CHAPTER 17 - CHAPTER 17 ALDOL REACTIONS - - ACIDITY OF...

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CHAPTER 17 ALDOL REACTIONS - - ACIDITY OF α – HYDROGENS - - REACTIONS VIA ENOLS, ENOLATES - - ALDOL REACTION - - CONJUGATE ADDITIONS
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ACIDITY OF α – HYDROGENS pKa 19-20 ( cf. pKa ALKANE HYDROGENS) - - WHY ? - - RESONANCE – STABILIZED ANION ENOLATE ” ION p. 771 - - IMPLICATIONS ? - - THE α CARBON IS A POTENTIAL Nu: ! KETO – ENOL EQUILIBRIUM: - - SIMPLE MONO CARBONYL COMPOUND: “ KETO FORM FAVORED - - WHY ? cf. π – BOND STRENGTH OF: ( C O ) v. ( C C ) ~ 364 kJ / mol ~250 kJ / mol - - p. 772 C H C O C H C H C H α α β γ
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HOWEVER: - - β - DICARBONYL : - - % ENOL IS HIGHER ! - - WHY ? p . 773 - - HYDROGEN BONDING - - 6-MEMBERED RING - - DO PROBLEM : 17.1 p. 773 REACTIONS VIA ENOLS, ENOLATES: - - RACEMIZATION : p. 773 - - DO PROBLEMS : 17.2 17.3 p. 774 - - HALOGENATION AT α CARBON - - SEE MECHANISMS p. 775, 776 [ cf. HALOGENATION OF ALKENES p. 350 ] - - HALOFORM REACTION p. 777 – 778 - - DETECTION OF METHYL KETONES ( CH 3 -CO- R ) - - HALOGENATION OF CH 3 , THEN CLEAVAGE TO GIVE:
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CHX 3 + R-CO 2
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CHAPTER 17 - CHAPTER 17 ALDOL REACTIONS - - ACIDITY OF...

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