Paaras Thakur

Phenols
Lecture 3
 Telegram
APP

tinyurl.com/jeelivechat
LIVE Plus Classes
Test Series / Quizzes
Doubt Clearing Sessions
Most Personalized
The trouble is,
You think
you have TIME
- Buddha
Expense
SAVE Energy

Time
We Give You Choice

Learn what you want and How you want

Online vs Offline
Step 1 Step 2

INSTALL
Step 3 Step 4
IIT JEE
Step 5 Step 6

JEELIVE

22,500
Claisen Rearrangement

Healing allyl phenyl ether to 2000c effects an intramolecular reaction to generate

o - allylphenol.

Mechanism:
Example What are compounds A and B in the following sequence?
Claisen Rearrangement

When the ortho position is occupied, rearomatization can’t take place.

Fries Rearrangement

Phenolic esters of aliphatic and aromatic carboxylic acids, when treated with
a Lewis acid as catalyst, do undergo a rearrangement reaction to yield ortho- and
para-acylphenols respectively.
Fries Rearrangement
Reimer - Tiemann Reaction

A. Formylation

Carbene generation:
Reimer - Tiemann Reaction

Addition of dichlorocarbene and hydrolysis:

Reimer - Tiemann Reaction

B. Carboxylation
Reaction with Neutral FeCl3

Phenols generate colours like violet, red, green or white appearance when treated
with neutral FeCl3.

Even salicylic acid with a

phenolic group gives violet
colour with neutral FeCl3.

Benzoic acid doesn’t give

this test.
Gattermann Aldehyde Synthesis

It is a chemical reaction in which aromatic compounds are formylated by a

mixture of hydrogen cyanide (HCN) and hydrogen chloride (HCl) in the presence
of a Lewis acid catalyst such as AlCl3.
Some More Reactions

Ni / 3H2
Δ

Zn Dust
Δ
Example Phenol, when it first reacts with concentrated sulphuric acid and then with
concentrated nitric acid, gives

a. 2,4,6-trinitrobenzene. (AIEEE 2008)

b. o-nitrophenol.
c. p-nitrophenol.
d. nitrobenzene.
Example The major product obtained on interaction of phenol with sodium hydroxide and
carbon dioxide is
(AIEEE 2009)
a. benzoic acid.
b. salicylaldehyde.
c. salicylic acid.
d. phthalic acid.
Example Phenol is heated with a solution of mixture of KBr and KBrO3.
The major product obtained in the above reaction is
(AIEEE 2011)
a. 3-bromophenol.
b. 4-bromophenol.
c. 2,4,6-tribromophenol.
d. 2-bromophenol.
Example Nitrophenol is less soluble in water than p- and m-nitrophenols because

a. o-nitrophenol is more volatile in steam than those of m and p-isomers.

b. o-nitrophenol shows intramolecular hydrogen bonding.
c. o-nitrophenol shows intermolecular hydrogen bonding.
d. melting point of o-nitrophenol is lower than those of m and p-isomers.

(AIEEE 2012)
Example The following reaction
(JEE Main Online 2014)

a. Perkin reaction.
b. Gattermann−Koch formylation
c. Kolbe’s reaction.
d. Gattermann reaction.
IIT JEE
JEELIVE