Chapter 5: Q.38 (page 206)
Label each pair of compounds as constitutional isomers, stereoisomers, or not isomers of each other.
Short Answer
- Stereoisomers
- Constitutional isomers
- Not isomers of each other
Not isomers of each other
Chapter 5: Q.38 (page 206)
Label each pair of compounds as constitutional isomers, stereoisomers, or not isomers of each other.
Not isomers of each other
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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 (โ)-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 (โ)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.
e. How is each compound drawn in part (d) related to (โ)-ephedrine?
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A natural product was isolated in the laboratory, and its observed rotation was +10ยฐ when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of water. What is the specific rotation of this compound?
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