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Amide is an organic compound. It is also known as an organic amide or carboxamide. It contains a carbonyl functional group that is bonded with a nitrogen atom. The simplest amide is a derivative of ammonia NH3, here one hydrogen atom is replaced by an acyl group. In this article, we will define Amide, its types, structures, along with its properties.
Table of Content What is Amide?Amide, also known as an organic amide or carboxamide, is a compound with the general formula R−C(=O)−NR′R″. Here R, R’, and R″ represent a hydrogen atom or an organic group. Amides are derived from carboxylic acids, which contain the -COOH group. In an amide, the -OH part of that group is replaced by an -NH2 group. Amides are essential in organic chemistry. They have various subclasses, such as carboxamides and phosphoramides. Amide Definition
Amide Functional GroupAmide functional group is a compound with a carbonyl group attached to an amine group which are derived from the distinct functional group like carboxylic acid. It is represented as
Read More, Functional Group Amides ExamplesSome examples of amides include:
Amide FormulaThe formula for an amide is illustrated as:
This formula refers explicitly to primary amides. The nitrogen atom is bonded to two hydrogen atoms and no other R group. Amide StructureAmide group is a functional group that consists of a carbonyl group (C=O) linked to a nitrogen atom (N). The lone pair of electrons on the nitrogen atom is delocalized into the carbonyl group. This forms a partial double bond between nitrogen and carbon.
The O, C, and N atoms have molecular orbitals. They are occupied by delocalized electrons, creating a conjugated system. Consequently, the three nitrogen bonds in amides are planar, unlike the pyramidal shape of amines. Amides can participate in hydrogen bonding with water and other protic solvents. They can act as both hydrogen bond acceptors and donors. Classifications of AmidesAmides can be classified into three types. This is based on the position of the nitrogen atom linked to the carbon atom. The three types of amides are:
Primary AmidesIn Primary Amides, the nitrogen atom is attached to a single carbon atom. The general formula for a primary amide is RCONH2, where R represents an organic group or a hydrogen atom. Primary amides are named by changing the name of the acid by removing “-oic acid” or “-ic acid” and after that adding “-amide”. For Example: Methanamide, Ethanamide, Propanamide, and Acetoamide. Secondary AmidesIn Secondary Amides(or 2° amides), the nitrogen atom is attached to two carbon atoms. The general formula for a secondary amide is RCONHR’, where R and R’ represent organic groups or a hydrogen atom. Secondary amides are named using an uppercase N to designate that the alkyl group is on the nitrogen atom. Alkyl groups attached to the nitrogen are called substituents. Tertiary AmidesIn Tertiary Amides(or 3° amides), the nitrogen atom is attached to three carbon atoms. The general formula for a tertiary amide is RCONR’R″, where R ,R’ and R” represent organic groups or hydrogen atoms. Tertiary amides are named similarly as secondary amides, but with two N’s.
Amide BondAmide bond is a specific type of covalent chemical bond. In organic chemistry, it is formed by the condensation reaction between a carboxylic acid and an amine. When the amide group occurs in the main chain of a protein, it’s called a peptide bond. An isopeptide bond occurs in a side chain. Peptide bonds are essential in forming proteins. They link amino acids in a specific sequence. Synthesis of AmideThere are several methods for the synthesis of amides. One common method is the direct reaction of a carboxylic acid and an amine using a coupling agent such as DCC. The reaction can be represented as follows:
Another method involves the reaction of an acidic chloride with ammonia. It also involves the reaction with a primary amine or a secondary amine. The reaction can be represented as follows:
Amide HydrolysisAmide hydrolysis is the breakdown of an amide bond in a compound. It typically happens through a reaction with water. This process can occur under both acidic and basic conditions. Amide hydrolysis is essential in various applications. It is used to hydrolyse peptides and proteins. The products of amide hydrolysis can be used to synthesize amines and carboxylic acids. Reduction of AmideAmides can be reduced to amines using various methods. One standard way is using a strong reducing agent like lithium aluminum hydride (LiAlH4). This reaction involves adding a hydride to the amide carbonyl. Then, it eliminates and adds a hydride ion to give the amine.
LiAlH4 is a strong reducing agent. It reacts violently with water. So, the reaction is carried out in dry solvents such as anhydrous ether. Amide Vs. AmineThe difference between Amides and Amines are as follows:
Applications of AmidesSome applications of amides include:
Read More, Amides – Solved ExamplesExample 1: Which compound has the higher boiling point—pentanamide (CH3CH2CH2CH2CONH2) or propyl acetate (CH3COOCH2CH2CH3)? Explain. Solution:
Example 2: What are the products of the hydrolysis of an amide? Solution:
Amides – Frequently Asked QuestionsWhat is Amide Formula?
What are Characteristics of Amides?
What are the Types of Amides?
Is NH3 called Amide?
What is 3o Amide?
Is Amide Acidic or Basic?
Is Amide Saturated or Unsaturated?
Explain Amide Solubility in Water?
What is the pKa of Amide?
Is an Amide an Amine?
Are Amides Nucleophiles?
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