CHEMICAL PROPERTIES AND USES OF PHENOLS

Chemical properties and uses of Phenols

Electrophilic substitution reactions

The presence of OH group on benzene increases the electron density on the benzene ring making it more susceptible to attack by an electrophile. The reactions involving benzene ring are electrophilic substitution reaction. The presence of OH group makes the orthoand para carbon of benzene more electron rich than meta position. The OH group is called ‒, p ‒ directing group.

Electrophilic substitution reactions

Reactions of phenol involving the cleavage of O–H bond

Kolbe’s reaction:

Kolbe’s reaction

Reimer-Tiemann reaction:

Reimer-Tiemann reaction

Fries rearrangement:

Esters of phenol gives phenolic ketones on rearrangement in the presence of anhydrous AlCl3. This reaction is called fries rearrangement.

Fries rearrangement

Acetylation:

Acetylation

Nitration:

Reaction with dilute HNO3 :

Reaction with dilute HNO3

Reaction with conc. HNO3 :

Reaction with dilute HNO3

Halogenation:

Bromination in solvents of low polarity like CS2 :

Halogenation

The reaction of phenol with bromine water:

The reaction of phenol with bromine water

Reactions of phenol involving cleavage of the C-O bond

Reaction with zinc dust

Reaction with zinc dust

Reaction with ammonia:

Reaction with ammonia

Uses of phenol

  • It is used as an antiseptic.
  • It is used as a disinfectant in household cleaners.
  • It is used in the preparation of resins, dyes, explosives, lubricants, pesticides, plastics, drugs, etc.

 

ASSIGNMENT : CHEMICAL PROPERTIES AND USES OF PHENOLS ASSIGNMENT MARKS : 10  DURATION : 1 week, 3 days

 

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