CHEM1280 Problem Set 5

(Due on 31 Oct. 2012)

1. Name the following compounds using R,S and E,Z designations where necessary:

2. Draw the Fischer project for a diastereomer of following:

3. Indicate whether the following pairs of structures represent identical compounds,

enantiomers, diastereomers, or constitutional isomers:

4. Give the products that would be obtained from the reactions of cis-2-butene with each of
following reagents. If the products can exist as stereisomers, show which stereoisomers
are formed.
a. HCl b. H2O + H2SO4 c. H2, Pt/C

5. Draw the structures for each of the following:

a. (S)-1-bromo-1-chlorobutane
b. two achiral stereoisomers of (3S, 5S)-3,4,5-trimethylheptane

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6. Select a pair of enantiomers, a pair of conformers, and a pair of diastereomers from the
following Newman projections.

7. Draw the two chair conformers for each of the following, and indicate which conformer
is more stable:
a. cis-1-ethyl-3-methylcyclohexane c. trans-1-ethyl-3-methylcyclohexane
b. trans-1-ethyl-2-isopropylcyclohexane d. cis-1-ethyl-3-isopropylcyclohexane

8. Using Newman projections, draw the most stable conformation for the following:
a. 3-methylpentane, considering rotation about the C-2—C-3 bond
b. 3-methylhexane, considering rotation about the C-3—C-4 bond