Phenol is a type of aromatic compound in which the hydrogen on the aromatic hydrocarbon ring is replaced by a hydroxyl group (-OH). The general formula is ArOH. Simple phenol is phenol. According to the number of hydroxyl groups contained in its molecule, it can be divided into monohydric phenol, dihydric phenol and polyphenol (three or more phenolic hydroxyl groups).
The phenolic hydroxyl group is directly connected to the sp2 hybridized carbon atom of the benzene ring, which is very similar to the enol in aliphatic compounds. In addition, due to the conjugation effect of the unshared electron pair of the hydroxyl oxygen atom of the phenol with the benzene ring, not only the phenol becomes a stable compound, but also the dissociation of the phenol is favorable. It is worth noting that the type of hydroxyl oxygen atom hybridization of phenol is unequal sp2 hybridization, which is different from the unequal sp3 hybridization of alcohol hydroxyl oxygen atoms.
The physical properties
Most phenols are colorless needle-like crystals or white crystals, and a few alkyl phenols are high-boiling liquids; they have a special odor, which turns red when exposed to air and light, and changes color faster when exposed to alkali.
Low-grade phenols have a special pungent odor, especially for eyes, respiratory tract mucosa, skin, etc., which have a strong irritation and corrosion effect. Safety protection measures should be taken when using. Some phenols have strong bactericidal ability. For example, Lysol, the disinfectant used in hospitals, is an aqueous solution of mixed cresol.
Although phenol can undergo two types of reactions, C-O bond and O-H bond breaking, due to the p-π conjugation effect, the C-O bond is very strong and not easy to break. However, the O-H bond is easily broken, because the negative charge in the generated phenol anion can be delocalized and dispersed and stabilized. The benzene ring on phenol is easier to undergo electrophilic substitution reaction than benzene due to the above-mentioned conjugation.
The color reaction
Most phenols can react with dilute aqueous solutions of ferric chloride. Different phenols react with ferric chloride to show different colors. For example, phenol, resorcinol, 1,3,5-benzenetriol and ferric chloride solution are all purple; cresol is blue; catechol and hydroquinone are green; 1, 2 , 3-Benzenetriol is red, α-naphthol is purple precipitate, β-naphthol is green precipitate, etc. This color reaction is often used to identify the presence of phenols.
Compounds with a structure in which a hydroxyl group is connected to a sp2 hybrid carbon atom (—C=C—OH) structure can show a special color in an aqueous solution of FeCl3. The general alcoholic hydroxyl group does not have this reaction, so it can also be used to distinguish alcohols from enols.
The oxidation reaction
Phenols are easily oxidized, but the products are complex. Pure phenol is a colorless crystal that can be gradually oxidized to pink, red or dark red after being placed in the air. If phenol is strongly oxidized with acid potassium dichromate, p-benzoquinone is formed.
Catechol and hydroquinone are more easily oxidized to the corresponding quinones than phenol, but resorcinol cannot be oxidized to the corresponding quinones. Quinones generally have a color.
The friedel-Crafts reaction
Phenol is also prone to Friedel-Crafts acylation and alkylation reactions. However, the phenolic hydroxyl group requires aluminum trichloride to act to form an aluminum salt, so more aluminum trichloride is needed to catalyze the reaction to obtain p- and o-acylphenol. Hydrogen bonds can be formed between the hydrogen of the phenolic hydroxyl group in the o-acylphenol and the acyl oxygen atom, which makes it more soluble in non-polar solutions. Using this feature, recrystallization can be used to separate this isomer.
Friedel-Crafts reaction requires nitrobenzene or carbon disulfide as solvent. If peng trifluoride is used as catalyst, phenol and carboxylic acid can also directly react to obtain acyl phenol.
Phenol and phthalic anhydride undergo the above-mentioned acylation reaction under the action of concentrated sulfuric acid or anhydrous zinc chloride. Two molecules of phenol and one molecule of acid anhydride are condensed to obtain phenolphthalein. Z is a commonly used acid-base indicator. Phenolphthalein is a colorless liquid in a solution with a pH of less than 8.5. When the pH is greater than 9, a pink conjugated dianion with a large range of charge delocalization is formed. The alkylation reaction of phenol is generally carried out with alcohol or olefin catalyzed by concentrated sulfuric acid, and the reaction is not easy to control in the mono-substitution stage.
Weak acid
Acidity comparison: carbonic acid>phenol>bicarbonate>water.
Phenol is more acidic than alcohol, because the O-H bond of the phenolic hydroxyl group is easy to break, and the generated phenoxy anion is relatively stable, which makes the dissociation equilibrium of phenol tend to the right side, which shows weak acidity. In addition to the hydrogen of phenolic hydroxyl group can be replaced by metal, it can also form salt (such as sodium phenolate) and water with strong alkali solution.
If carbon dioxide is introduced into the aqueous solution of sodium phenol, free phenol will be precipitated. This is because phenol is weaker than carbonic acid, so phenate can be decomposed by carbonic acid.
C6H5ONa+CO2+H2O→C6H5OH+NaHCO3
Since the acidity of phenol is weaker than that of carbonic acid, phenol can only be dissolved in sodium hydroxide but not in sodium bicarbonate. In the laboratory, phenol is often distinguished from carboxylic acid, which is soluble in sodium hydroxide and sodium bicarbonate, based on this characteristic. This method can also be used to separate phenolic and carboxylic acid components in Chinese herbal medicine.
The substitution reaction
The phenolic hydroxyl group is difficult to be substituted due to the p-π conjugation, but the hydrogen atom on the benzene ring can be substituted, and halogenation, nitration and sulfonation reactions occur, and the hydroxyl group is the ortho and para position positioning group, which can activate the benzene ring Therefore, phenol is easier to undergo electrophilic substitution reaction than benzene.
1. The reaction between the aqueous solution of halogenated phenol and bromine water immediately generates white precipitate of tribromophenol, which is commonly used in qualitative or quantitative determination of phenol in environmental testing;
2. Nitrated phenol can be nitrated by dilute nitric acid at room temperature to generate ortho and para nitro compounds. Use dilute nitric acid to generate a mixture of o-nitrophenol and p-nitrophenol. If a mixture of concentrated nitric acid and concentrated sulfuric acid is used as a nitrating agent, dinitrophenol or trinitrobenphenol can be generated.
Compounds with a structure in which a hydroxyl group is connected to a sp2 hybrid carbon atom (—C=C—OH) structure can show a special color in an aqueous solution of FeCl3. The general alcoholic hydroxyl group does not have this reaction, so it can also be used to distinguish alcohols from enols.
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