About phenol:

Phenol is the simplest member of a family of compounds in which an -OH group is attached
directly to a benzene ring. Molecular formula of phenol is C6H5OH.It is an organic compound.
White crystalline solid and volatile. Compound’s that contain an –OH group in a side chain
attached to an aromatic ring are not phenols. They are called aromatic alcohols. Careful handling
because it can cause chemical burns.

Uses of Phenol:

1. About half of the total world’s production of phenol is used for making phenol-formaldehyde
resin.
2. Phenol is used as a starting material for- drugs such as aspirin.
3. Several dyes.
4. Explosives.
5. Wood preservatives.
6. Herbicides.
7. Nylon and
8. Anticeptics.

Industrial uses:

Important industrial commodity as a precursor to many materials and useful compounds.

Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies,
Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous
pharmaceutical drugs.

electrical nonconductivity and heat-resistant properties in electrical insulators, radio and

telephone casings, kitchenware, jewelry, pipe stems, children's toys, and firearms.

Names of laboratory preparation for phenol:

1.Dow process (from chlorobenzene).

2.From Sodium benzene sulphonate.
3. From Benzene diazonium salts.

Dow process:

1.Preparation of chlorobenzene:
Benzene can be easily converted to chlorobenzene by electrophilic aromatic substitution. Ferric
chloride was used as a catalyst.
2. Hydrolysis of chlorobenzene:
Chlorobenzene is treated with aqueous NaOH at 350 °C and 150atm or molten sodium hydroxide
at 350 °C to convert it to sodium phenoxide.
3.Acidification of sodium phenoxide:
Sodium phenoxide yields phenol upon acidification by H+/H2O.
From Sodium benzene sulphonate:

This involves fusion of sodium benzene sulphonate with solid NaOH at 300°C followed by
treatment with dilute HCl. From aromatic sulfonic acids by melting with NaOH at high
temperature. And prepared alkyl-substituted phenols which was limited.

Physical Properties of Phenol:

1. Most pure phenols are colorless liquids or solids, although they are often found to contain a
red tint owing to the presence of oxidation products.
2. It has to be handled with great care because it causes immediate white blistering to the skin.
3. Phenol is moderately soluble in water.
4. The boiling point of phenols is higher than aliphatic alcohols of comparable molecular
weights. This is due to stronger intermolecular hydrogen bonding in phenols relative to alcohols.
5. Phenol is slightly acidic in nature.

Industrial Process of Phenol Preparation:

Industrial process from readily available cumene (isopropyl-benzene). Forms cumene

hydroperoxide with oxygen at high temperature. Converted into phenol and acetone by acid.

Acidity of Phenol/Acidity of phenol and alcohol:

Phenols are much more acidic than alcohols but less so than carboxylic acids or even carbonic
acid. Phenols are acidic due to the formation of stable phenoxide ions in aqueous solutions.
phenol itself gives phenoxide ion on dissociation. Phenol reacts with sodium hydroxide solution
to give a colorless solution containing sodium phenoxide. In that reaction, the hydrogen ion has
been removed by the strongly basic hydroxide ion in the sodium hydroxide solution. Phenols are
much more acidic(pka~10) than alcohols(pka~16) due to resonance stabilization of the
phenoxide ion. Phenols react with NaOH solutions but alcohols do not. forming soluble salts that
are soluble in dilute aqueous solution.

Acidity of substituted phenol:

Substituted phenol can be more or less acidic than phenol itself. Because of an electron-
withdrawing substituent makes a phenol more acidic by delocalizing the negative charge.
Phenols with an electron-donating substituent are less acidic, because these substituents
concentrate the charge.

Chemical properties of phenol/ Reactions of phenol:

The hydroxyl group is a strongly activating, making phenols substrates for electrophilic
halogenation, nitration, sulfonation, and Friedel–Crafts reactions. Reaction of a phenol with
strong oxidizing agents yields a quinone. Fremy's salt [(KSO3)2NO] works under mild
conditions through a radical mechanism.

Reaction with benzene diazonium chloride:

Phenol couples with benzene diazonium chloride in an alkaline solution to form p-hydroxy azo
benzene. which is a known dye color and mostly used.

Summary of phenol:

1.Phenol is much more acidic (pKa ~ 10) than alcohols.

2.Substitution of the aromatic ring by an electron-withdrawing group increases phenol acidity.
3.Substitution by an electron-donating group decreases acidity.
4.Oxidized to quinones.
5.Quinones are reduced to hydro-quinones.

Solubility of phenol:

Phenol is soluble in water to some extent. It is due to its ability to form hydrogen bonding with
water molecules. A hydrogen bond is an attraction between two atoms that already participate in
other chemical bonds. One of the atoms is hydrogen, while the other may be any electronegative
atom, such as oxygen, chlorine, or fluorine. However the large part of phenol molecule is phenyl
group that is non polar and hence its solubility if limited in water. However the polarity of this
part too increases in phenoxide ion. Also water and phenol has same sp3 hybridization.

Increasing boiling points of phenol:

Phenol is made by 2 types of bond, they are

1.Hydrozen bond
2. Van der Waals bond or dispersion forces
Hydrogen bonding will be much the same for all the phenols, but the dispersion forces will
increase as the phenols get bigger. As the molecules get longer and have more electrons, these
attractions (Van der Waals dispersion forces) get stronger. It takes more energy to overcome the
dispersion forces, and so the boiling points rise. Hence the boiling point is increase as the
number of carbon atoms in the chains increases.

Why phenols have higher boiling point than similar alkanes and alkyl halides?

1. Hydrogen bonds set up between the slightly positive hydrogen atoms and lone pairs on
oxygens in other molecules.
2. The hydrogen atoms are slightly positive. As the bonding electrons are pulled away from them
towards the very electronegative oxygen atoms.
3. Hydrogen bonds are much stronger than van der Waals dispersion forces. It takes more energy
to separate phenol molecules than it does to separate alkane molecules.