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 acarboxylic acid. Chromic acid is a suitable oxidizing agent.(b)Aldehydes may be oxidized to carboxylic acids by any of the oxidizing agents that convertprimary alcohols to carboxylic acids.(c)The starting material has the same number of carbon atoms as does butanoic acid, and so allthat 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 thedesignated starting material, 1-butene.Hydroboration–oxidation of 1-butene yields 1-butanol, which can then be oxidized to butanoicacid 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.