Key Terms

  • carboxyl group
  • carboxylation
  • carboxylic acid, RCO2H
  • nitrile
  • acid anhydride
  • acid halide
  • acyl phosphate
  • amide
  • carboxylic acid derivative
  • chain-growth polymer
  • ester
  • Fischer esterification reaction
  • lactam
  • lactone
  • nucleophilic acyl substitution reaction
  • saponification
  • step-growth polymer
  • thioester

Summary of Reactions

Preparation of carboxylic acids (Section 11.4)

  • Oxidation of alkylbenzenes

Chemical reaction showing the oxidation of p-nitrotoluene into p-nitrobenzoic acid using potassium permanganate and water at 95 degrees Celsius.

 

 

  • Hydrolysis of nitriles

Nitrile reacts with hydronium or sodium hydroxide and water to produce carboxylic acid. Nitrile carbon becomes the carboxyl.

Reactions of carboxylic acids (Section 11.6)

  • Conversion into acid chlorides

Conversion of a carboxylic acid to an acid chloride, by reaction with thionyl chloride in trichloromethane (chloroform). The hydroxyl group is replaced by a chlorine atom.

  • Conversion into esters

At the top, reaction of a carboxylate ion with an alkyl halide to give an ester through an S N 2 mechanism. At the bottom, reaction of a carboxylic acid with an alcohol to yield an ester.

  • Conversion into amides

Conversion of a carboxylic acid to an N-substituted amide by reaction with a monosubstituted amine and D C C.

  • Reduction to yield primary alcohols

Conversion of a carboxylic acid to a primary alcohol using lithium aluminum hydride.

Reactions of acid chlorides (Section 11.7)

  • Hydrolysis to yield acids

Hydrolysis of an acid chloride using water to give a carboxylic acid and hydrochloric acid.

  • Reaction with carboxylates to yield anhydrides

Reaction of an acid chloride with a carboxylate in to form an acid anhydride.

  • Alcoholysis to yield esters

The reaction of an acid chloride with an alcohol in the presence of pyridine to form an ester.

  • Aminolysis to yield amides

Two molecules of ammonia react with an acid chloride to form an amide and ammonium chloride.

  • Reduction to yield primary alcohols

Reaction of an acid chloride with lithium aluminum hydride in ether followed by treatment with acid to generate an alcohol.

  • Grignard reaction to yield tertiary alcohols

Reaction of an acid chloride with two moles of Grignard reagent in ether followed by treatment with acid to give a tertiary alcohol.

Reactions of acid anhydrides (Section 11.8)

  • Hydrolysis to yield acids

Reaction of an acid anhydride with water gives two equivalents of carboxylic acid.

  • Alcoholysis to yield esters

The reaction of an acid anhydride with an alcohol forms an ester and a carboxylic acid.

  • Aminolysis to yield amides

The reaction of an acid anhydride with two equivalents of ammonia gives an amide and an ammonium carboxylate salt.

Reactions of esters (Section 11.9)

  • Hydrolysis to yield acids

An ester is hydrolyzed to a carboxylic acid and alcohol using either acid or base.

  • Reduction to yield primary alcohols

An ester is reduced to an alcohol using lithium aluminum hydride in ether followed by treatment with acid.

 

 

  • Grignard reaction to yield tertiary alcohols

The reaction of an ester with a Grignard reagent in ether followed by treatment with acid produces an alcohol

Reactions of amides (Section 11.10)

  • Hydrolysis to yield acids

Hydrolysis of an amide to a carboxylic acid using acid or base.

  • Reduction to yield amines

Reduction of amides to amines using lithium aluminum hydride in ether followed by treatment with acid.

Preparation of nitriles (Section 11.11)

  • SN2 reaction of alkyl halides

Alkyl bromide reacts with sodium cyanide to produce a nitrile. Cyanide carbon becomes nitrile carbon.

Reactions of nitriles (Section 11.11)

  • Hydrolysis to yield carboxylic acids

Nitrile reacts first with sodium hydroxide and water, then with hydronium to produce carboxylic acid and ammonia. Nitrile nitrogen becomes ammonia nitrogen.

  • Reduction to yield primary amines

Nitrile reacts first with lithium aluminum hydride, then with water to produce a primary amine. Nitrile nitrogen becomes amine nitrogen.

  • Reaction with Grignard reagents to yield ketones

Nitrile reacts first with organomagnesium bromide in ether, then with hydronium to produce a ketone and ammonia.

License

Icon for the Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License

Fundamentals of Organic Chemistry Copyright © by Kirsten Kramer and Cassandra Lilly is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.

Share This Book