Dolbier HW Solutions 484

Dolbier HW Solutions 484 - O 1. NaOCH 2 CH 3 2. HO 2 , H 2...

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578 ESTER ENOLATES 21.5 The desired ketone, cyclopentanone, is derived from the corresponding b -keto ester. This key intermediate is obtained from a Dieckmann cyclization of the starting material, diethyl hexanedioate. First treat the diester with sodium ethoxide to effect the Dieckmann cyclization. Next convert the b -keto ester to the desired product by saponi f cation and decarboxylation. 21.6 ( b ) Write a structural formula for the desired product; then disconnect a bond to the a -carbon atom. Therefore 1 CH 2 CH 2 CCH 3 O 4-Phenyl-2-butanone Benzyl bromide CH 2 Br Ethyl acetoacetate CH 3 CCH 2 COCH 2 CH 3 O
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Unformatted text preview: O 1. NaOCH 2 CH 3 2. HO 2 , H 2 O 3. H 1 4. heat CH 2 CH 2 CCH 3 O 1 Required alkyl halide CH 2 X Derived from ethyl acetoacetate CH 2 CCH 3 O 2 COCH 2 CH 3 O O Ethyl (2-oxocyclopentane)-carboxylate O Cyclopentanone 1. HO 2 , H 2 O 2. H 1 3. heat CH 3 CH 2 OCCH 2 CH 2 CH 2 CH 2 COCH 2 CH 3 O O 1. NaOCH 2 CH 3 2. H 3 O 1 COCH 2 CH 3 O O Ethyl (2-oxocyclopentane)-carboxylate Diethyl hexanedioate CH 3 CH 2 O 2 C(CH 2 ) 4 CO 2 CH 2 CH 3 O COCH 2 CH 3 O O O O H 3 C 1 2 OCH 2 CH 3 O O 2 H 3 C CH 3 CH 2 O 2-Methyl-1,3-cyclopentanedione...
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