Chem112BPractice2

Chem112BPractice2 - O Problem 3 Propose a mechanism for the...

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Chem 112B Spring 2007 Practice Problems (03/16/07) Problem 1 (a) Predict the possible Diels-Alder reaction products C and D of the following reaction. What would you expect F to be? N N O O O Heat Heat O H H O O F A B C + D E (b) On the basis of your answer in (a), predict the final products of the following reaction upon prolonged heating. O Heat O X + Y Problem 2 Nitriles behave similarly to other carboxylic acid derivatives in many 1,2-addition reactions. Suggest a mechanism for the following transformation. O CN CN O O 1. NaOEt, EtOH 2. H 3
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Unformatted text preview: O + Problem 3 Propose a mechanism for the following transformation. N O CO 2 Et N O O NaH (Base) HCl H 2 O N enamine H N O Problem 4 Predict which of the following would be aromatic according to Hückel’s rules. Consider all possible tautomers . H O N N N H N N H 3 C CH 3 O O O N O CH 3 H 3 C Question 5 On the basis of resonance and aromaticity considerations, predict which of the following would have the lowest barrier to rotation about the indicated bond. O O...
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