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ammonium compounds. E.g: NH4+Clammonium chloride (CH3)4N+Cltetramethylammonium chloride Amines have higher boiling points than hydrocarbon with similar Mr intermolecular hydrogen bonding.
with water molecules Solubility in water decreases with increasing num. of C atoms.
Naming amines
Use the suffix ylamine after a stem indicating the
Exercise : Name the following compounds. 1. (CH3CH2)2NH 2. (CH3)3N Write the structural formulas of the following compounds: a) Propylamine b) 2-nitrophenylamine
Formation of amines
1)
Nitrile reduction Reagent and condition : LiAlH4 in dry ether or mixture of Na and ethanol or H2, Ni, 140C. Product : alkyl amine
Eg. :
RCN
RCH2NH2
2) Reduction of nitrobenzene
Reagent & condition : reflux with tin and excess conc.
The metal and acid gives off H2(g) which performs the
Basicity of amines
Amines are weak base. Due to ability of lone pair in the nitrogen atom to accept a
Order of base strength : ethylamine > ammonia > phenylamine Base strength pKb : 3.3 4.8 9.4 decrease * The lower the pKb value, the stronger the base.
electron density on the N atom more available to accept proton than ammonia. The ethyl group pushes electron onto the NH3+ group on the conjugate acid stabilises the ion.
ammonia.
electrons on the nitrogen atom over the benzene ring hence less available to accept a proton.
amines. E.g : propylamine is more basic than ammonia. The R-group increases electron density on N atom, making it more available to accept a proton.
basicity of amines. E.g 3-chlorophenylamine is weaker then phenylamine. Electron-withdrawing Cl atom makes the lone pair in N atom less available to accept proton.
Reactions of Phenylamine
1.
Reaction with HNO2 Reagent : NaNO2 and conc. HCl Condition : <5C Product : diazonium salt
The aromatic diazonium ion formed is more stable due to delocalisation of electrons to the benzene ring.
will
salt in this reaction. This is because the diazonium group, -N+ N, is unstable. It decompose quickly to give N2(g), alcohol and alkene.
The benzenediazonium ion reacts with nucleophiles
electrophile. It can attack the benzene ring, especially those that have EDG such as OH group attached to it. Reagent : diazonium salt and phenol Condition : Cold alkaline solutions Product : bright orange precipitate of (4-hydroxyphenyl) azobenzene. E.g
due to the extensive delocalisation of electrons via the N=N bond. Because it is very stable, the dyes do not fade. This coupling reaction is used in formation of dyestuff. Other aromatic amines and arenes can be used to make dyes.
Reactions of phenylamine.
Reaction with Aqueous Bromine (electrophilic substitution) Aliphatic amines have no reaction with aqueous bromine. Condition : room temperature. Observation : reddish-brown bromine solution decolourised, white ppt of 2,4,6-tribromophenylamine formed and steamy white fumes of HBr liberated.