Organic Chemistry III

Professor Carl C. Wamser

Carboxyl Derivatives

Knowledge - Level 1

know the structures of the various members of the carboxyl family:

carboxylic acid, acid anhydride, ester, thioester, 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

Concepts - Level 2

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)

Applications - Level 3

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

Analytical Skills - Level 4

write mechanisms for nucleophilic substitution reactions, with acid or base catalysis

Synthetic Skills - Level 5

create a synthetic sequence to prepare a given target molecule