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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Thursday, April 06, 2017 13:18