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The Cannizaro Reaction

A Phenol C6H5...

Question

A Phenol $(C_{6} H_{5} O H)$ contains $- O H$ group(s) directly attached to $s p^{2}$ hybridized carbon atom(s) of an aromatic system.
The carbon- oxygen bond length in phenol is slightly less than that in methanol.
Phenol can be prepared by various means such as through alkali fusion of sulphonates, hydrolysis of diazonium salts etc. Commercially it is prepared from Dow's process.

Which of the following can produce phenol?

A

Reduction of aniline

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B

Reduction of chlorobenzene

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C

Oxidation of cumene followed by hydrolysis

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D

Acidification of chlorobenzene

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Solution

The correct option is C Oxidation of cumene followed by hydrolysis
Oxidation of Cumene in presence of air gives cumene hydroperoxide which is converted to phenol and acetone by treating with dilute acid.

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(C_{6} H_{5} O H)

- O H

group(s) directly attached to

s p^{2}

hybridized carbon atom(s) of an aromatic system.
The carbon- oxygen bond length in phenol is slightly less than that in methanol.
Phenol can be prepared by various means such as through alkali fusion of sulphonates, hydrolysis of diazonium salts etc. Commercially it is prepared from Dow's process.
The ionisation constant of phenol is higher than that of ethanol because:

(C_{6} H_{5} O H)

- O H

group(s) directly attached to

s p^{2}

hybridized carbon atom(s) of an aromatic system. In phenols the

- O H

group is attached to

s p^{2}

hybridized carbon of an aromatic ring.
The carbon- oxygen bond length in phenol is slightly less than that in methanol.
Phenol can be prepared by various means such as through alkali fusion of sulphonates, hydrolysis of diazonium salts etc. Commercially it is prepared from Dow's process.

The name of product which is obtained by the decarboxylation of sodium salt of salicylic acid with soda-lime is:

Q. Phenols are compounds in which a hydroxyl group is bonded directly to an

s p^{2}

hybridized carbon atom of an aromatic ring. It is more acidic than an alcohol, but less acidic than a carboxylic acid. It is even less acidic than carbonic acid but more acidic than water. Thus, phenol is unable to protonate

H C O_{3}^{-}

anion but easily protonates

O H^{-}

O H^{-}

group activates the benzene ring so much that electrophilic substitution takes place readily.

The correct order of acidity of the following substituted phenols is:

The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why ?

The reactions of phenol with metals, as well as

N a O H

indicates that it is relatively more acidic than alcohol and water. This is explained on the basis of the structure of phenol. The

s p^{2}

hybridized carbon attached to oxygen being more electronegative than

s p^{3}

hybridized carbon of alcohol, decreases the electron density of oxygen. Because of this oxygen, it develops more electron seeking character and releases proton by taking the shared pair of electrons with it. The acidic nature of phenol can also be explained on the basis of resonance stabilization of phenoxide ion.

What is the hybridisation of carbon which is attached to oxygen in phenol?

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