Carboxylic Acids

contain a carbonyl and hydroxyl group connected to the same carbon; always terminal groups; polar and hydrogen bond very well resulting in high boiling points; often exist as dimers in solution; acidity is enhanced by resonance between its oxygen atoms and substituents that are electron withdrawing; acidity decreased by substituents that are electron donating

carboxylic acids that have an α-hydrogen that is highly acidic

common reaction carboxylic acids; after opening the carbonyl via nucleophilic attack and forming a tetrahedral intermediate, the carbonyl can reform, thereby kicking off the leaving group; nucleophilic molecule replaces the leaving group of an acyl derivative; reactions are favored by a good leaving group

encompass all molecules with a carboxylic acid-derived carbonyl, including carboxylic acids, amides, esters, and anhydrides

nucleophilic acyl substitution: is formed if nucleophile is ammonia or amine

nucleophilic acyl substitution: is formed if nucleophile is an alcohol

nucleophilic acyl substitution: is formed if nucleophile is another carboxylic acid

nucleophilic acyl substitution reaction:

strong reducing agent that can be used to reduce carboxylic acids to a primary alcohol; NaBH4 (sodium borohydride) is not strong enough

spontaneous loss of carbon as carbon dioxide when heating by β-dicarboxylic acids and other β-keto acids; reaction proceeds via six-membered cyclic intermediate

decarboxylation mechanism:

mixing long-chain carboxylic acids (fatty acids) with a strong base results in formation of a salt we call soap

contain hydrophilic carboxylate heads and hydrophobic alkyl chain tails; organize in hydrophilic environments to from micelles

dissolves nonpolar organic molecules in its interior, and can be solvated with water due to its exterior shell of hydrophilic groups