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Amines - Structure and Classification

Grade 12CBSEChemistry

Review the key concepts, formulae, and examples before starting your quiz.

🔑Concepts

Amines are regarded as derivatives of ammonia (NH3NH_3), formed by the replacement of one, two, or all three hydrogen atoms by alkyl and/or aryl groups.

Structure of Amines: The nitrogen atom in amines is sp3sp^3 hybridized. Due to the presence of a lone pair of electrons, the geometry is trigonal pyramidal. The CNEC-N-E (where EE is HH or CC) bond angle is slightly less than the tetrahedral angle of 109.5109.5^\circ; for example, it is 108108^\circ in trimethylamine.

Classification: Amines are classified as primary (11^\circ), secondary (22^\circ), and tertiary (33^\circ) depending upon the number of hydrogen atoms replaced by alkyl or aryl groups in the ammonia molecule.

Primary (11^\circ) amines: Only one hydrogen atom of NH3NH_3 is replaced by an alkyl/aryl group, resulting in the functional group NH2-NH_2 (amino group).

Secondary (22^\circ) amines: Two hydrogen atoms of NH3NH_3 are replaced, resulting in the functional group >NH>NH (imino group).

Tertiary (33^\circ) amines: All three hydrogen atoms of NH3NH_3 are replaced, resulting in a tertiary nitrogen atom >N>N-.

Aryl Amines: In these amines, the NH2-NH_2 group is directly attached to the benzene ring. The simplest example is Aniline (C6H5NH2C_6H_5NH_2).

📐Formulae

RNH2 (Primary Amine)R-NH_2 \text{ (Primary Amine)}

R2NH (Secondary Amine)R_2NH \text{ (Secondary Amine)}

R3N (Tertiary Amine)R_3N \text{ (Tertiary Amine)}

CnH2n+1NH2 (General formula for Aliphatic Primary Amines)C_nH_{2n+1}NH_2 \text{ (General formula for Aliphatic Primary Amines)}

[R4N]+X (Quaternary Ammonium Salt)[R_4N]^+X^- \text{ (Quaternary Ammonium Salt)}

💡Examples

Problem 1:

Classify the following amine as primary, secondary, or tertiary: (CH3)3CNH2(CH_3)_3CNH_2.

Solution:

It is a Primary (11^\circ) amine.

Explanation:

Even though the carbon atom attached to the nitrogen is a tertiary carbon (t-butyl group), the nitrogen atom itself is attached to only one carbon atom and has two hydrogen atoms (NH2-NH_2 group). Therefore, it is a primary amine.

Problem 2:

Give the IUPAC name and classification for CH3CH2NHCH3CH_3CH_2NHCH_3.

Solution:

IUPAC Name: NN-Methylethanamine. Classification: Secondary (22^\circ) amine.

Explanation:

The nitrogen is attached to two alkyl groups (ethyl and methyl), making it a secondary amine. For naming, the larger alkyl group (ethane) is treated as the parent chain.

Problem 3:

Why is the bond angle in (CH3)3N(CH_3)_3N (108108^\circ) less than the ideal tetrahedral angle (109.5109.5^\circ)?

Solution:

Due to lone pair-bond pair repulsion.

Explanation:

In sp3sp^3 hybridized nitrogen, the lone pair occupies one of the hybrid orbitals. According to VSEPR theory, lone pair-bond pair repulsions are stronger than bond pair-bond pair repulsions, which pushes the CNCC-N-C bonds closer together, decreasing the angle.

Structure and Classification - Revision Notes & Key Formulas | CBSE Class 12 Chemistry