Nitrogen containing organic compounds
Unit 10 - NOTE GUIDE
• Amides
• Amines
• Aniline
• Diazonium salts
Amines
Structure & properties of alcohols
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• Small amines of all types are soluble in water because of the formation of hydrogen bonds with water.
• Amines have higher boiling points compared to alkanes with similar molecular masses due to the
formation of hydrogen bonds and dipole–dipole interactions in addition to London dispersion forces.
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Reactions of amines
1) With alkyl halides
• The reaction between a primary amine and alkyl halides gives a mixture of products. This is a
nucleophilic susbtitution reaction
2) With carbonyl compounds
3) With acid chlorides
4) With nitrous acid (NaNO2 + HCl)
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• Aromatic diazonium salts are more stable than alkyl diazonium salts. Therefore, solutions of
aromatic diazonium salts can be obtained at low temperatures (0 – 5°C)
Aniline
Structure of aniline
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Reactions of aniline
1) Reaction with Br2
• Similar to phenol, aniline readily reacts with bromine to give 2,4,6-tribromoaniline, as the NH2
group highly activates the benzene ring towards electrophilic substitution
2) Formation of diazonium salt
• Since aromatic diazonium salts are more stable than aliphatic diazonium salts, they can be isolated
when the reaction is carried out at low temperatures (0 – 5°C)
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Diazonium salts
Reactions of Diazonium salts
1) Reactions that replace diazonium group
2) Coupling reactions
• Diazonium ions can act as electrophiles because they contain a positive charge on nitrogen
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Basicity of nitrogen containing compounds
• Aliphatic amine are more basic than aniline
Reason – In aniline, the lone pair of electrons on nitrogen is delocalized onto the benzene ring,
reducing the availability of the lone pair on nitrogen
• Amides are less basic than aniline
Reason – In amides, unlike in aniline, the lone pair on nitrogen is delocalized through the carbonyl
(C=O) group. Although amides form only two resonance structures, the electron loss felt by nitrogen
in amides is greater because oxygen is a highly electronegative atom.
• Basic strength order
Conversions
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