 2S) pure enantiomer?

1B. What is the enantiomeric excess (ee) of a racemic mixture of enantiomers?

1C. If the racemic mixture of the hydrobenzoins were formed in the reaction of benzil with sodium borohydride, describe a set of experimental conditions for which you might get a non-racemic mixture of these two products. You can chance anything except the two starting materials.

(The reaction being described in the first part of the questions is the reation of benzil with sodium borohydride. It's Experiment 13 in Understanding the Principles of Organic Chemistry: A Laboratory Course, which is online in PDF form for free)

If you could explain your answers, I would really appreciate it. Thanks!

Explanation / Answer

a) Both have approximately same melting point.

b) Enantiomeric excess (ee) is a measurement of purity used of chiral molecules. A racemic mixture has an ee of 0%/

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