Chapter 5: Q.31 (page 200)
For the given ee values, calculate the percentage of each enantiomer present.
a. 90% ee
b. 99% ee
c. 60% ee
Short Answer
- 95% A and 5% B.
- 99.5% A and 0.5% B.
- 80% A and 20% B.
Chapter 5: Q.31 (page 200)
For the given ee values, calculate the percentage of each enantiomer present.
a. 90% ee
b. 99% ee
c. 60% ee
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Get started for freeA molecule is achiral if it has a plane of symmetry in any conformation. Each of the following conformations does not have a plane of symmetry, but rotation around a carbon–carbon bond forms a conformation that does have a plane of symmetry. Draw this conformation for each molecule.
a.
b.
Label each pair of compounds as constitutional isomers, stereoisomers, or not isomers of each other.
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?
The [α] of pure quinine, an antimalarial drug, is –165.
a. Calculate the ee of a solution with the following [α] values: –50, –83, and –120.
b. For each ee, calculate the percent of each enantiomer present.
c. What is [α] for the enantiomer of quinine?
d. If a solution contains 80% quinine and 20% of its enantiomer, what is the ee of the solution?
e. What is [α] for the solution described in part (d)?
Classify each pair of compounds as constitutional isomers or stereoisomers.
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