Acyl Substitution
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Table of Carboxylic Acid Derivatives and Acyl Substitution
Diagonal Compound (Turquoise) + Off-Diagonal Reagent = New Diagonal Compound, Read Clockwise
For example:  A Carboxylic Acid + Thionyl Chloride = An Acid or Acyl Halide and Anhydride + Alcohol = An Ester

Carboxylic Acid

alkanoic acid

 Base Amine, Heat

or

Amine, DCC

   Alcohol, Acid Catalyst
(Fischer Esterification)

or

Diazomethane

or

Electrophilic Addition

 Acid Catalyst, Heat Thionyl Chloride, Pyridine Catalysis

or

Phosphorous Tribromide
Acid Carboxylate Salt

alkanoate

 Ammonium, Heat        
Acid, Water Base Amide

Primary, amide
Secondary, N-alkylamide
Tertiary, N,N-dialkylamide

 Thionyl Chloride, heat      
Acid, Water Base Base Nitrile

alkanenitrile

      
Acid, Water Base (Saponification) Amine   Ester

alkyl alkanoate

    
Water Base Amine   Alcohol

or

Alkoxide

 Anhydride

alkanoic anhydride

  
Water Base Amine   Alcohol

or

Alkoxide

 Carboxylic Acid

or

Carboxylate Salt

 Acid or Acyl Halide

alkanoyl halide

 

 

 

 

 

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Wednesday, February 01, 2012 09:03