Problem_Set_9___solution - Chem 3580 - Spring 2009 Problem...

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1 Chem 3580 - Spring 2009 Problem Set 9 - Solution 1. OEt O O OEt O O EtO OEt O + O OEt OEt O + O OEt EtO O OEt O O EtO OEt O O O EtO O O + O OEt EtO O O + O OEt EtO O O OEt H + Ethyl acetoacetate stable anion Ethyl acetoacetate 2. O O H H (a) N CH 3 H H O O H H N H H CH 3 O OH H H N H CH 3 O OH 2 H H N H CH 3 proton transfer H—OH 2 O H H N H CH 3 H OH 2 O H N H CH 3 N CH 3 H O N CH 3 HO proton transfer N CH 3 H 2 O N H H 2 O H 2 O—H (show detals) (show detals) imine-enamine isomerization O O Et 3 N H O O O Et 3 N H OH O + (b) Et 3 N Et 3 N
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2 OEt OEt O O O O (c) H EtO OEt OEt O O OEt OEt O O OEt OEt O O EtO O OEt OEt O O O H OEt H Double Claisen O OEt EtO You may show separately O H OEt OEt OEt O O O O H—OH 2 H—OH 2 OEt OEt O O H 3 O + acid-catalyzed hydrolysis You should be able to write a detailed mechanism here O O O O O O H H O O H O O Decarboxylation Keto-enol equilibrium H Double Claisen Product 3. MeO
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Problem_Set_9___solution - Chem 3580 - Spring 2009 Problem...

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