W03 problems9a key

W03 problems9a key - a) b) + + c) + H O O O i) KOH H O...

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H O H O H O H O Ph H O O O O Ph H O O Ph H O OEt O OEt O Ph H O O Ph OH O O Ph H O OEt O O H O OEt O Ph OH Ph H O OH H O OEt O Ph Problem Set IX 1. Provide the expected products for the reactions below. Winter 2003 The Aldol Reaction and Variations a) NaOH / H 2 O + NaOH / H 2 O b) c) + d) NaOH / H 2 O Aldol i) KOH ii) EtI e) i) LDA ii) EtI f) i) KOH ii) i) LDA g) ii) Kinetic vs Thermodynamic Enolates NaOEt / EtOH NaOEt / EtOH + h) i) Claisen 2 2
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OEt O O OEt O O O EtO OEt O O HO O H O O Br H O NaOH O H O LDA NaOEt EtO OEt O O H O Ph O Ph O Ph EtO OEt O O HO OH O O H 3 O + H 3 O + OH O O OEt O O Problem Set IX Winter 2003 The Aldol Reaction and Variations Acetoacetic Ester Synthesis i) NaOEt ii) CH 3 CH 2 Br i) NaOEt ii) CH 3 CH 2 CH 2 Br j) Malonic Ester Synthesis i) NaOEt ii) CH 3 CH 2 Br i) NaOEt ii) CH 3 CH 2 CH 2 Br k) 2. Provide the necessary reagents or the products for the following transformations.
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Unformatted text preview: a) b) + + c) + H O O O i) KOH H O NaOEt ii) CH 3 CH 2 CH 2 CH 2 Cl H O O i) LDA ii) O OMe O H O O O OEt O NaOEt H O O KOH H H O Br KOH Ph H O NaOEt OEt O H O O H OH Ph H O O O O H O O O Ph OH Problem Set IX Winter 2003 The Aldol Reaction and Variations d) + e) f) g) h) i) i) i) i) 1. NaOMe 2. MeI 3. H 3 O + 4. i) KOH ii) O H O O O O OH O O O H O O O O O Ph 3 P H O H H O H H O Problem Set IX 3. Retrosynthetic analysis. Winter 2003 The Aldol Reaction and Variations...
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W03 problems9a key - a) b) + + c) + H O O O i) KOH H O...

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