know the structures of the various members of the carboxyl family:
carboxylic acid, acid anhydride, ester, acid halide, amide, nitrile
know the common names up to C4 for the mono and dicarboxylic acids
formic, acetic, propionic, butyric
oxalic, malonic, succinic
understand the reasons for the acidity of the carboxylic acid group (pKa ~ 5)
resonance delocalization of the carboxylate anion
electron withdrawal effects increase acidity
recognize the relative order of reactivity expected for the carboxyl
derivatives
(leaving group effects)
recognize the distinctions between nucleophilic addition to carbonyls and nucleophilic substitution on carboxyls (same tetrahedral intermediate)
be able to name all the various carboxyl derivatives
be able to apply the list of functional group priorities (Table, page 533)
write products from nucleophilic substitutions on carboxyl derivatives:
interconversions of the different derivatives
conversions via the acid halide
hydrolysis to the carboxylic acid
Fischer esterification
write products from hydride reductions of carboxyl derivatives:
carboxylic acids or esters ---> alcohols
amides or nitriles ---> amines
write products from Grignard reactions with carboxyl derivatives:
esters ---> 3° alcohols
nitriles ---> ketones
write mechanisms for nucleophilic substitution reactions, with acid or base catalysis
create a synthetic sequence to prepare a given target molecule,
especially including Grignard additions