Official JEE Chemistry Revision Material: JEE Chemistry Amines Notes Set 05
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Aniline: Preparation and Physical Properties
1. Laboratory method: \(\ce{C6H5NO2 + 6[H] ->[Sn / HCl] C6H5NH2 + 2H2O}\). Industrially iron and HCl are used.
2. From phenol: heating with ammonia and anhydrous zinc chloride at about 300°C.
3. From benzamide by Hofmann bromamide reaction, from benzoic acid by Schmidt reaction, from phenylmagnesium bromide with chloramine, or by hydrolysis of phenyl isocyanide.
4. Fresh aniline is a colourless oily liquid that darkens in air and light. It is toxic, steam volatile, denser than water and boils at about 184°C. It is purified by steam distillation.
Reactions of Aniline
| Reaction | Result |
|---|---|
| Basic nature | Weak base; gives anilinium salts with acids. Lone pair is delocalised into the ring, so it is weaker than aliphatic amines. |
| Alkylation | Mono, di and tri-methylation gives N-methylaniline, N,N-dimethylaniline and finally the quaternary salt. |
| Acylation | With acetyl chloride or anhydride gives acetanilide; with benzoyl chloride and NaOH gives benzanilide (Schotten-Baumann reaction). |
| Carbylamine reaction | Gives phenyl isocyanide with a foul smell. |
| Bromine water | White precipitate of 2,4,6-tribromoaniline immediately. |
| Direct nitration | Mixture of o-, m- and p-nitroaniline plus oxidation products, because of anilinium ion formation. |
| Protected nitration | Acetylate first, nitrate, then hydrolyse to get mainly p-nitroaniline. |
| Sulphonation | Heating anilinium hydrogen sulphate at about 200°C gives sulphanilic acid (para). |
| Friedel-Crafts | Fails because the amine forms a complex with AlCl3. |
| Schiff's base | With benzaldehyde gives benzylideneaniline. |
| Diazotisation | \(\ce{C6H5NH2 + NaNO2 + 2HCl ->[0-5 °C] C6H5N2+Cl- + NaCl + 2H2O}\) |
Benzenediazonium Chloride
It is prepared at 0 to 5°C because on warming it reacts with water to give phenol. The aryl diazonium ion is stabilised by delocalisation with the ring, while alkyl diazonium salts decompose at once.
| Reagent | Product | Type |
|---|---|---|
| \(\ce{CuCl / HCl}\) or \(\ce{CuBr / HBr}\) or \(\ce{CuCN / KCN}\) | chlorobenzene, bromobenzene, benzonitrile | Sandmeyer |
| Cu powder with HCl or HBr | chlorobenzene or bromobenzene | Gattermann |
| KI | iodobenzene (no catalyst needed) | replacement by iodine |
| \(\ce{HBF4}\), then heat | fluorobenzene | Balz-Schiemann |
| \(\ce{NaNO2}\) with Cu, heat on the fluoroborate | nitrobenzene | replacement by nitro |
| Water, warm | phenol | hydrolysis |
| \(\ce{H3PO2}\) or ethanol | benzene | reduction (removal of the diazo group) |
| Phenol in alkali or aromatic amine in weakly acidic medium | azo dye (p-hydroxyazobenzene, p-aminoazobenzene) | coupling at para position |
| Alkaline beta-naphthol | orange-red dye | test for primary aromatic amines |
Nitrobenzene
1. Made by nitration of benzene with conc. nitric and conc. sulphuric acids at 50 to 60°C. It is a pale yellow, steam volatile liquid with an almond-like smell and boils at 211°C. It is poisonous.
2. The nitro group deactivates the ring and directs meta. Nitration with fuming nitric acid and sulphuric acid gives m-dinitrobenzene, sulphonation gives m-nitrobenzenesulphonic acid, and chlorination with Cl2/AlCl3 gives m-chloronitrobenzene.
3. It does not undergo Friedel-Crafts reaction and is used as a solvent for it.
4. Reduction depends on the medium: Sn/HCl, Fe/HCl or H2/Pd give aniline; Zn/NH4Cl gives N-phenylhydroxylamine; electrolytic reduction in strongly acidic medium gives p-aminophenol; alkaline media give azoxybenzene, azobenzene and hydrazobenzene in turn.
5. Mullikan-Barker test: Zn/NH4Cl converts nitrobenzene to phenylhydroxylamine, which gives a silver mirror with Tollens' reagent.
Nitriles and Isocyanides
1. Alkyl halide with KCN gives the nitrile RCN, whereas with AgCN it gives the isocyanide RNC. Aryl halides do not react with KCN; aryl cyanides come from diazonium salts.
2. Nitrile: hydrolysis gives acid; reduction gives primary amine; Grignard reagent gives ketone. Isocyanide: hydrolysis gives primary amine and formic acid; reduction gives secondary amine (N-methyl).
3. Methyl isocyanate was the gas released in the Bhopal gas tragedy.
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