Dolbier HW Solutions 416

Dolbier HW Solutions 416 - bonyl compound that yields a...

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( g ) A carboxylic acid function is attached as a substituent on a seven-membered ring. The com- pound is cycloheptanecarboxylic acid. ( h ) The aromatic ring is named as a substituent attached to the eight-carbon carboxylic acid. Numbering of the chain begins with the carboxyl group. 19.15 ( a ) Carboxylic acids are the most acidic class of organic compounds containing only the elements C, H, and O. The order of decreasing acidity is K a p K a Acetic acid CH 3 CO 2 H 1.8 3 10 2 5 4.7 Ethanol CH 3 CH 2 OH 10 2 16 16 Ethane CH 3 CH 3 < 10 2 46 < 46 ( b ) Here again, the carboxylic acid is the strongest acid and the hydrocarbon the weakest: K a p K a Benzoic acid C 6 H 5 CO 2 H 6.7 3 10 2 5 4.2 Benzyl alcohol C 6 H 5 CH 2 OH 10 2 16 10 2 18 16 18 Benzene C 6 H 6 < 10 2 43 < 43 ( c ) Propanedioic acid is a stronger acid than propanoic acid because the electron-withdrawing effect of one carboxyl group enhances the ionization of the other. Propanedial is a 1,3-dicar-
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Unformatted text preview: bonyl compound that yields a stabilized enolate; it is more acidic than 1,3-propanediol. K a p K a Propanedioic acid HO 2 CCH 2 CO 2 H 1.4 3 10 2 3 2.9 Propanoic acid CH 3 CH 2 CO 2 H 1.3 3 10 2 5 4.9 Propanedial O ? CHCH 2 CH ? O < 10 2 9 < 9 1,3-Propanediol HOCH 2 CH 2 CH 2 OH < 10 2 16 < 16 ( d ) Tri f uoromethanesulfonic acid is by far the strongest acid in the group. It is structurally related to sulfuric acid, but its three f uorine substituents make it much stronger. Fluorine substituents 6-Phenyloctanoic acid CH(CH 2 ) 4 CO 2 H CH 2 CH 3 CO 2 H 510 CARBOXYLIC ACIDS __ __ __...
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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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