CHAPTER 19 - CHAPTER 19-DICARBONYL COMPOUNDS CLAISEN...

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CHAPTER 19 β -DICARBONYL COMPOUNDS - - CLAISEN CONDENSATION - - ACETOACETIC ESTER SYNTHESIS - - MALONIC ESTER SYNTHESIS - - OTHER ACTIVE HYDROGEN COMPOUNDS [ OMIT DETAILS OF SECTIONS 19.6 – 19.12 ]
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INTRODUCTION: - - 1,3 – DICARBONYL / β – DICARBONYL - - CAN THIS H BE PULLED OFF BY ( RO )? - - WHAT MIGHT HAPPEN IF THIS ENOLATE ION IS TREATED WITH R X ? - - p 879 CLAISEN CONDENSATION: - - p 879 - - cf. ALDOL CONDENSATION - - SEE p 880: ETHYL PENTANOATE - - MECHANISM : - - SEE p 880-882 - - EXAMINE FAVORABLE DIRECTION FOR THE VARIOUS STEPS C O C H C O pKa = 9 - 11 α β 1 2 3
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- - CAUTION: - - ALKOXIDE ANION: RO ( USED AS BASE ) SHOULD HAVE THE SAME “– R ” GROUP AS THE ESTER : – CO 2 R - - WHY ? - - TO AVOID TRANS- ESTERIFICATION - - COMPARE THE FOLLOWING SUBSTANCES: - - WHICH ONE DOES NOT UNDERGO CLAISEN CONDENSATION ? - - WHY ? - - SEE STEP 3 OF MECHANISM - - DO PROBLEM : 19.1 p 882 C H H C O OR R' C R'' H C O OR R'
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- - INTRAMOLECULAR CLAISEN - - DIECKMANN CONDENSATION - - p 883 - - EXAMINE POSITION OF EQUILIBRIUM
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CHAPTER 19 - CHAPTER 19-DICARBONYL COMPOUNDS CLAISEN...

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