HT2x-04 - H our Examination#2 Chemistry 302-302A...

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Hour Examination #2, Chemistry 302-302A, 2004 "Problems worthy of attack prove their worth by hitting back." Piet Hein (thanks to Josh Schulman) 1 (21 points). Devise syntheses for the following molecules. You may use any inorganic reagent, alcohols containing no more than three carbons, benzene, pyridine, thiophene, furan, and...need something else organic? Ask and we’ll tell you if you can use it. Mechanisms are not necessary. H 3 C OH O H 3 C (a) (b) (c) 2 (21 points). Provide detailed mechanisms for the following condensation reactions. You do not have to predict or explain stereochemistry for part (b). (a) O H H 3 C CH 3 O NaOEt HOEt (Ph-CHO) Ph O Ph (b) O H CH 3 CH 2 CH 2 CH 3 O NaOEt HOEt (Ph-CHO) O O CH 3 H 3 C Ph Ph (c) Now explain why the two reactions take different routes.
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3 (18 points). You will have to analyze and think about what steps happen when in this problem. That is, the order in which you do things is very important. Provide mechanisms for the following transformations. In answering this question, you do not have to draw out the entire molecule over and over. Focus on the relevant parts.
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