Problem_Set_9 - CHO + OEt O O Ph OEt O O Ph O O OEt OEt O O...

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1 Chem 3580 - Spring 2009 Problem Set 9 1. Provide a plausible mechanism for the reaction shown below. Provide a reason for why the reaction goes in the direction of the arrow and why one full equivalent of base is used. Claisen reaction is reversible. OEt O O 1. EtO 2. H + OEt O O OEt O 2 1 2. Propose a plausible mechanism for each of the following reactions. O O H H + CH 3 NH 2 N H + (a) H O + O OH O Et 3 N (b) OEt OEt O O 1. EtO , EtOH 2. H 3 O + , ! O O (c) 3. Propose a practical laboratory synthesis of the compounds shown below from the indicated starting compounds. Unless otherwise restricted, you may use any necessary inorganic reagents and, where appropriate, other organic reagents containing no more than 4 carbon atoms. EtO O MeO O O Ph from (a) EtO OEt O O OH O from (b)
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2 from O Only source of carbon (c) EtO OEt O O O from OH H H O O Only sources of carbon. (d) from O (e) O O from O (f) 4. Provide the missing experimental conditions in the synthetic scheme shown below.
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Unformatted text preview: CHO + OEt O O Ph OEt O O Ph O O OEt OEt O O 1 2 Ph O O 3 5. Provide the structures for products A-D. NH 2 + OMe O A Br OMe O B 1. MeO , MeOH 2. H 3 O + C 1. HO , H 2 O 2. H 3 O + , ! D NaBH 4 N OH 3 6. Claisen condensation can be used to synthesize ketones as shown in the scheme below. Write down the structures for A-C. OEt O 1. EtO , EtOH 2. H 3 O + A HO , H 2 O, ! B H 3 O + , ! C (C 9 H 18 O) 7. Provide the structures for A and C. O O OEt EtO + O EtONa (cat) EtOH A 1. EtONa (1 equiv) EtOH O CO 2 Et O 1. HO , H 2 O, ! 2. H 3 O + B 2. H 3 O + , ! C 8. Provide the structures for A and B. Suggest a mechanism for the formation of A and B. O H EtONa, EtOH H OEt O (exs) A O t-BuOK B KOH, H 2 O O H...
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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Problem_Set_9 - CHO + OEt O O Ph OEt O O Ph O O OEt OEt O O...

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