Account for the following: 1. Phenol does not react with NaHCO_3 whereas carboxylic acids react. 2. Phenol is more easily nitrated than benzene.

1. RCOOH+NaHCO_3 RCOONa+H_2CO_3 Weaker acid than RCOOH Such acid-base reaction takes place only if the acid formrd is weaker than the reacting acid. In other words, phenol is not a strong enough acid to react with NaHCO_3. 2. Nitration involves attack of electrophile nitronium ion + NO_2 on benzene ring. Due to +R effect of -OH group electron density on benzene increases. Therefore, phenol is more easily nitrated as compared to benzene.

Account for the following: 1. Phenol does not react with NaHCO_3 …

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Question

Account for the following:

Phenol does not react with $\ce{NaHCO_3}$ whereas carboxylic acids react.
Phenol is more easily nitrated than benzene.

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Answer

$\text{RCOOH}+\text{NaHCO}_3\xrightarrow{ \ \ \ \ \ \ \ \ \ }\text{RCOONa}+\text{H}_2\text{CO}_3$
$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Weaker acid}$
$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{than RCOOH}$

Such acid$-$base reaction takes place only if the acid formrd is weaker than the reacting acid. In other words, phenol is not a strong enough acid to react with $\ce{NaHCO_3}.$

Nitration involves attack of electrophile nitronium ion $\stackrel{{+ \ \ \ }}{\hbox{ NO}_2}$ on benzene ring. Due to $+R$ effect of $-OH$ group electron density on benzene increases. Therefore, phenol is more easily nitrated as compared to benzene.