Imagine a sample that is enriched in the R enantiomer. If the % ee of the sample is 83%,
(a) what percent of the mixture is racemic?
(b) What is the ratio of R to S?

Naproxen, a nonsteroidal anti-inflammatory drug that is the active ingredient in Aleve (p. 115), has a specific rotation of +66. One commercial preparation results in a mixture with a 97% enantiomeric excess.

a. Does naproxen have the R or the S configuration?

b. What percent of each enantiomer is obtained from the commercial preparation?

A solution of pure (S)-2-iodobutane ([α] = +15.90°) in acetone is allowed to react with radioactive iodide, ¹³¹I^–, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.

a. Determine the percentages of (R)- and (S)-2-iodobutane in the product mixture.

(S)-Propranolol, a drug used for the treatment of anxiety, has a specific rotation of -25.5° . Attempting to prepare it in enantiopure form, a chemist produced a compound that gave a specific rotation of -18.3° . What is the ratio of (S)- to (R)-propranolol produced by the chemist?

(R)-Selegiline, a monoamine oxidase (MAO) inactivator, was approved by the FDA in 1989 for the treatment of Parkinson's disease. In pure form, it has a specific rotation, [α]²⁰_D = - 11.0°. What is the expected specific rotation of a mixture containing 64% S and 36% R?

A chemist working on the synthesis of (+)-pilocarpine, an alkaloid used in the treatment of dry mouth and glaucoma, produced a mixture of enantiomers that gave a specific rotation [α]_D = +97°. Based on the specific rotation of the pure enantiomer, calculate the ratio of (+)- to (-)-pilocarpine produced by the chemist.

The α- and β-anomers of glucose are shown here.

In solution, these two epimers can interconvert through a process called mutarotation. What is the ratio of anomers (α:β) when the specific rotation is +52.6°

Under certain conditions, when (R)-2-bromobutane is heated with water, the S_N1 substitution proceeds twice as fast as the S_N2. Calculate the e.e. and the specific rotation expected for the product. The specific rotation of (R)-butan-2-ol is −13.5°. Assume that the S_N1 gives equal amounts of the two enantiomers.