ut5-507a - CHEM 228 Section 507 UNIT TEST 5 1 1. a)...

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CHEM 228 Section 507 UNIT TEST 5 1 1. a) Indicate the most acidic hydrogen(s) in each compound below by circling them or drawing them in if they are not shown. (3 pts) OH O CH 2 C H O H 3 C C H 2 CH 3 O O I II III b) Rank the molecules above in order of increasing acidity ( least acidic to most acidic). Circle the letter corresponding to your answer. (2pts) a. III, II, I b. II, III, I c. I, II, III d. II, I, III c) Draw the structures for all enols of Compound II . (2 pts) 2. Consider the reaction sequence below to answer the following questions: 1. NaOEt, EtOH 2. H 3 O + 1. NaOEt, EtOH 2. BrCH 2 Ph H 3 O + heat A B Compound D + EtOH + CO 2 C CH 3 COEt O 2 H 3 C OEt O O H 3 C OEt O O CH 2 Ph a) Below are the structures and intermediates for the conversion of Compound B into Compound C . Draw arrows showing the electron flow in this conversion. (4 pts) H 3 C OEt O O H H O Et H 3 C OEt O O H PhH 2 C Br H 3 C OEt O O CH 2 Ph © Tammy H. Tiner, 2005
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CHEM 228 Section 507 UNIT TEST 5 2 2. b) Write the complete stepwise mechanism for the conversion of
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This note was uploaded on 04/15/2008 for the course CHEM 228 taught by Professor Tichy during the Spring '08 term at Texas A&M.

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ut5-507a - CHEM 228 Section 507 UNIT TEST 5 1 1. a)...

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