Promblem Set #03 A - Chemistry 436 Professor Paul J....

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Chemistry 436 Professor Paul J. Hergenrother Spring 2009 University of Illinois, Urbana-Champaign Answers Problem set #3; Due February 13, 2009 1) Predict the products and draw out the mechanisms for the following reactions. All go via the standard aldol mechanism, as discussed in class. O LDA -78 o C H O O NaH room temp Br then H 2 O workup then H 2 O workup O O Et 3 Si-Cl Et 3 Si-Cl NaH room temp LDA -78 o C a) b) c) d) O KINETIC ENOLATE: It would be difficult to stop this at the β -hydroxy ketone product, as the product drawn is stabilized by extensive conjugation THERMODYNAMIC ENOLATE O OSiEt 3 KINETIC ENOLATE OSiEt 3 THERMODYNAMIC ENOLATE
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O From starting materials containing 5 or less carbons a) You should spot the 1,3-relationship between the double bond and the ether. We know that alkenes are easily derived from ketones. The ketone-containing compound can be easily derived from an aldol. Thus: 1 2 3 O O O O H O + In the forward direction: O LDA -78 o C O
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Promblem Set #03 A - Chemistry 436 Professor Paul J....

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