it contain preparation and reaction of phenol

1. Preparation and Reaction of
Phenol

2. PREPARATION OF PHENOL

3. In Dow's process method chlorobenzene
is heated with aq. NaOH at about 623k and
300 atm. pressure to form sodium
phenoxide, which is acidified by dilute acid
like HCl to form phenol.

4. To prepare phenol, cumene is first oxidized
in the presence of air of cumene hydro-
peroxide. Then, cumene hydroxide is
treated with dilute acid to prepare
phenol and acetone as by-products.

5. Fusion of sodium benzene sulfonate
with solid NaOH at 300 C followed by
treatment with dilute HCl

6. Warming a solution of benzene
diazonium chloride prepared from
aniline on a water bath at 50C

7. From Coal tar
• Coal tar provides natural source of phenol and
cresol.
• The middle oil fraction of coal tar contains
phenols, cresols and naphthalene.[ 170-240 C]
• Oil when cooled solid naphthalene deposit.
• Centrifuge and the oil left out is agitated with
NaOH gives phenols and cresols.

8. REACTION OF PHENOL

9. Formation of salt
Phenol is acidic It react with sodium
hydroxide or sodium metal to form
salts

10. Phenol is weakly acidic than carboxylic
acid. It does not react with sodium
carbonate and sodium bi cabonate

11. Reaction with FeCl3 phenol give violet
colour on treatment with FeCl3 due to
formation of complex. This reaction is
given by most of the phenols

12. Formation of esters- alkali react with
phenol to form phenoxide which will
react with acid chloride to form phenyl
esters

13. Formation of ether- phenol react with
alkyl halide in alkali solution form
phenyl ethers.

14. Phenol distilled with zinc dust yield
benzene in low amount

15. Halogenation: Phenol with bromine in
water give precipitate of 2,4,6
tribromo phenol. Chlorine behave in
the same manner

16. Halogenation: Phenol with bromine in
CS2/CCl4 give precipitate of 2,4,6
tribromo phenol. Chlorine behave in
the same manner

17. Nitration : Phenol on nitration with
dilute nitric acid gives a mixture of
ortho and para nitro phenol

18. Nitration : Phenol on nitration with
Concentrated nitric acid gives a
mixture of ortho and para nitro phenol

19. Sulfonation : when phenol react with
concentrated sulphuric acid at 20 C ,
Ortho phenolsulfonic acid is the main
product and at 100 C, Para phenol
sulfonic acid is the main product

20. Reimer Tiemann reaction of phenol

21. Reimer Tiemann reaction of phenol
The Reimer Tiemann reaction is an organic
chemical reaction where phenol is converted
into an ortho hydroxy benzaldehyde using
chloroform, a base, and acid workup. This
name reaction can also be described as the
chemical reaction used for the ortho-
formylation of phenols.

22. Mechanism of Reimer Tiemann
reaction

23. Mechanism of Reimer Tiemann
reaction
• Chloroform (1) is deprotonated by a strong
base (normally hydroxide) to form the
chloroform carbanion (2)
• It will quickly alpha-eliminate to
give dichlorocarbene (3); this is the principal
reactive species.
• The hydroxide will also deprotonate the
phenol (4) to give a negatively charged
phenoxide (5).

24. Mechanism of Reimer Tiemann
reaction
• The negative charge is delocalised into the
aromatic ring, making it far more nucleophilic.
• Nucleophilic attack on the dichlorocarbene
gives an intermediate dichloromethyl
substituted phenol (7).
• After basic hydrolysis, the desired product (9)
is formed.

25. The Kolbe–
Schmitt reaction or Kolbe process
(named after Hermann Kolbe and
Rudolf Schmitt)

26. Kolbe’s process is a carboxylation
chemical reaction that proceeds by heating
sodium phenoxide (the sodium salt of phenol)
with carbon dioxide under pressure (100 atm,
125 °C), then treating the product with sulfuric
acid.

28. • The Kolbe reaction can be classified as a carboxylation
chemical reaction. The reaction occurs when sodium
phenoxide is allowed to absorb carbon dioxide and the
resulting product is heated at a temperature of a 125-
degree celsius and a pressure of over a hundred
atmospheres. An unstable intermediate is now formed.
• This unstable intermediate goes through a proton shift,
leading to the formation of sodium salicylate. Now, this
mixture is treated with sulfuric acid. The acidification
of the mixture yields the salicylic acid.

29. Gattermann Reaction- it involves the
treatment of phenol with a mixture of
hydrogen cyanide and hydrogen
chloride in the presence of aluminium
chloride as catalyst . Salicylic acid is
formed.

30. Fries rearrangement
• When ester of phenols heated with AlCl3 the
acyl group migrates from the phenolic oxygen
to an ortho or para position of the ring thus
yielding a ketone

31. Phenol couple with benzene
diazonium chloride in alkaline medium
form P-hydroxyazobenzene

32. Phenol with phthalic anhydride in the
presence of sulfuric acid to form
phenolphthalein

33. Reaction of phenol with formaldehyde