W03 problems9b key

W03 problems9b key - 1. NaSCH 3 2. H 3 O + workup H 3 O +...

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O H O O H O KOH O NaOEt H H O 1. H 3 O + I EtO OEt O O 1. H 3 O + O O Problem Set 9 (Chapter 19 Enolate and Enamine) TA: Danny Ng 3/10/2003 1. Provide the missing reagents or products in the following reactions. Draw the structures of all possible enantiomers or diastereomers whenever applicable. a) 2. heat b) 2. heat c) 1. NaOH 2. H 3 O + 3. heat d) 1. LDA 2. 1. KO t Bu 2. e) 3. H 3 O + workup 1. NaOEt 2. H 3 O + workup 1. NaOEt 2. 1-iodopentane O H O Ph O Ph O O O O O O O O HO O HO O O O OEt O O OEt O
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O O Na OEt O O OH O N TA: Danny Ng 3/10/2003 Problem Set 9 2. Show how the following compounds can be synthesized by the Acetoacetic Ester Synthesis or the Malonic Ester Synthesis. 3. Provide the missing products.
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Unformatted text preview: 1. NaSCH 3 2. H 3 O + workup H 3 O + workup 1. PhMgBr 2. H 3 O + workup 1. 2. H 3 O + workup O OEt O 1. NaOEt 2. 3. NaOH 4. H 3 O + , warm I EtO O OEt O 1. NaOEt 2. 3. NaOH 4. H 3 O + , warm OTs O O OEt O OH Ph O SCH 3 O N O O TA: Danny Ng 3/10/2003 Problem Set 9 4. For the following reaction: (a) Provide the structure for the Compound A. (b) Provide the reaction mechanism. O Compound A 1. KOH 2. H3O + workup 3. heat O O O H OH O O O O O O Michael Addition O O Aldol proton transfer O OH H OH O Dehydration...
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W03 problems9b key - 1. NaSCH 3 2. H 3 O + workup H 3 O +...

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