Question

Which of the following statements is/are correct?

• A. The nitration of phenol is faster than phenyl acetate
• B. The reaction of $Ph{O}^{\ominus }$ is faster than
• C. Base-catalysed hydrolysis of $p$-nitrphenyl acetate is faster than phenyl acetate
• D. Acid-catalysed esterification of $PhOH$ is faster than $p$-nitrophenol with $MeCOOH$

Answer 1

Answer: (A), (B), (C), (D)

1. Correct. SE reaction if favoured by EDG; less favoured by EWG

Due to cross-conjugation in (II), $\bar{e}$-donating power of oxygen to the ring decreases and hence it is less reactive than (I)

Since, $Ph{O}^{\ominus }$ is a stronger nucleophile than $p-$ $NC-C_6{H}_4{O}^{\ominus }$. Hence, it reacts faster with $PhC{H}_{2}Cl$

As we know,(I) is faster than (II). The $\bar{e}-$ withdrawing effect of $\left(p-N{O}_2\right)$ group $(-R$ and $-$ I), from $O$ makes $p-N{O}_2-C_6{H}_4-O^{\ominus }$ a weaker
base and better leaving group
d. Esterification of $PhOH$ is faster than $p$ nitrophenol phenol, a less acidic compound (or more basic) is more reactive in acidic conditions. With its $\bar{e}-$ withdrawing $(p$ - $N{O}_2)$ group, $p$ nitrophenol is less basic and less reactive