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Reactions of Benzenediazonium Chloride
Benzenediazonium chloride, \( \ce{C6H5N2+Cl-} \), is a colourless crystalline solid that is soluble in water and stable only in the cold (0–5 °C). It is the starting point for many aromatic compounds because the \( \ce{N2} \) group leaves easily as nitrogen gas.
| Reagent | Product | Name of reaction |
|---|---|---|
| \( \ce{Cu2Cl2/HCl} \) | Chlorobenzene | Sandmeyer |
| \( \ce{Cu2Br2/HBr} \) | Bromobenzene | Sandmeyer |
| \( \ce{Cu2(CN)2/KCN} \) | Benzonitrile | Sandmeyer |
| \( \ce{Cu/HCl} \) or \( \ce{Cu/HBr} \) | Chlorobenzene or bromobenzene | Gattermann |
| \( \ce{HBF4} \), then heat | Fluorobenzene | Balz–Schiemann |
| \( \ce{HBF4} \), then \( \ce{Cu/NaNO2} \), heat | Nitrobenzene | |
| \( \ce{KI} \) | Iodobenzene | Direct replacement, no catalyst |
| \( \ce{H2O} \), warm, or dilute \( \ce{H2SO4} \) | Phenol | Hydrolysis |
| \( \ce{H3PO2} \) or \( \ce{C2H5OH} \) | Benzene | Reduction (removal of the amino group) |
| \( \ce{SnCl2/HCl} \) | Phenylhydrazine | Reduction |
Coupling Reactions
The diazonium ion is a weak electrophile and attacks strongly activated rings, usually at the para position, to give coloured azo compounds containing the –N=N– link. The pH of the medium matters.
| Coupling partner | Medium | Product and colour |
|---|---|---|
| Phenol | Weakly alkaline (pH 8–10) | p-Hydroxyazobenzene, orange |
| Aniline | Weakly acidic (pH 3–5) | p-Aminoazobenzene, yellow |
| N,N-Dimethylaniline | Weakly acidic (pH 3–5) | p-Dimethylaminoazobenzene, yellow |
| 2-Naphthol | Weakly alkaline (pH 8–10) | 1-(Phenylazo)-2-naphthol, red |
Nitroalkanes
Nitroalkanes can be made by heating an alkyl halide with silver nitrite, or by nitrating alkanes in the vapour phase (\( \ce{HNO3} \), about 600 °C, which also breaks C–C bonds). Nitroacetic acid loses \( \ce{CO2} \) on heating to give nitromethane. They are colourless liquids with a sweet smell.
| Reagent | Product |
|---|---|
| \( \ce{Sn/HCl} \), \( \ce{H2/Pd} \), \( \ce{Na/C2H5OH} \) or \( \ce{LiAlH4} \) | Primary amine, \( \ce{RNH2} \) |
| Tautomerism | aci-nitro form, \( \ce{CH3CH=N(O)OH} \) |
| \( \ce{CH3MgBr} \) | Methane (nitroalkane has an acidic alpha hydrogen) |
Cyanides and Isocyanides
Alkyl cyanides (nitriles) are made from alkyl halides with KCN, from amides with \( \ce{P2O5} \) (dehydration), or from a Grignard reagent with cyanogen chloride. Isocyanides are made from alkyl halides with AgCN, or from a primary amine, chloroform and alkali (carbylamine reaction).
| Reagent | Nitrile \( \ce{RCN} \) gives | Isocyanide \( \ce{RNC} \) gives |
|---|---|---|
| \( \ce{H2/Pd} \), \( \ce{Na/C2H5OH} \), \( \ce{LiAlH4} \) | \( \ce{RCH2NH2} \) (primary amine) | \( \ce{RNHCH3} \) (secondary amine) |
| \( \ce{SnCl2/HCl} \), then \( \ce{H3O+} \) | Aldehyde (Stephen reduction) | Not applicable |
| \( \ce{RMgBr} \), then \( \ce{H3O+} \) | Ketone | Not applicable |
| Hydrolysis with \( \ce{H3O+} \) | Amide, then carboxylic acid | Primary amine and formic acid |
Reactions of Nitrobenzene
Nitrobenzene is a pale yellow oily liquid with an almond smell (oil of mirbane). The nitro group is deactivating and meta directing, so electrophilic substitution is slow and gives meta products.
| Reagent | Product |
|---|---|
| Conc. \( \ce{HNO3} \) + conc. \( \ce{H2SO4} \), heat | 1,3-Dinitrobenzene |
| Fuming \( \ce{H2SO4} \) | 3-Nitrobenzenesulphonic acid |
| \( \ce{Cl2/AlCl3} \) | 3-Chloronitrobenzene |
The product of reduction depends on the medium.
| Medium or reagent | Product |
|---|---|
| Strongly acidic (\( \ce{Sn/HCl} \), \( \ce{Fe/HCl} \), \( \ce{H2/Pd} \)) | Aniline |
| Neutral (\( \ce{Zn/NH4Cl} \)) | Phenylhydroxylamine |
| Dilute \( \ce{H2SO4} \), electrolysis | Aniline |
| Conc. \( \ce{H2SO4} \), electrolysis | Phenylhydroxylamine, which rearranges to p-aminophenol |
| Alkaline (\( \ce{Zn/NaOH} \) in water) | Azobenzene |
| \( \ce{Na3AsO3/NaOH} \) or \( \ce{CH3OH/NaOH} \) | Azoxybenzene |
| \( \ce{Zn/NaOH} \) in methanol | Hydrazobenzene |
Key Points to Remember
1. Selective reduction of one nitro group in m-dinitrobenzene is done with ammonium sulphide (or sodium hydrogen sulphide), giving m-nitroaniline.
2. Mulliken–Barker test: nitro compounds are reduced with zinc and ammonium chloride to the hydroxylamine, which reduces Tollens' reagent to give a silver mirror.
3. Bimolecular reduction products (azoxy, azo, hydrazo) appear only in neutral or alkaline medium.
4. Aromatic amines couple with diazonium ions only in weakly acidic medium; phenols need weakly alkaline medium.
5. Isocyanides have the nitrogen bonded to carbon of the alkyl group and have a strong, unpleasant smell.
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