ogo 1 exam 3 - . I. (32 points) Name_ Page 1 F.09.210E3 A....

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. Name_____________________________ I. (32 points) Page 1 F.09.210E3 A . The following reaction forms two major products, D and E . Draw Product E in the box provided indicating stereochemistry with lines, dashes and wedge bonds where appropriate. Product E H 3 C H 3 C H H OCH 3 Cl B . The relationship between these compounds is that they are: (circle all that apply) enantiomers diastereomers regioisomers a racemic mixture C . Use curved-arrow notation to draw the mechanism for the formation of Product D . Use lines, wedges and dashed wedges to indicate stereochemistry as needed. You may use "B:" as a general base if needed. H 3 C Cl 2 CH 3 OH CH 3 H Cl Cl H 3 C H 3 C H Cl H OCH 3 H 3 C H 3 C H Cl O CH 3 H B H 3 C H 3 C H Cl OCH 3 +4 rxn of Cl 2 +4 chloronium ion intermediate +4 attack of methanol +4 oxonium ion intermediate +4 deprotonation +4 pts correct stereochemistry throughout -2 transcription error carried throughout all arrows needed for each mechanistic step H H H 4 H 3 C Cl 2 CH 3 OH CH 3 H H Product D H 3 C H 3 C H H OCH 3 Cl + 24 4 H 0 pts for regioisomer, then 4 pts for "regioisomer" on Part B
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Name_____________________________ II. (20 points) Page 2 F.09.210E3 CH 3 H 3 C HOBr NaH B hint: A and B are diastereomers (S) (R) Br HO H (S) (S) O H 4 4 4 + enantiomer + enantiomer + H 2 and NaBr You have learned several different reactions that can result in the formation of the same functional group, but with different regiochemistry or stereochemistry. Here is another example of two ways to create compounds
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This note was uploaded on 03/01/2010 for the course CHEM 210 taught by Professor Capolla during the Fall '07 term at University of Michigan.

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ogo 1 exam 3 - . I. (32 points) Name_ Page 1 F.09.210E3 A....

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