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Terpenes, chirality problem set Soln_1

Terpenes, chirality problem set Soln_1 - Tartaric acid is...

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CHEM 312 Terpenes, Chirality Problem Set Solutions 1. Highlight the isoprene units in the following molecules. Star the chiral carbons and determine (a) the total number of possible stereoisomers; and (b) the number of spots that would be seen on a TLC plate. * * * * * * * * * lavandulol: 1 c.s.; 2 stereoisomers; 1 spot on TLC grandisol: 2 c.s.; 4 stereoisomers; 2 spots on TLC dendrolasin: 0 c.s.; 1 stereoisomer; 1 spot on TLC cineole: 0 c.s.; 1 stereoisomer; 1 spot on TLC b-vetivone: 2 c.s.; 4 stereoisomers; 2 spots on TLC indomyrmecin: 4 c.s.; 8 stereoisomers; 4 spots on TLC
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2. Glucose is one stereoisomer of the “aldohexose” class of sugars. Glucose has four chiral carbons. What is the how many stereoisomers of glucose are there? 2 4 =16 possible stereoisomers
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3.
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Unformatted text preview: Tartaric acid is shown below. Draw all the possible stereoisomers of tartaric acid. Notice that one set of enantiomers are actually identical molecules (the enantiomer of one compound is actually itself). What do you think that means for the optical rotation of that stereoisomer? HO OH O O OH OH HO OH O O OH OH HO OH O O OH OH HO OH O O OH OH enantiomers drawn as enantiomers, but same compound Since the enantiomer of the molecule is itself, the rotation of this isomer is 0û 4. If D-tartaric acid has an optical rotation of +12˚, what is the optical rotation of: a. L-tartaric acid? =12˚ b. a 50:50 mixture of D- and L-tartaric acid? = 0˚ c. a 75:25 mixture of D- and L-tartaric acid? = (0.75)(+12) + (0.25)(-12) = 6˚...
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