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Question

Which of the following statements is/are correct?


A
The nitration of phenol is faster than phenyl acetate
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B
The reaction of PhO is faster than pNCC6H4O with PhCH2Cl.
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C
Base-catalysed hydrolysis of p-nitrophenyl acetate is faster than phenyl acetate
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D
Acid-catalysed esterification of PhOH is faster than p-nitrophenol with MeCOOH
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Solution

The correct options are
A Acid-catalysed esterification of PhOH is faster than p-nitrophenol with MeCOOH
B The nitration of phenol is faster than phenyl acetate
C The reaction of $$\displaystyle PhO^{\circleddash }$$ is faster than $$\displaystyle p-NC-C_{6}H_{4}O^{\circleddash }$$ with $$\displaystyle PhCH_{2}Cl.$$
D Base-catalysed hydrolysis of p-nitrophenyl acetate is faster than phenyl acetate
A. Due to cross-conjugation in phenol, e-donating power of oxygen to the ring decreases and hence, it is less reactive than phenyl acetate.
B. Since, $$\displaystyle PhO^{\circleddash }$$ is a stronger nucleophile than $$\displaystyle p-NC-C_{6}H_{4}O^{\circleddash }$$. Hence, it reacts faster with $$\displaystyle PhCH_{2}Cl.$$
C. The e-withdrawing effect of $$\displaystyle \left ( p-NO_{2} \right )$$ group from O makes $$\displaystyle p-NO_{2}-C_{6}H_{4}-O^{\circleddash }$$ a weaker base and better leaving group.
D. Esterfication of PhOH is faster than p-nitrophenol. Phenol, a less acidic compound (or more basic) is more reactive in acidic conditions. With its$$\displaystyle \bar{e}$$-withdrawing $$\displaystyle \left ( p-NO_{2} \right )$$ group, p-nitrophenol is less basic and less reactive.

Chemistry

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