Dolbier HW Solutions 419

Dolbier HW Solutions 419 - 513 CARBOXYLIC ACIDS...

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electronegative than nitrogen and so stabilizes the carboxylate anion better. Furan-2- carboxylic acid is a stronger acid than pyrrole-2-carboxylic acid. 19.17 ( a ) The conversion of 1-butanol to butanoic acid is simply the oxidation of a primary alcohol to a carboxylic acid. Chromic acid is a suitable oxidizing agent. ( b ) Aldehydes may be oxidized to carboxylic acids by any of the oxidizing agents that convert primary alcohols to carboxylic acids. ( c ) The starting material has the same number of carbon atoms as does butanoic acid, and so all that is required is a series of functional group transformations. Carboxylic acids may be ob- tained by oxidation of the corresponding primary alcohol. The alcohol is available from the designated starting material, 1-butene. Hydroboration oxidation of 1-butene yields 1-butanol, which can then be oxidized to butanoic acid as in part ( a ). ( d ) Converting 1-propanol to butanoic acid requires the carbon chain to be extended by one atom.
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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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