Amines
Class 12 Chemistry · Chemistry Part II · Chapter 4
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Summary
Amines are derivatives of ammonia in which one, two or three hydrogen atoms are replaced by alkyl or aryl groups, giving primary, secondary and tertiary amines respectively. The nitrogen is \(sp^3\) hybridised and pyramidal with an unshared electron pair, which makes amines behave as Lewis bases and nucleophiles. They are named by common (alkylamine) and IUPAC (alkanamine) systems. Amines are prepared by reduction of nitro compounds, nitriles and amides, by ammonolysis of alkyl halides, by the Gabriel phthalimide synthesis (for primary amines) and by the Hoffmann bromamide degradation. Primary and secondary amines form intermolecular hydrogen bonds, raising their boiling points. The basic strength of amines depends on the interplay of the inductive effect, solvation and steric hindrance; aliphatic amines are stronger bases than ammonia while aromatic amines like aniline are weaker because the nitrogen lone pair is delocalised into the ring. Amines undergo alkylation, acylation, the carbylamine test (for primary amines), reaction with nitrous acid and electrophilic substitution. Aromatic primary amines react with nitrous acid at low temperature to give diazonium salts, which are valuable intermediates: their diazo group can be replaced by halides, cyanide, hydroxyl and other groups, or retained in coupling reactions that yield azo dyes.
Structure, classification and nomenclatureMethods of preparation of aminesPhysical properties and hydrogen bondingBasic strength of aminesChemical reactions and testsDiazonium salts and their reactions
Key terms
Amine
A derivative of ammonia in which H atoms are replaced by alkyl or aryl groups; a Lewis base.
Gabriel phthalimide synthesis
A method that gives pure primary aliphatic amines from phthalimide and an alkyl halide.
Hoffmann bromamide degradation
Conversion of an amide to a primary amine with one fewer carbon using bromine and alkali.
Diazonium salt
An aryl compound of the form ArN2+ X-, a key intermediate in aromatic synthesis.
Carbylamine reaction
A test in which primary amines give foul-smelling isocyanides with chloroform and alcoholic KOH.
Coupling reaction
Reaction of a diazonium salt with phenol or arylamine to form a coloured azo dye.
Extra questions & answers
Try one from this chapter
Amines are derivatives of ammonia in which H atoms are replaced by: