Lecture 23 Claisen Condensation

Lecture 23 Claisen Condensation - What are the products?...

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What are the products? O O O O H H-Bond heat O H O β -Dicarbonyl Compounds Chapter 19 Bad news: Long Chapter Good news: Not much new What are the products? O O O O H H-Bond O C O H + heat O O H O O + CO 2 O + CO 2 O O O H O O O H O C O O H + O + O OH O + O O H O C O O + OH C O O + A B C D Decarboxylation of acids with a β -carbonyl Intro to Chapter 19 O O O O H H-Bond O C O H + heat O + CO 2 O H α β γ O O β -ketoacid O O HA O + CO 2 O C O + heat O O β -ketocarboxylate O O O O H H O O O O H H O O C O O H + H heat HO O + CO 2 malonic acid Which is most acidic? OO O pKa = 17 19 25 H 3 C H H 3 C CH 3 H 3 C O CH 3 A B C pKa = 9 11 13 H 3 C O CH 3 O H 3 C O O O O O O O CH 3 H 3 C CH 3 A B C O O O O H O Draw the best representation of the immediate (initial) product of the deprotonation reaction. O O O O O O O O O A B C O O O D E F O O O O O H O O O 4. Heat O O O O Step 3. Add more acid and cook it a bit O O O H O O O 2. H + O O O O Claisen O Condensation Formation of this anion is the driving force for the reaction
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O O O O O No acidic hydrogen at alpha position.
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Lecture 23 Claisen Condensation - What are the products?...

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