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Organic
Chemistry III
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Professor
Carl C. Wamser
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Chapter
20 Skills
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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
