Chem 336 - Spring 2002
Organic Chemistry III
Dr. Carl C. Wamser
know the structures of the various members of the carboxyl family:
carboxylic acid, acid anhydride, ester, acid halide, amide, nitrile,
lactone, lactam, imide, acyl group
know the common names up to C4 for the mono and dicarboxylic acids
formic, acetic, propionic, butyric
oxalic, malonic, succinic
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 (similar tetrahedral intermediate)
write names for the various carboxyl derivatives
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