Question

Which of the following statements is/are correct?

• A. The nitration of phenol is faster than phenyl acetate.
• B. The reaction of $PhO ^{\odot}$ is faster than with $PhCH _{2} Cl$.
• C. Base-catalysed hydrolysis of $p$-nitrophenyl 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 is 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).

Basic and nucleophilic character:

Since, $PhO ^{\Theta}$ is a stronger nucleophile than $p-NC - C _{6} H _{4} O ^{\Theta}$. Hence, it reacts faster with $PhCH _{2} Cl$.

As we know, (I) is faster than (II). The $\bar{e}$-withdrawing effect of $\left(p- NO _{2}\right)$ group $(- R$ and $- I )$, from $O$ makes $p- NO _{2}- C _{6} H _{4}- O ^{\ominus}$ a weaker base and better leaving group.
(4) Esterification of $PhOH$ is faster than $p$-nitrophenol. Phenol, a less acidic compound (or more basic) is more reactive in acidic conditions. With its $\bar{e}_{\text {-withdrawing }}$ $\left(p- NO _{2}\right)$ group, $p$-nitrophenol is less basic and less reactive.