Assignment 2_Stereochemistry
1. There are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas
for these isomers. (b) Which of the isomers are chiral?
2. (a) Identify all of the chirality centers in
cortisone.
(b) Assign the appropriate (R) or (S)
designation for the configuration of each
chirality center in cortisone
3. (a) Identify all of the chirality centers in
cortisol.
(b) Assign the appropriate (R) or (S)
designation for the configuration of each
chirality center in cortisol
4. Write appropriate structural formulas for (a) molecules with the formula C6H12 that
contain one ring and that are enantiomers of each other, (b) molecules with the
formula C6H12 that contain one ring and that are diastereomers of each other.
5. Write appropriate structural formulas for (a) molecules with the formula C6H12 that
contain no ring and that are enantiomers of each other, and (b) molecules with the
formula C6H12 that contain no ring and that are diastereomers of each other.
6. There are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas
for these isomers. (b) Which of the isomers are chiral?
7. a) An aqueous solution containing 10 g of optically pure fructose was diluted to 500
mL with water and placed in a polarimeter tube 20 cm long. The measured rotation
was –5.20°. Calculate the specific rotation of fructose.
(b) If this solution were mixed with 500 mL of a solution containing 5 g of racemic
fructose, what would be the specific rotation of the resulting fructose mixture? What
would be its optical purity?
8. Write the organic products of each of the following reactions. If two stereoisomers are
formed, show both. Label all chirality centers R or S as appropriate.
(a) 1-Butene and hydrogen iodide
(b) (E)-2-Pentene and bromine in carbon tetrachloride
(c) (Z)-2-Pentene and bromine in carbon tetrachloride
9. The enzymatic hydration of aconitic acid yields two
products: citric acid and isocitric acid. Isocitric acid is
optically active; citric acid is not. What are the
respective constitutions of citric acid and isocitric
acid?
10. The antiparkinson drug droxidopa has the structural
formula shown with configurations at C-2 and C-3 of
S and R, respectively. Add appropriate wedges and/or
dashes (3D structure) to show the stereochemistry.
11. A certain natural product having [α]D + 40.3° was isolated. Two very different
structures were independently proposed for this compound. Which one do you think
is more likely to be correct? Why?
12. Sphingosine is a component of membrane lipids,
including those found in nerve and muscle cells. How
many stereoisomers are possible?
13. Draw the two chair conformations of cis-1-chloro-2-methylcyclohexane. Which is more
stable?
14. Draw the two chair conformations of trans-1-chloro-2-methylcyclohexane. Which is
more stable?
15. Identify each pair of relationships among the -OH
groups in glucose (red–blue, red–green, red–black,
blue–green, blue–black, green–black) as cis or trans.
16. Draw all possible stereoisomers of 1,2-cyclobutanedicarboxylic acid, and indicate the
interrelationships. Which, if any, are optically active?
Do the same for 1,3-cyclobutanedicarboxylic acid.
17. Draw tetrahedral representations of the following molecules: (a) The 2S,3R
enantiomer of 2,3-dibromopentane (b) The meso form of 3,5-heptanediol
18. (S)-1-Chloro-2-methylbutane undergoes light-induced reaction with Cl 2 to yield a
mixture of products, among which are 1,4-dichloro- 2-methylbutane and 1,2-dichloro-
2-methylbutane.
(a) Write the reaction, showing the correct stereochemistry of the reactant
and of the two products.
(b) One of the two products is optically active, but the other is optically inactive.
Which is which?
19. Compound A, C7H14, is optically active. On catalytic reduction over a palladium
catalyst, 1 equivalent of H2 is absorbed, yielding compound B, C7H16. On cleavage of
A with acidic KMnO4, two fragments are obtained. One fragment is acetic acid,
CH3CO2H, and the other fragment, C, is an optically active carboxylic acid. Show the
reactions, and propose structures for A, B, and C.
Note: The work here is to be done in 16 groups of equal size. One question for each group and
Question 10, 11 and 12 will be done by every group.
