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Phenols: Structure and Acidity
Phenols have an -OH group on an sp2 carbon of a benzene ring. Phenol is a weak acid, stronger than alcohols because the phenoxide ion is stabilised by resonance: the negative charge is spread over oxygen and the ortho and para carbons. Electron-withdrawing groups (\( \ce{NO2} \), -Cl) increase the acidity, and electron-donating groups (\( \ce{CH3} \)) decrease it, so picric acid is far stronger than phenol and cresols are weaker.
Phenol is stronger than alcohols but weaker than carboxylic acids and carbonic acid. It therefore dissolves in NaOH but not in \( \ce{NaHCO3} \); this separates phenols from carboxylic acids.
Preparation of Phenol
| Starting material | Reagents |
|---|---|
| Chlorobenzene | aqueous NaOH, 623 K, 300 atm, then acid (Dow process) |
| Sodium benzenesulphonate | fusion with NaOH at about 623 K, then acid |
| Benzenediazonium chloride | warm water |
| Cumene | \( \ce{O2} \) gives hydroperoxide, then dilute acid gives phenol and acetone |
| Sodium salicylate or benzoate | soda lime, heat (decarboxylation) |
Reactions of Phenol
| Reaction | Conditions and product |
|---|---|
| Salt formation | NaOH gives sodium phenoxide; Na gives phenoxide and \( \ce{H2} \) |
| Ester formation | acetyl chloride or acetic anhydride gives phenyl acetate |
| Williamson synthesis | phenoxide + \( \ce{CH3I} \) gives anisole |
| Bromination | bromine water gives 2,4,6-tribromophenol (white precipitate); \( \ce{CS2} \), low temperature gives mainly 4-bromophenol |
| Nitration | dilute \( \ce{HNO3} \) gives o- and p-nitrophenol; conc. \( \ce{HNO3} \) gives picric acid |
| Kolbe-Schmidt | phenoxide + \( \ce{CO2} \), 400 K, 4-7 atm, then acid gives salicylic acid |
| Reimer-Tiemann | \( \ce{CHCl3} \) + aqueous NaOH gives salicylaldehyde (via dichlorocarbene) |
| Coupling | benzenediazonium chloride gives p-hydroxyazobenzene |
| Zinc dust distillation | reduces phenol to benzene |
| Oxidation | air or \( \ce{CrO2Cl2} \) gives p-benzoquinone |
Neutral \( \ce{FeCl3} \) gives a violet colour with phenol, which is used as a test. Phenol with phthalic anhydride and conc. \( \ce{H2SO4} \) gives phenolphthalein, and the Liebermann nitroso test (green, red, then blue colour) is also characteristic.
Ethers
Ethers have the general formula R-O-R'. They are made by bimolecular dehydration of primary alcohols with conc. \( \ce{H2SO4} \) at 413 K and by Williamson synthesis (\( \ce{RONa + R'X -> ROR' + NaX} \)), which works best with primary alkyl halides. Tertiary halides give alkenes by elimination. Aryl ethers such as anisole are made from a phenoxide and an alkyl halide, not from an aryl halide.
Ethers are polar but cannot form hydrogen bonds with each other, so their boiling points are much lower than those of isomeric alcohols. They are fairly unreactive. They behave as Lewis bases and form oxonium salts with strong acids.
| Reaction | Product |
|---|---|
| Hot conc. HI, excess, with diethyl ether | two molecules of ethyl iodide |
| Alkyl aryl ether + HI | phenol and alkyl iodide (C-O bond of the alkyl group breaks) |
| Anisole + \( \ce{CH3COCl} \)/\( \ce{AlCl3} \) | 4-methoxyacetophenone (ring is activated, ortho/para substitution) |
| Anisole + \( \ce{Br2} \) in \( \ce{CH3COOH} \) | 4-bromoanisole |
In unsymmetrical ethers with a tertiary alkyl group, cleavage by HI proceeds by an SN1 mechanism and the tertiary iodide forms. With primary and secondary groups, the iodide attacks the smaller group (SN2).
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