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CHEM2213 Topic 10a.docx

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Chemistry 1027A/B
Mark Workentin

Topic 10a Carboxylic Acids What Are Carboxylic Acids?  Functional group of a carboxylic acid is a carboxyl group (carbonyl + hydroxyl = COOH)  Aliphatic carboxylic acid – RCOOH  Aromatic carboxylic acid – ArCOOH What Are The Physical Properties Of Carboxylic Acids?  Significantly higher boiling points than other types of organic compounds  Result from their polarity and from the fact that they form very strong intermolecular H bonds  Also interact with water molecules by H bonding through both their C=O and OH groups  more soluble in water  Hydrophilic carboxyl group increases water solubility while hydrophobic hydrocarbon chain decreases water solubility What Are The Acid-Base Properties Of Carboxylic Acids?  Carboxylic acids are weak acids  Stronger acids than alcohols because resonance stabilizes carboxylate anion by delocalizing its negative charge  React with NaOH, KOH, and other strong bases to form water-soluble salts How Are Carboxyl Groups Reduced?  Most resistant to reduction, not affected by catalytic reduction 2H /M)  Lithium aluminum hydride (LiAlH )4reduces carboxylic acid to a primary alcohol o Initial product is an aluminum alkoxide, which is then treated with water to give the 1° alcohol and LiOH + Al(OH) 3  Catalytic hydrogenation does not reduce carboxyl groups but does reduce alkenes to alkanes o Therefore, we can use H /M 2o reduce the functional group selectively in the presence of a carboxyl group  It is possible to reduce an aldehyde / ketone carbonyl group selectively in the presence of carboxylic group via NaBH 4 What Is Fischer Esterification?  Treatment of a carboxylic acid with an alcohol in the presence of an acid catalyst gives an ester  Acid-catalyzed esterification is reversible  In the Fischer esterification, the –OR portion of an alcohol replaces the – OH portion of a carboxylic acid  After addition of a nucleophile to a carbonyl, one possible mechanism is for the tet
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