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1) Define all chiral centers as either R or S. (12 Points)

Organic Chemistry

Test #2

100 Points


2) Define the following pairs of molecules as Diastereomers, Enantiomers or the same. (9 points)


3) Synthesize 2R 2-pentanol from 2R 2-Bromopentane. You can use any other reagents you want. (7 points)

4) How many stereoisomers are possible for the following molecule? (4 points)

5) Draw the enantiomer and a diastereomer of the following molecule. (6 points)


6) A mixture of two enantiomers (below) were looked at in a polarimeter. It read

+12 o


] S-3-hexanol = +24



] R-3-hexanol = -24

0 a) What was the enantiomeric excess of this solution? (4 points) b) What is the total percentage of each enantiomer? (4 points)

7) Draw both chair forms of trans-1,2-dibromocyclohexane (5 points)

8) Circle the structure in question 7 that has the lowest energy. (2 points)

9) For each structure: a) Put an asterisk (*) beside each chiral carbon. (5 points) b) Is the molecule chiral, non-chiral or meso? (6 points)


9) Draw the mechanism and the product for the following reaction. . (Make sure your arrows are pointed exactly where they should be and the you include all lone pairs of electrons) (5 points)

10) Design a synthesis of (R) 2-methoxy heptane from (S) 2-chloroheptane. (You can use any other reagents you need). (5 points)

11) Circle the solvent(s) from the selection below which would be considered protic

(6 points)


12) Which of the following reactions would go faster A or B? Explain Why. (5 points)

13) Fill-in the appropriate reagent, product, starting material (12 points)

14) Define the following (3 points)

Nucleophile –

Electrophile -