12 Aldol 2011 SPRING - reaction Properly termed aldol...

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Click to edit Master subtitle style 4/27/11 Aldol Laboratory 10
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4/27/11 Formation of enols and enolates
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4/27/11 O OH O O H -H + -H + +H + +H + Tautomerization vs. Resonance Keto and enol forms are tautomers Different chemical species Two arrows => Equilibrium Two representation of an enolate Resonance forms that represent the same chemical species Double headed arrow and Brackets => Resonance [acid or base catalysis] Keto form Enol form Enolate
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4/27/11 Aldol condensation
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4/27/11 Base-catalyzed aldol mechanism
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4/27/11 Synthesis of trans -p- anisalacetophenone Properly termed “aldol addition
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Unformatted text preview: reaction Properly termed aldol condensation reaction 4/27/11 Cannizzaro disproportionation or Disproportionation 4/27/11 1HNMR of trans-p-500 MHz 4/27/11 Representative J-values 4/27/11 ,-unsaturated carbonyl chemical shifts 500 MHz 7.438 7.407 = 0.031 0.031 ppm x 500 MHz = 15.6 Hz 4/27/11 ,-unsaturated carbonyl chemical shifts 500 MHz 4/27/11 Aromatic proton chemical shifts 4/27/11 Aromatic proton chemical shifts 4/27/11 500 MHz Other coupling constants Large ca. 9 Hz (ortho) Small ca. 3Hz (meta)...
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12 Aldol 2011 SPRING - reaction Properly termed aldol...

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