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The OH group of phenol...

The `OH` group of phenol

A

activates ring powerfully and direacts ortho, para in nucleophilic aromatic substitution.

B

activates ring powerully and direacts ortho, para in electrophilic substitution

C

deactivates powerfully and directs ortho, para in electrophile aromatic substitution

D

deactivates powerfully and directs meta in electrophilic aromatic substitution.

Text Solution

Verified by Experts

The correct Answer is:
B

Like the amino group, the phenolic group powerfully activates aromatic rings toward electrophilic substitution in essentially the same way.

The intermediates are hardly carbocations at all, but rather oxonium ions `(A and B)` in which every atom (except hydrogen ) has a complete octet of electrons. they are formed tremendously faster than the carbocations derived from benzene itsself.
Attack on a phenoxide ion yields an even more stable (and hence even more rapidly formed) intermediate, an unstaturated ketone `(C and D)`

With phenols (as with amines) special precautions must often be taken to prevent polysubstitution and oxidation.
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Explain why is OH group in phenols more strongly held as compared to OH group in alcohols ?

Assertion : Phenol is more reactive than benzene towards electrophilic substitution. Reason : OH group in phenol is ortho and paradirecting in nature.

Knowledge Check

  • STATEMENT-1: Phenol is more reactive than benzene towards electrophilic substitution reaction. and STATEMENT-2: OH group of phenol is electron donating due to resonance.

    A
    Statement-1 is True, Statement-2 is True, Statement-2 is a correct explanation for statement-6
    B
    Statement-1 is True, Statement-2 is True, Statement-2 is NOT a correct explanation for Statement-6
    C
    Statement-1 is True, Statement-2 is False
    D
    Statement-1 is False, Statement-2 is True
  • Because of resonance the oxygen atom of -OH group of phenol

    A
    Acquires positive charge
    B
    Acquires negative charge
    C
    Remains unaffected
    D
    Liberates
  • Because of resonance, the oxygen atom of -OH group of phenol

    A
    acquires positive charge
    B
    acquires negative charge
    C
    remains unaffected
    D
    liberates