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Chapter 5: Q.30 (page 200)

What is the ee for each of the following mixtures of enantiomers A and B?

a. 95% A and 5% B

b. 85% A and 15% B

Short Answer

Expert verified

a. The ee is 90%.

b. The ee is 70%.

Step by step solution

01

Enantiomeric excess (ee)

The enantiomeric excess determines the excess amount of any one of the enantiomers (either R or S). It is also termed an optically pure compound.

02

Formula to calculate the ee

The formula to calculate the ee is as follows:

ee=%ofoneenantiomer-%ofotherenantiomer.

03

Explanation

a. The ee is calculated from the A and B as:

ee=95%-5%=5%

Therefore, the ee for enantiomers is 90%.

b. The ee is calculated from the A and B as:

ee=85%-15%=70%

Therefore, the ee for enantiomers is 70%.

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Most popular questions from this chapter

The shrub ma huang (Section 5.4 A) contains two biologically active stereoisomers-ephedrine and pseudoephedrine-with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once popular combination drug used by body builders to increase energy and alertness, while pseudoephedrine is a nasal decongestant.

a. Draw the structure of naturally occurring (–)-ephedrine, which has the 1R,2Sconfiguration.

b. Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2Sconfiguration.

c. How are ephedrine and pseudoephedrine related?

d. Draw all other stereoisomers of (–)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.

e. How is each compound drawn in part (d) related to (–)-ephedrine?

Draw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.

ethambutol

Draw a meso compound for each of the following molecules.

a.

b.

c.

A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.

HC≡C-C≡C-CH=C=CH-CH=CH-CH=CH-CH2CO2H

Locate the stereogenic centers in each compound.

a.

b.
See all solutions

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