Dolbier HW Solutions 384

Dolbier HW Solutions 384 - drogen bonding. ( d ) The enol...

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18.21 ( a ) 2-Methylpropanal has the greater enol content. Although the enol content of 2-methylpropanal is quite small, the compound is nevertheless capable of enolization, whereas the other compound, 2,2-dimethylpropanal, cannot enolize it has no a hydrogens. ( b ) Benzophenone has no a hydrogens; it cannot form an enol. Dibenzyl ketone enolizes slightly to form a small amount of enol. ( c ) Here we are comparing a simple ketone, dibenzyl ketone, with a b -diketone. The b -diketone enolizes to a much greater extent than the simple ketone because its enol form is stabilized by conjugation of the double bond with the remaining carbonyl group and by intramolecular hy-
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Unformatted text preview: drogen bonding. ( d ) The enol content of cyclohexanone is quite small, whereas the enol form of 2,4-cyclo-hexadienone is the aromatic compound phenol, and therefore enolization is essentially complete. O Keto form OH Enol form (aromatic; much more stable) 1,3-Diphenyl-1,3-propanedione C 6 H 5 CCH 2 CC 6 H 5 O O Enol form O C 6 H 5 C CH CC 6 H 5 O H Dibenzyl ketone C 6 H 5 CH 2 CCH 2 C 6 H 5 O Enol form C 6 H 5 CH CCH 2 C 6 H 5 OH C O (Enolization is impossible.) C H CH 3 C CH 3 CH 3 O (Enolization is impossible.) 2-Methylpropanal (CH 3 ) 2 CHCH O Enol form (CH 3 ) 2 C CH OH 478 ENOLS AND ENOLATES...
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