Reactions of amides
Page 1: Hydrolysis of Amides
Overview of Hydrolysis
Hydrolysis is the reverse reaction of amidation, utilized for splitting an amide using water and an acid or a base.
Page 2: Acid Hydrolysis of Amides
Process
Amides are subjected to acid hydrolysis in the presence of heat.
Products
The result of this reaction is the formation of:
A carboxylic acid
An ammonium salt
Page 3: Base Hydrolysis of Amides
Process
Amides undergo base hydrolysis with heat as well.
Products
The products obtained from this reaction include:
A carboxylate salt
An amine or ammonia
Page 4: Example of Base Hydrolysis
Analyzing N-methylpentanamide
Given: N-methylpentanamide with NaOH.
Need: To determine the products of base hydrolysis.
Connect: This involves identifying the carboxylate salt and amine produced.
Problem Structure
The breakdown of the amide bond occurs between the carboxyl carbon atom and the nitrogen atom.
Page 5: Detailed Hydrolysis of N-methylpentanamide
Products
The products of hydrolysis include:
Carboxylate salt
Amine
Important Notes
In the base hydrolysis of the amide, the amide bond is cleaved.
Page 6: Learning Check
Exercise
Task: Draw the condensed structural formulas for the products from the hydrolysis of the specified amide using HCl.
Page 7: Solution Exercise
Drawing Structural Formulas
Again, draw the condensed structural formulas for the products received from hydrolysis of the given amide with HCl.
Page 8: Concept Map on Amines and Amides
Characteristics of Amines and Amides
Both amines and amides contain a nitrogen atom bonded to alkyl or aromatic groups.
Amines can be heterocyclic and soluble in water when they have up to 6 carbon atoms.
Reactivity
They react with water as weak bases and can also react with acids.
Carboxylic acids interact with amines to form amides.
Hydrolysis Outcomes
Acid hydrolysis yields:
Carboxylic acids
Ammonium salts
Base hydrolysis yields:
Carboxylate salts
Amines