Scribd
Upload
360 views12 pages

Acidity of Phenol & Alcohol

The document discusses the acidity of phenol, alcohols, and other organic compounds. It explains that (1) phenol is more acidic than water or alcohols due to resonance stabilization of the phenoxide ion, (2) the presence of electron donating groups increases acidity by making the conjugate base more stable, and (3) phenol can be distinguished from alcohols through its reaction with sodium hydroxide and characteristic color changes with iron (III) chloride and bromine solutions.

Uploaded by

Hafizszulfeyzul Feyzul
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd
360 views12 pages

Acidity of Phenol & Alcohol

The document discusses the acidity of phenol, alcohols, and other organic compounds. It explains that (1) phenol is more acidic than water or alcohols due to resonance stabilization of the phenoxide ion, (2) the presence of electron donating groups increases acidity by making the conjugate base more stable, and (3) phenol can be distinguished from alcohols through its reaction with sodium hydroxide and characteristic color changes with iron (III) chloride and bromine solutions.

Uploaded by

Hafizszulfeyzul Feyzul
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd
You are on page 1/ 12

Acidity of phenol & alcohol

The presence of R (EDG) make CH3CH2O- is


e- richer than OH- and make it less stable,
thus H2O > acidic than CH3CH2OH
Phenol > acidic than H2O & CH3CH2OH
because phenoxide ion formed is more
stable
The phenoxide ion formed is stabilised by
resonance effect
Acidity of phenol & alcohol

O H O -
release proton
+ H+

Phenoxide ion
Phenoxide ion stability

O - O O O
- -

O-
- -

-
Example:

OH CH2CH2-OH CH2-OH OH

acidity increase
Example:

COOH OH

> > CH CH -OH


3 2
ACIDITY
DECREASE

Na2CO3 KOH K, Na
NaHCO3 NaOH NaH
Weak bases Strong bases Very strong bases
Exercise

Arrange the following compounds in order


of increasing acidity.
( a ) Water , butanol , phenol , methanol

( b ) pronanol , 2-methylphenol ,
4-nitrophenol , 3-nitrophenol
Reaction of Phenol:
(i) Reaction with Sodium

eg:

C6H5-OH + Na C6H5-O-Na+ + H2
(ii) Reaction with NaOH

eg:

C6H5-OH + NaOH C6H5-O-Na+ + H2O


note:
aliphatic alcohol does not react with
NaOH because alcohol is a weaker acid
compared to phenol (phenoxide ion is
more stable compared to alxoxide ion).
Because of this, NaOH is often used as a
chemical test to differentiate alcohol with
phenol.
OH O-Na+

+ NaOH + H2O

(soluble)formed
Observation: 1 layer solution

OH

+ NaOH insoluble in water

Observation: 2 layers solution formed


Phenol Test:
(i) Using aqueous FeCl3 (yellow in
colour)
- Turn the yellow to purple complex.
OH OH
+ FeCl
3

FeCl3
(ii) Using aqueous Bromin (brown)
- white precipitate forms.

OH OH
Br Br
+ 3Br2 / H2O +
3HBr
Br

You might also like