14D_f08_finalB

14D_f08_finalB - Chemistry 14D Fall 2008 Final Exam Part B...

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Chemistry 14D Fall 2008 Final Exam Part B Page 1 Behold Memnogo, a fictional pharmaceutical that inhibits memory loss during organic chemistry final exams. In Part B of this final exam we explore various reactions that might be employed in the synthesis of this drug. Memnogo 1. (10) The first step in the synthesis of Memnogo is conversion of 3-phenylpropionic acid into the corresponding acid chloride. A chemist whose Chem 14D grade was not above average tried to achieve this transformation with HCl in CH 3 OH, but this reaction yielded an ester instead of an acid chloride. 3-Phenyl propionic acid Not formed Actual product Write the mechanism for the formation of the ester. 2. (7) The same Chem 14D dropout from question 1 tried to form the five-membered ring by reacting the acid chloride with methoxide ion. Like his previous failed attempt, this reaction also did not give the expected product. Not formed Actual product Write the actual product in the box above. Write the mechanism for its formation. O O Br Ph Ph OH O HCl CH 3 OH Ph Cl O Ph OCH 3 O Cl O NaOCH 3 CH 3 OH O
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Chemistry 14D Fall 2008 Final Exam Part B Page 2 Questions 3 and 4 refer to this successful reaction for the closure of the cyclopentanone ring of Memnogo. 3.
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This note was uploaded on 03/12/2012 for the course CHEM 14D taught by Professor Hardinger during the Winter '08 term at UCLA.

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14D_f08_finalB - Chemistry 14D Fall 2008 Final Exam Part B...

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