Assignment 2-1
Assignment 2-1
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.
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
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?
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.