Grade 12

Grade 12Nitrogen-containing organic compounds


Preparation and properties of amines


Introduction

Amines are important organic compounds that contain nitrogen. They are derived from ammonia (NH 3) and are characterized by the presence of a nitrogen atom bonded to one or more alkyl or aryl groups. Amines play important roles in both organic and biological chemistry and are found in many biological molecules such as amino acids, proteins, hormones, and vitamins.

Structure of amines

Amines can be classified based on the number of carbon-containing groups attached to the nitrogen atom:

  • Primary amine: One carbon group attached to nitrogen. Example: methylamine (CH 3 NH 2).
  • Secondary amines: Two carbon groups attached to a nitrogen. Example: dimethylamine ((CH 3) 2 NH).
  • Tertiary amine: Three carbon groups attached to a nitrogen. Example: trimethylamine ((CH 3) 3 N).

Preparation of amines

1. Reduction of nitro compounds

A common method for preparing amines is the reduction of nitro compounds. Nitro compounds, which contain -NO 2 group, are reduced to amines using various reducing agents:

R-NO 2 + 6[H] → R-NH 2 + 2H 2 O

Common reducing agents include:

  • Hydrogen gas (H 2) with a metal catalyst such as palladium, platinum or nickel.
  • Iron powder and hydrochloric acid.
  • Tin and hydrochloric acid.

2. Reduction of amides

Amides can be reduced to amines using a strong reducing agent such as lithium aluminium hydride (LiAlH 4).

RCONH2 + 4[H]  R- CH2NH2 + H2O

3. Gabriel phthalimide synthesis

The Gabriel phthalimide synthesis is used to prepare primary amines. In this method, potassium phthalimide is reacted with an alkyl halide to form an N-alkyl phthalimide. Hydrolysis of the alkylated intermediate yields the primary amine.

O=C , C 8 H 4 O 3 N - K + + RX → C 8 H 4 O 2 NR → RNH 2

4. From alkyl halides

Amines can also be prepared by reacting an alkyl halide with ammonia, undergoing a nucleophilic substitution reaction.

RX + NH3 → R- NH2 + HX

Properties of amines

Physical properties

Boiling point: Amines generally have higher boiling points than hydrocarbons because they have less hydrogen bonding, but lower than alcohols because they have less hydrogen bonding. For example, ethylamine has a higher boiling point than ethane but lower than ethanol.

Solubility: Lower aliphatic amines are soluble in water due to their ability to form hydrogen bonds. However, solubility decreases with increase in molecular size due to the hydrophobic nature of the alkyl group.

Chemical properties

Amines have a diverse chemical behaviour and participate in many reactions, which are described below.

1. Originality

Amines are basic due to the presence of a lone pair of electrons on the nitrogen atom, which can accept a proton. This characteristic leads them to act as Lewis bases. An example of this is reacting with acids to form ammonium salts.

RNH 2 + HCl → RNH 3 Cl

2. Alkylation

Amines react with alkyl halides in a series of nucleophilic substitution reactions, resulting in the formation of secondary and tertiary amines and quaternary ammonium salts.

RNH2 + R'X → RR'NH + HX

3. Acylation

Amines undergo acylation reactions with acyl chlorides or anhydrides to form amides. This is a nucleophilic acyl substitution reaction.

RNH2 + R'COCl → RNHCO-R' + HCl

4. Reaction with nitrous acid

Primary aliphatic amines react with nitrous acid to form alcohols and evolve nitrogen gas.

RNH2 + HONO → ROH + N2 + H2O

Aromatic amines such as aniline react with nitrous acid to form diazonium salts.

C 6 H 5 NH 2 + HONO + HCl → C 6 H 5 N 2 Cl + 2H 2 O

5. Formation of Schiff base

Amines react with aldehydes or ketones to form imines, also known as Schiff bases. This condensation reaction occurs mainly with primary amines.

RNH2 + R'CHO → RN=CHR' + H2O

Visual representation of amines

Primary amine R- NH2 Secondary amine (R) 2 -NH

Applications of amines

Amines are used in the synthesis of many pharmaceuticals and dyes. Additionally, they are used in the manufacture of polymers and as intermediates in the production of agricultural chemicals and surfactants.

Conclusion

Understanding the preparation and properties of amines is important because they have wide applications in various fields including pharmaceuticals and chemical synthesis. The structural features and chemical reactivity of amines continue to fascinate chemists, enabling the synthesis of new compounds to meet industrial demands.


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