Chem 334 - Fall 1998 - Organic Chemistry I
Portland State University - Dr. Carl C. Wamser

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Chapter 4 Quiz

1. (2 points each) Give a complete IUPAC name for each compound below, including designation of stereochemistry if it is specifically shown.

a)

(S)-6-chloro-2,3,3-trimethylheptane

b)

(S)-1,1-dibromo-3-chloro-3-methylcyclopentane

c)

(1R,2S)-1-bromo-2-fluoro-1-methylcyclohexane

d)

(S)-2-methylbicyclo[2.2.1]heptane

2. (2 points) A new drug is prepared so as to create mainly the (R)(+) enantiomer. The actual synthesis gives a product with an optical purity of 95%. If the specific rotation of optically pure material is +20°, what is the specific rotation of the synthesized sample? What is the composition of the synthesized sample in terms of percentage (R) and (S)?

[a] = + 19°

97.5% (R) + 2.5% (S)