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MHT-CET : Chemistry Entrance Exam

MHT - CET : Chemistry - Organic Hydroxy Compounds Page 2

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Phenols (Carbolic Acids)


The organic, aromatic, hydroxy compounds in which one or more hydroxyl (-OH) groups are directly attached to the carbon of the aromatic ring are called phenols.
The simplest member of the family is phenol or carbolic acid or benzenol or hydroxy benzene.



Preparation of Phenols


(a) From Chlorobenzene:


Dow's Process
It is a nucleophilic substitution reaction.



Rasching's Process
It is a nucleophilic substitution reaction


b) From Benzenesulphonic Acid:

c) From Cumene Isopropyl Benzene or 2-phenyl Propane:



Physical Properties of Phenol


  1. Pure phenol is a colourless, hygroscopic, crystalline solid.
  2. It has a characteristic phenolic odour.
  3. When exposed to air and light, it turns pink due to partial oxidation.
  4. It has m.p. = 316K, and b.p. = 455K.
  5. It is partially soluble in water but readily soluble in ethanol and ether.
  6. It is acidic in nature and is weakly acidic compared to carboxylic acid.



Chemical Properties of Phenol


a) Halogenation:
During bromination, bromonium ion (Br+) acts as the reacting species.
    (i) Reaction with Bromine Water

    (ii) Reaction with Bromine in Carbon Disulphide

b) Nitration:
During nitration of phenols, nitronium ion (NO2+) acts as the reacting species. It is obtained by using nitrating mixture (conc. H2SO4 and conc. HNO3).

    (i) Reaction with Dilute Nitric Acid

    (ii) Reaction with Conc. Nitric Acid (or Nitrating Mixture)

c) Sulphonation:

    (i) Reaction with Conc. H2SO4 at Low Temperature (300K):

    (ii) Reaction with Conc. H2SO4 at High Temperature (373K)



Test to Distinguish Between a Phenol and an Alcohol




Uses of Phenol


  1. It is an anti-septic and a disinfectant. Hence, it is used in medicated soaps, skin ointments and lotions.
  2. It is used to prepare phenolic resins and plastics. Examples: phenol formaldehyde resin and bakelite plastic.
  3. It is used to prepare compounds like picric acid, salicylic acid, catechol.
  4. It is also used to prepare drugs and dyes.


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