PHENOL

ROLL NO:46 47 50 68 78
INTRODUCTION:

 Defination:

 Compounds containing –OH Group attached directly to an aromatic ring.

 • Aromatic compound, any of a large class of unsaturated (double or triple bond)chemical

compounds.

 Phenol is an aromatic compound. The chemical formula of this organic compound is

C6H6O. Phenol is also known as Carbolic acid.
 • It is mildly acidic and is corrosive to the respiratory tract, eyes, and skin.

 Structure:
 OH group attached to one side of benzene. Molecular Formula C6H5OH or C6H6O.
Derivative of benzene Three double bonds sp2 Hibridization.
Nomenclature

 The simplest hydroxyl derivative of benzene is called Phenol.

 IUPAC NAMING RULES

 Rule1 Give the numbering to carbon atom cyclic compounds of Phenol, considering
the – OH is at C – 1
 Rule 2 Substituent's are indicated why using the number of carbon atom to which
these are attached.
 Rule 3 In IUPAC naming use the phenol word after the substituent's.
 Benzene ring can be substituted by three ways:
  Ortho 1 , 2 substituted
  Meta 1 , 3 substituted
  Para 1 , 4 substituted

 o-cresol m-nitrophenyl
2 – chloro - 4 – Niyro phenol
Benzene - 1 , 2 - diol

1 , 3 – Dihydroxy bezene.
Trihydricphenol
Physical properties:

 1 Phenol is a colourless,deliquescent solid.

 2 It is crystalline in nature.

 3 Its melting point is 41⁰C.

 4 Its boiling point is181.7⁰C.

 5 It has a distinct odour that is sickeningly sweet and tarry.

 6 It is sparingly soluble in water forming pink solution at room temperature (Due to the formation
of HBond).

 7 Phenols are less soluble in alcohols than water.

 8 Phenol is acidic in nature with a ph of 5-6.

 9 Phenol is a COMBUSTIBLE SOLId.

 10 Its is highly poisonous.

Preparation of Phenol:

 DOW’S PROCESS:
 The reactant chlorobenzene is heated with aqueous sodium hydroxide at temperatures
623K and 300atm to get sodium phenoxide ion. Then in the next step sodium phenoxide
ion is treated with Dilute HCl which gives the final product as phenol.
From Diazonium Salts:

 When an aromatic amine is treated with nitrous (NaNO2 + HCl) acid at 160°C, diazonium
salts are obtained.Upon warming with water, these diazonium salts finally hydrolyze to
phenols.
FROM BENZENE SULPHONIC ACID:

 • Benzenesulphonic acid can be obtained from benzene by reacting it with oleum. This
benzene sulphonic acid which is treated with sodium hydroxide at high temperatures for
the formation of sodium phenoxide. Finally, sodium phenoxide on acidification gives
phenol.
FROM GRIGNARD REAGENT:

 • In the presence of dry ether, chlorobenzene or bromobenzene is first transformed into

phenyl magnesium halide. The Grignard reagent produces phenol when it reacts with
oxygen and is then hydrolysed by a mineral acid.
CHEMICAL PROPERTIES:

 Phenol give two types of reactions:

 1. Reactions involving ring:

 Examples:
 a. Hydrogenation b. Sulphonation c. Halogenation

 2. Reactions involving −OH group:

 a. Salt formation b. Reduction with Zn
Reactions involving ring:

 Hydrogenation:
 When hydrogen reacts with phenol at 150℃ in the presence of Ni catalyst it gives
cyclohexanol.
Sulphonation :

 Phenol reacts with H2SO4 at 25℃ and 100℃ to give ortho and para phenolsulphonic acid
respectively.

p-phenolsulphonic acid o-phenolsulphonic acid

Halogenation:

 Phenol reacts with bromine water to give 2,4,6- tribromophenol.

Reactions involving –OH group:

 Salt formation :

 Phenol reacts with alkalies to form salts.

Reduction with zinc :

 Phenol reacts with zinc to give benzene and zinc oxide.

Application or Uses of Phenol:

 It is used as disinfectant in hospitals and washrooms.

 Phenol is included in the production of ear and nose drops.
 It is widely used as antiseptic and disinfectant in several mouth wash, lotion, deodorant
and soap.
 It is used in the manufacturing of drugs like aspirin etc.
 It is used for the manufacturing of resins.
 It is used for the manufacturing of polymers like Bakelite which is used for the
manufacturing of electrical goods like plugs and switches etc.
 It is used for the production of ply-wood.
 It is used for the laboratory preparation of benzene.
 Several commercial compounds are synthesized from precursors containing phenols.
 It is used for the manufacturing of phenolphthalein.
 It is used for the production of nitro derivative of phenol like 2, 4, 6 trinitrophenol (picric
acid) used to make explosives and dyeing wool and silk.