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E3,241b,S07 - EXAM 3 CHEMISTRY 241b April 5 2007 Dr...

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EXAM 3 CHEMISTRY 241b April 5, 2007 Dr. Spurgeon Answer Key __________________________________________________________________________________________ 1. (20 points) Complete the following reaction schemes by supplying the correct name of the starting material or structure of the product and then match the reaction with the list provided on the right (use lines to match the correct scheme with the correct reaction name). a. Diethyl malonate + bromocyclohexane b. Ethyl acetoacetate + c. Diethyl malonate + 5-methyl-2-cyclopentenone d. Product from reaction ‘c’ with vigorous H 3 O + and heat e. Ethyl acetoacetate + 1. NaOEt 2. H 3 O + , mild heat 1. NaOEt 2. very mild work-up (water even) 1. NaOEt 2. H 3 O + , heat 1. NaOEt 2. mild H 3 O + Malonic Ester Synthesis List of Reactions Aldol Michael Claisen Hydrolysis then Decarboxylation EtO CH 3 O O O CH 3 O O 2 N CH 3 O EtO O OMIT, the product is drawn incorrectly. p -nitrobenzaldehyde H 3 C O OEt O O H 3 C O OH O H 3 C O HO
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2. (14 points) The following products can be synthesized from the starting materials below. Show the complete reaction sequence (include all necessary reagents) to complete each synthesis.
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