Dolbier HW Solutions 482

Dolbier HW Solutions 482 - carboxylate Diethyl...

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CHAPTER 21 ESTER ENOLATES SOLUTIONS TO TEXT PROBLEMS 21.1 Ethyl benzoate cannot undergo the Claisen condensation, because it has no protons on its a -carbon atom and so cannot form an enolate. Ethyl pentanoate and ethyl phenylacetate can undergo the Claisen condensation. 21.2 ( b ) The enolate formed by proton abstraction from the a -carbon atom of diethyl 4-methylhep- tanedioate cyclizes to form a six-membered b -keto ester. CH 3 CH 2 OCCH 2 CH 2 CHCH 2 CH 2 COCH 2 CH 3 CH 3 O O CH 3 CH 2 O NaOCH 2 CH 3 OCH 2 CH 3 CH 3 O O C Ethyl (5-methyl-2-oxocyclohexane)-
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Unformatted text preview: carboxylate Diethyl 4-methylheptanedioate OCH 2 CH 3 O O C C H 2 C CHCH 3 CH 2 CH 2 CH 2 2C 6 H 5 CH 2 COCH 2 CH 3 O Ethyl phenylacetate Ethyl 3-oxo-2,4-diphenylbutanoate C 6 H 5 CH 2 CCHCOCH 2 CH 3 O O C 6 H 5 1. NaOCH 2 CH 3 2. H 3 O 1 2CH 3 CH 2 CH 2 CH 2 COCH 2 CH 3 O Ethyl pentanoate Ethyl 3-oxo-2-propylheptanoate CH 3 CH 2 CH 2 CH 2 CCHCOCH 2 CH 3 O O CH 2 CH 2 CH 3 1. NaOCH 2 CH 3 2. H 3 O 1 576...
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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