CHE321, Exam 3 May 1, 2013

Library of Synthetic Reactions.

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 CHE321, Exam 3 May 1, 2013
Multiple Choice

1. Choose the major product of the following reaction. (class quiz)

2. Choose the reactants that would prepare the product of the following reaction sequence. (class quiz)

3. Choose the order that has the following compounds correctly arranged with respect to increasing acidity. (class
quiz)

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 CHE321, Exam 3 May 1, 2013
4. Predict the major product of the following reaction. (class quiz)

5. A professor wanted to prepare an amide by reacting benzoic acid with an amine, piperidine, using DCC.
Unfortunately, the professor stopped the reaction by adding water before it was complete and ended up with a
mixture of cyclohexylurea, benzoic acid and piperidine.. The product mixture was separated using the following
reaction scheme. Choose the letter where the carboxylic acid would be found. (class quiz)

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 CHE321, Exam 3 May 1, 2013
6. Choose the reaction that will not give the amine as shown. (class quiz)

7. Choose the order that has the following amines correctly arranged with respect to increasing basicity. (WS11
online quiz; q1)

8. Choose the order that has the following phenols correctly arranged with respect to increasing acidity. (class quiz)

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 CHE321, Exam 3 May 1, 2013
9. The following reaction gives a key intermediate for the synthesis of Tramadol, an analgesic used to treat severe
pain. Choose the structure of this intermediate. (class quiz pts)

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10. Choose the correct product of the following rearrangement. The reactant is labeled with C-isotope at the site
marked with an asterisk. (WS12 online quiz; q9)

Short Answer

11. Give the structure of the major product of the following set of reactions. 5 pts

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 CHE321, Exam 3 May 1, 2013
12. Give the product of the following reaction sequence. 5 pts (WS11 pt2; q4)

13. Give the product of the following reaction.

14. Give the major product of the following reaction, a key step in Woodwards synthesis of prostaglandin F2. (class
quiz, 5 pts) (J. Am. Chem. Soc., 1973, 95,6853)

15. Give compounds A and B in the following scheme used in the synthesis of Fentanyl. (class quiz, 10 pts)

16. Propose a mechanism for the following reaction. (class quiz, 10 pts)

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 CHE321, Exam 3 May 1, 2013
17. Benzphetamine is an appetite suppressant drug sold under the brand name Didrex. Propose a synthesis of
benzphetamine starting from benzene and any compound(s) containing three carbon atoms or less. 10 pts (WS11
pt2; q1)