Chapter 5: Q.11 (page 187)
Which group in each pair is assigned the higher priority?
a.
b.
c.
d.
e. localid="1648296449951"
f.
Short Answer
a.
b.
c.
d.
e.
f.
Chapter 5: Q.11 (page 187)
Which group in each pair is assigned the higher priority?
a.
b.
c.
d.
e. localid="1648296449951"
f.
a.
b.
c.
d.
e.
f.
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Get started for freeThe 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?
How are the compounds in each pair related to each other? Are they identical, enantiomers, diastereomers, constitutional isomers, or not isomers of each other?
a.
and
b.
and
c.
and
d.
and
e.
and
f.
and
Locate the stereogenic centers in each molecule. Compounds may have one or more stereogenic centers.
b.
c.
d.
e.
f.
Label each stereogenic center as R or S.
a.
b.
c.
d.
e.
f.
g.
h.
The amino acid (S)-alanine has the physical characteristics listed under the structure.
a. What is the melting point of (R)-alanine?
b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?
c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?
d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?
e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.
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