2010 che 230 exam 3 solutions - Department of Chemistry - Illinois ...
2010 che 230 exam 3 solutions - Department of Chemistry - Illinois ...
2010 che 230 exam 3 solutions - Department of Chemistry - Illinois ...
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16. The specific rotation <strong>of</strong> an impure solution is [α] D -200 o . The enantiomerically pure (S)-enantiomer<br />
related to this solution rotates light with an [α] D +500 o . What is the percent composition <strong>of</strong> the mixture<br />
(40 pts) There is no partial credit for this problem.<br />
70%(R)<br />
30%(S)<br />
17. Consider the following molecules.<br />
1 2 3 4<br />
1 and 2 and 1 and 4 are diastereomers (20 pts)<br />
1 and 3 are enantiomers (20 pts)<br />
2 and 4 represent a meso-compound (20 pts)<br />
18. Show the reaction products, the complete reaction mechanism, and postulated transition state for the<br />
following reaction. You must address the stereo<strong>che</strong>mical consequences <strong>of</strong> the reaction. (80 pts)<br />
See class notes for this SN2 reaction mechanism.<br />
19. Provide the major substitution products and detailed reaction mechanisms for the reactions that are listed<br />
below. The mechanism must be drawn out completely. (80 pts)<br />
See class notes for this SN1 reaction mechanism.<br />
20. Describe in detail the two forces that stabilize a carbocation. Use the molecular structure that is drawn<br />
below to help your explanation. (20 pts)<br />
© <strong>2010</strong> Pr<strong>of</strong>. S. R. Hitchcock, <strong>Department</strong> <strong>of</strong> <strong>Chemistry</strong>, <strong>Illinois</strong> State University, Normal, IL 61790-4160 4
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