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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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Drawn are four isomeric dimethylcyclopropanes.
a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and B; A and C; B and C; C and D?
b. Label each compound as chiral or achiral.
c. Which compounds, alone, would be optically active?
d. Which compounds have a plane of symmetry?
e. How do the boiling points of the compounds in each pair compare: A and B; B and C; C and D?
f. Which of the compounds are meso compounds?
g. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?
The [伪] of pure quinine, an antimalarial drug, is 鈥�165.
a. Calculate the ee of a solution with the following [伪] values: 鈥�50, 鈥�83, and 鈥�120.
b. For each ee, calculate the percent of each enantiomer present.
c. What is [伪] 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 [伪] for the solution described in part (d)?
Consider Newman projections (A鈥揇) for four-carbon carbohydrates. How is each pairof compounds related: (a) A and B; (b) A and C; (c) A and D; (d) C and D? Choose fromidentical molecules, enantiomers, or diastereomers.
Draw in a plane of symmetry for each molecule.
a.
b.
c.
d.
Label the two stereogenic centers in each compound and draw all possible stereoisomers.
a.
b.
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