What is an Amide?
An amide is a functional group consisting of a single bond between a carbonyl group and a nitrogen atom.
Amide is sometimes referred to as a derivative of carboxylic acids in which the OH group of COOH is replaced by NH2, NHR, or NR2 of an amine.
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What is Hydrolysis?
Hydrolysis is a chemical reaction that occurs when compounds interact with water, resulting in the disintegration of both the material and the water.
Hydrolysis of Amide
Even after extended heating, amide does not interact with water molecules to disintegrate. However, amide hydrolysis is not impossible. It interacts with water molecules in both acidic and basic environments.
In an acidic environment, amide reacts with water to produce a carboxylic acid and the salt of ammonia or amine.
In a basic environment, amide reacts with the water molecule to produce a carboxylic acid and ammonium or amine salt.
- Enzymes catalyze amide hydrolysis in the human body.
Types of Amide Hydrolysis
Amide can bind with a water molecule in two distinct ways, namely hydrogen bonding and ionic bonding.
- Acid Catalysed Amide Hydrolysis
- Base Catalysed Amide Hydrolysis
Acid Catalysed Amide Hydrolysis
In an acidic environment, amide reacts with water to produce a carboxylic acid and the salt of ammonia or amine.
Mechanism:
Step 1: Protonation of amide carbonyl
Since we only have a weak nucleophile and a poor electrophile, we will activate the amide.
Protonation of the carbonyl group of the amide makes it more electrophilic.
Step 2: Nucleophilic Addition
The lone oxygen pairs would attack the carbonyl group, and the electron would travel toward the oxonium ion to produce a tetrahedral intermediate.
Step 3: Proton transfer
An oxygen proton is lost to neutralize the charge.
Step 4: Proton transfer
Proton assaults the group of -NHR so that it may leave without difficulty.
Step 5: Elimination of R’-NH2
Oxygen lone pairs assault the carbon atom to displace the R’-NH2 group.
Step 6: Deprotonation of oxonium ion
An oxygen proton is lost to neutralize the charge.
Base Catalysed Amide Hydrolysis
In a basic environment, amide reacts with the water molecule to produce a carboxylic acid and ammonium or amine salt.
Mechanism:
- In base-catalyzed amide hydrolysis, the amide is heated with aqueous NaOH or KOH at boiling temperature.
- The nucleophilic hydroxide ion forms a tetrahedral intermediate by combining with the carbonyl carbon.
- NR2 is attacked by Proton.
- The ion of oxonium attacks the carbon atom.
- HNR2 is divided.
Frequently Asked Questions on Amide Hydrolysis
Q.1 What are amides?
A single bond connects the carbonyl group to the nitrogen atom in an amide functional group.
Amide is sometimes referred to as derivatives of carboxylic acids in which the OH group of COOH is replaced by NH2, NHR, or NR2 of an amine.
Q.2 What is acid catalysed amide hydrolysis?
The amide reacts with water in an acidic environment.
In an acidic environment, amide reacts with water to produce a carboxylic acid and the salt of ammonia or amine.
Q.3 What is base catalysed amide hydrolysis?
The amide reacts with water in a basic environment. In a basic environment, amide reacts with the water molecule to produce a carboxylic acid and ammonium or amine salt.
Q.4 Is amide hydrolysis feasible?
Yes, amide hydrolysis is a viable process. It interacts with water molecules in both acidic and basic environments.
In an acidic environment, amide reacts with water to produce a carboxylic acid and the salt of ammonia or amine.
In a basic environment, amide reacts with the water molecule to produce a carboxylic acid and ammonium or amine salt.
