Dolbier HW Solutions 381

Dolbier HW Solutions 381 - active site. Conjugate addition...

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This enolate adds to the carbonyl group of benzaldehyde to give the mixed aldol addition product, which then dehydrates under the reaction conditions. ( c ) The enolate of cyclohexanone adds to benzaldehyde. Dehydration of the mixed aldol addition product takes place under the reaction conditions to give the following mixed aldol condensa- tion product. 18.14 Mesityl oxide is an a , b -unsaturated ketone. Traces of acids or bases can catalyze its isomerization so that some of the less stable b , g -unsaturated isomer is present. 18.15 The relationship between the molecular formula of acrolein (C 3 H 4 O) and the product (C 3 H 5 N 3 O) corresponds to the addition of HN 3 to acrolein. Because propanal (CH 3 CH 2 CH ? O) does not react under these conditions, the carbon-carbon, not the carbon-oxygen, double bond of acrolein is the re-
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Unformatted text preview: active site. Conjugate addition is the reaction that occurs. N 3 CH 2 CH 2 CH O O H 2 C CHCH NaN 3 acetic acid Acrolein 3-Azidopropanal O CHCCH 3 C H 3 C H 3 C Mesityl oxide; 4-methyl-3-penten-2-one (more stable) O CH 2 CCH 3 C H 3 C H 2 C 4-Methyl-4-penten-2-one (less stable) HO 2 1 O Cyclohexanone O C 6 H 5 CH Benzaldehyde 1 H 2 O O CHC 6 H 5 Benzylidenecyclohexanone O 2 O C 6 H 5 CHCH 2 CC(CH 3 ) 3 1 Enolate of tert-butyl methyl ketone CH 2 CC(CH 3 ) 3 2 O Benzaldehyde OH O C 6 H 5 CHCH 2 CC(CH 3 ) 3 Product of mixed aldol addition O C 6 H 5 CH H 2 O O C 6 H 5 CH CHCC(CH 3 ) 3 4,4-Dimethyl-1-phenyl-1-penten-3-one (product of mixed aldol condensation) 2 H 2 O ENOLS AND ENOLATES 475...
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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