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Chapter 5: Q.16 (page 190)
What is the maximum number of stereoisomers possible for a compound with:
a. three stereogenic centers;
b. eight stereogenic centers?
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What is the maximum number of stereoisomers possible for each compound?
a.
b.
c.
Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers.
a.
b.
c.
a. Locate all the tetrahedral stereogenic centers in discodermolide, a tumor inhibitor isolated from the Caribbean marine sponge Discodermiadissoluta.
b. Certain carbon–carbon double bonds can also be stereogenic centers. With reference to the definition in Section 5.3, explain how this can occur, and then locate the three additional stereogenic centers in discodermolide.
c. Considering all stereogenic centers, what is the maximum number of stereoisomers possible for discodermolide?
An acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products. How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers.
State how each pair of compounds is related. Are they enantiomers, diastereomers, constitutional isomers, or identical?
a.
b.
c.
d.
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