Question

Consider p-aminophenol
Which positions are activated for electrophilic aromatic substitution reaction in acidic and basic media respectively?

• A. ${\alpha }^{\prime }$ in A and $\beta$ in B
• B. ${\alpha }^{\prime }$ in A and $\alpha$ in B
• C. ${\beta }^{\prime }$ in A and $\alpha$ in B
• D. ${\beta }^{\prime }$ in A and $\beta$ in B

Answer 1

The correct option is D ${\beta }^{\prime }$ in A and $\beta$ in B

Ref. image $\Rightarrow$ For electrophilic aromatic aubstitution, the electrondensity on the attacking carbon should be high to that it can attack on $E^{\oplus }$ effectively

In (A) Ref. image , $N{H}_4^{\oplus }$ attack $e^{\oplus }$ & increases tur charge density on $\alpha$ position

therefore ${\beta }^{\prime }$ is more suitable position.

In (B) $\Rightarrow$ The resonance of lone pair of $e^{\ominus }$ on O increases $e^{\ominus }$ density at $\beta$ therefore $\beta$ is correct.

$\beta \&{\beta }^{\prime }$