Carboxylic Acids - Reactions Acid-base reactions: LDF H-bonding ion + NaOH Na+ + H2O octanoic acid sodium octanoate + water insoluble in H2O soluble dipole

Reactions Reduction: 5-oxo hexanoic acid 1,5- hexanediol 5-hydroxy LiAlH4 6 5 4 3 2 1 5-oxo hexanoic acid 1,5- hexanediol H2/ Pt NaBH4 5-hydroxy hexanoic acid

Reactions nucleophilic substitution condensation reaction reverse = + + H2O carboxylic acid alcohol ester condensation reaction reverse = hydrolysis H+ + ester + H2O carboxylic acid alcohol

Esters from alcohol from acid name = alkyl group from alcohol (yl) acid name changed to “oate” methyl butanoate apple pentyl butanoate peaches

Esters H-bond acceptors O O no H-bond donor dipole-dipole interactions water soluble low b.p.

Carboxylic acids nucleophilic substitution condensation reaction .. activator + + H2O carboxylic acid amine amide condensation reaction carboxylic acid + amine amide + H2O hydrolysis reaction amide + H2O carboxylic acid + amine

Amines N- H+ organic analogs of ammonia ammonia 1o amine 2o amine all have H-bond acceptor N- 1o and 2o have H-bond donor H+ high b.p. electronegativity O N liquid at room T > gas at room T

Amines nomenclature 1. Name and alphabetize R groups and add “amine” methylamine 1o ethyl methyl amine 2o ethyl dimethyl amine 3o low b.p.

Amines + H2O + OH- [R-NH3+] [OH-] smaller Kb weaker base Kb = [R-NH2] weak bases + H2O + OH- [R-NH3+] [OH-] smaller Kb weaker base Kb = [R-NH2]

Amines Condensation reaction nucleophilic substitution +H2O +H2O activator +H2O +H2O no reaction + amide carboxylic acid 2o amine 1o amine 3o amine amide Condensation reaction

Amides C-O and C-N double bond character very high b.p. C-O and C-N double bond character no rotation about C-O or C-N bonds molecule is flat and rigid structure of proteins