acidsg - Copyright, Arizona State University The Organic...

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Carboxylic Acids 1 Copyright, Arizona State University Copyright, Arizona State University Carboxylic Acids The Organic Acids (more. ..) Notation: Acids and their conjugate bases Carboxylic Acid Carboxylate Anion -H C R O OH C R O O 1 Nomenclature IUPAC priority: acid > aldehyde> ketone> alcohol > alkene > alkyne > halide • priority increases with increasing oxidation state, acids is most oxidized, always highest priority • carbon carrying the -CO 2 H is number 1 • suffix "-oic acid" Examples H 3 C CO 2 H ethanoic acid (acetic acid, non-IUPAC) 1 2 C C CH 3 O OH H 3 C CH 3 1 2 3 2,2-dimethylpropanoic acid O OH O 2 N p -nitrobenzoic acid 2 3 4-oxohexanoic acid CO 2 H O 1 4 5 6 2 Factors Controlling Acidity • comparing acidity - think about acidity as a "chemical reaction" determined by stabilities of conjugate base anions H–Z H + + Z H–Y H + + Y which is stronger acid? Examples • what are the pKa's of some carboxylic acids (in comparison to acetic acid)? CO 2 H H CO 2 H O 2 N CO 2 H CO 2 O 2 N H + + H + + 4.2 3.4 CH 3 CO 2 H ClCH 2 CO 2 H 4.8 3.9 H + + H + + CH 3 CO 2 ClCH 2 CO 2 anion weakly stabilized by –Cl ( inductive effect) CF 3 CO 2 H 0.3 3.6 H + + H + + CF 3 CO 2 MeO CO 2 MeO CO 2 H anion strongly stabilized by –CF 3 anion weakly stabilized by –OMe ( inductive only, no resonance here!) anion weakly stabilized by sp 2 carbon ( no resonance here!) anion further stabilized by –NO 2 ( inductive and resonance) CO 2 H MeO CO 2 MeO H + + 4.5 anion weakly destabilized by -OMe (resonance) pKa acid conjugate base X
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Carboxylic Acids 2 Copyright, Arizona State University Copyright, Arizona State University Carboxylic Acid PROBLEMS Acid Nomenclature In each case, give the IUPAC name for the provided structure (ignore stereochemistry unless specified) 1 (easier) CH 3
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This note was uploaded on 01/07/2012 for the course CHM 234 taught by Professor Iangould during the Spring '12 term at Appalachian State.

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acidsg - Copyright, Arizona State University The Organic...

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