Chromatography using a chiral stationary phase is able to separate a pair of enantiomers because one of the enantiomers forms a more tightly bound complex with the stationary phase. Assuming that the (S) enantiomer elutes more slowly, rationalize this result on a reaction coordinate diagram.

Questions (a)–(d) all refer to the following reaction, which has been engineered to produce one enantiomer to the exclusion of the other.

(c) Suppose the difference in activation energy is 1.6 kcal/mol. At what temperature would you produce C in 99% ee?

How might you separate enantiomers of 2-phenylpropionic acid?

A chemist prepared a racemic mixture of the enantiomeric sulfonic acids shown here. Suggest two ways that these might be separated.

When 0.200 g of lactose is dissolved in 10.0 ml of water and placed in a sample cell 10.0 cm in length, the observed rotation is +2°. Calculate the specific rotation of lactose.

Figure 6.52 <IMAGE> shows the lipase-catalyzed kinetic resolution of secondary alcohols. Show a reaction coordinate diagram that rationalizes the results obtained.

Calculate the observed rotation of a chiral mixture that contains 65% (S)-stereoisomer where the [α] of pure (S)-stereoisomer = -118.

An optically pure (R)-stereoisomer of a molecule has a specific rotation of – 20°. What specific rotation would be observed for a mixture of the (R) and (S) stereoisomer where there is an enantiomeric excess equal to (S) 60%.