Lecture 36 - (24.6A Synthetically Useful Examples • Rxn...

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1 Reading for Wednesday Finish Chapter 24 ARIS Quiz #7 Available Now Due tonight at 11:59 PM Quiz #8 (final one) available thie Wednesday Mon. 6:00-7:30 pm MAL 3092 Tues. 2:30-4:00 PM MAL 2007 Wed. 5:00-6:30 PM MAL 2001 Thurs. 9:30-10:50 AM MAL 1003 Sat. 11:30 AM-1:00 PM MAL 2007 PLUS Sessions THIS WEEK Chapter 24 Carbonyl Condensation Reactions Claisen Reaction (24.5) Base-promoted reaction between two esters to form a β -keto ester An example of nucleophilic acyl substitution Claisen Reaction (24.5) Deprotonation in last step (before work-up) drives the reaction equilibrium. Evidence? No product in rxn. below.
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2 Crossed (Mixed) Claisen Rxn.
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Unformatted text preview: (24.6A) Synthetically Useful Examples • Rxn. between two esters, only one having α-H’s • Rxn. between a ketone and an ester • The ketone forms an enolate because it is more acidic Variations on the Crossed Claisen Rxn. (24.6B) • Using (EtO) 2 CO or ClCO 2 Et as electrophile The Dieckmann Reaction (24.7) • An intramolecular Claisen reaction • Products are 5- and 6-membered rings Application of the Claisen Reaction Vitamin K Pindone: *Vitamin K analogue used as a poison *interferes with blood coagulation role of Vitamin K O O O...
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