Reactions of Carboxylic Acids and Derivatives
(Carey, Chap. 19 & 20)

Reaction Product Notes
 
carboxylate anions;
water soluble; soaps;
HCO3- diagnostic for carbox.
acid (---> CO2 gas)
 
 
Fischer esterification,
   equilibrium, K = 1.
Ester hydrolysis,
   (HO- cat.= saponification)
 
diazomethane;
prep. of methyl esters
 
reduction of acid or ester
   to 1o alcohol
 
 
 
5 or 6 membered ring
cyclic anhydride
 
 
 
5 or 6 membered ring
lactone
 
 
prep. of anhydrides
 
 
prep. of ketones

 
 
prep. of aldehydes
 
 
prep. of esters
 
 
prep. of amides
 
 
transesterification
 
 
aminolysis of esters
 
 
double addition of Grignard
 
hydrolysis of amides;
very slow reaction
 
 
prep. of amines
 
hydrolysis of nitriles;
very slow reaction
 
prep. of 1o amines
 
single addition of Grignard;
prep. of ketones
 
alpha halogenation of
   carboxylic acids
 
Hofmann rearrangement;
prep. of 1o amines

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