Chapter 5: Q.25 (page 196)
Which of the following cyclic molecules are meso compounds?

a.

b.

c.
Short Answer
- Not a meso
- Meso
- Not a meso
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Chapter 5: Q.25 (page 196)
Which of the following cyclic molecules are meso compounds?

a.

b.

c.
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Without drawing out the structures, label each pair of compounds as enantiomers or diastereomers.
a. (2R,3S)-hexane-2,3-diol and (2R,3R)-hexane-2,3-diol
b. (2R,3R)-hexane-2,3-diol and (2S,3S)-hexane-2,3-diol
c. (2R,3S,4R)-hexane-2,3,4-triol and (2S,3R,4R)-hexane-2,3,4-triol
For the given ee values, calculate the percentage of each enantiomer present.
a. 90% ee
b. 99% ee
c. 60% ee
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?
Artemisinin and mefloquine are widely used antimalarial drugs. A ball-and-stick model of artemisinin appears on the cover of this text.
Label the two stereogenic centers in each compound and draw all possible stereoisomers.

a.

b.
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