Organic chemistry

Phenol | Structure, Preparation, Reactions, Properties | Crack Chemistry

Phenol – General View

Phenol is simplest Aromatic Alcohol with Moleculer formula of C₆H₅OH.
This Molecule consists of Phenyl Group (-C₆H₅) attached with the hydroxy group (-OH).
It is Acidic in Nature,it requires additional carefull handlings due to its acidic nature.

Phenol – Structure

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Structure of Phenol
Molecular Formula : C₆H₅OH
In Phenol,all ring carbon atoms are sp² hybridised and the Oxygen atom of the -OH group is sp³ hybridised
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Hybridisation of Phenol
•  All Ring Carbon Atoms also have a p orbital and there are perpendicular to the plane of the Sigma Bond of the Ring.
•  The Lateral Overlap of these p orbital produces a delocalised π molecular orbital
  There are Two Lone Pair of Electrons are Present in Oxygen Atom in the -OH group

Phenol – Resonance


According to the resonance theory, Phenol is considered to be a hybrid of the following resonance structures.
You can Notice that the Ortho & Para position in the resonance structure has a negative charge.
So Phenol undergoes Electrophilic Substitution reactions (E⁺)
Due to the presence of the -OH group, It undergoes Electrophilic Substitution faster than Benzene.
Because The Hydroxyl group donates the pair electrons to the ring resonance.

Phenol – Preparation

Phenol can be prepared by

From Chlorobenzene (Dow Process)

This involves the hydrolysis of the chlorobenzene with aqueous NaOH at high temperature and pressure followed by treatment with dilute HCl
Dows process,preparation of phenol by dow process
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Dow’s Process
It was first introduced by Dow Chemical Company In U.S.A

Mechanism of Reaction

Dows Process, mechanism of dows Process,
Mechanism of Dow’s Process

Phenol – Electrophilic Substitution reactions


Electrophilic Substitution reactions Listed in this Posts are
•   Halogenation Of Phenol
•   Nitration Of Phenol
•   Sulfonation Of Phenol
•   Formylation Of Phenol (Reimer-Tiemann Reaction)

Halogenation Of Phenol :

Phenol reacts with bromine water (aqueous bromine) to give a precipitate of 2,4,6-tribromophenol.
This Reaction is also used in the laboratory to predict the Saturation/unsaturation Test of Organic Compounds.
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Bromination of Phenol

Nitration Of Phenol :

•   When phenol reacts with Dilute Nitric Acid.
It gives a mixture of o- and p-nitrophenol.
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Nitration Of Phenol
•   When phenol reacts with Excess of Concentrated Nitric Acid. It gives Picric Acid
 
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Nitration Of Phenol – Excess

Sulfonation Of Phenol :

When Phenol is treated with concentrated sulfuric acid at 20°C.It forms o-phenol sulfonic acid as a product
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Sulfonation Of Phenol

Reimer-Tiemann Reaction – Phenol

•  This involves the treatment of Phenol with Chloroform in aqueous Sodium Hydroxide solution followed by acid-hydrolysis.
•  It forms Salicyaldehyde as a product.
•  Carbene Formed as an Intermediate
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Formylation of Phenol
To View Complete Reaction Mechanisms of Reimer Tiemann Reaction – Click Here

Kolbe Reaction – Phenol

This involves the treatment of sodium Phenoxide with carbon dioxide at 125°C under 6 atmospheres of pressure followed by acid-hydrolysis. It forms Salicylic acid at the end of the Reaction.
Phenol - Kolbe Reaction, Phenol
Kolbe Reaction

Phenol – Properties

Phenol is a Colorless, hygroscopic, crystalline solid
• Melting Point of Phenol42°C
• Boiling Point of Phenol182°C
Phenol has a distinctive odor.
Phenol is readily soluble in Ethanol and Organic solvents
• Below 65.8°C Phenol is Only Partially miscible with water but above this temperature, it is miscible in all proportions

Workout Test – Phenol

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