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Chapter 3: Problem 178

Statement 1 Phenoxide ion is more reactive than phenol towards electrophiles. and Statement 2 Phenoxide ion is stabilized more by resonance than phenol.

Short Answer

Expert verified
Explain your answer based on resonance stabilization and electron density. Answer: Phenoxide ion is more reactive towards electrophiles than phenol, due to its greater resonance stabilization and higher electron density on the oxygen atom.

Step by step solution

01

Understanding phenol and phenoxide ion

Phenol is an aromatic compound with a hydroxyl group (-OH) attached to the benzene ring. When phenol loses the hydrogen ion (H+) from the hydroxyl group, it forms a phenoxide ion.
02

Explaining reactivity towards electrophiles

Electrophiles are species that accept an electron pair from nucleophiles. In this case, phenol and phenoxide ion can act as nucleophiles since they have electrons to donate. The reactivity of phenol and phenoxide ion towards electrophiles depends on the stability of the intermediate formed during the reaction and electron density on the oxygen atom.
03

Drawing resonance structures for phenol and phenoxide ion

Now, let's draw the resonance structures for phenol and phenoxide ion to understand their stability. For phenol, the resonance structures are as follows:\[ \begin{array}{rl} &\chemfig{[:-30] *6(-=(-@{O}\lewis{1:3:5:,O}-(H))-=-=(-))}\\\longleftrightarrow{} &\chemfig{[:-30] *6(-=(-@{O}\lewis{3:5:,O})-=-(-)=(-))} \end{array} \]For phenoxide ion, the resonance structures are as follows:\[ \begin{array}{rl} &\chemfig{[:-30] *6(-=(-@{O}\lewis{0:2:4:6:,^{-1}O})-=-=(-))}\\\longleftrightarrow{} &\chemfig{[:-30] *6(-=(-@{O}\lewis{2:4:6:,^{-1}O})-=-(-)=(-))} \end{array} \]
04

Evaluating resonance stabilization

By looking at the resonance structures, we can see that the negative charge on the oxygen atom in phenoxide ion is delocalized over the benzene ring, providing more resonance stabilization. In phenol, the lone pair on oxygen is not as delocalized due to the presence of the hydrogen, leading to comparatively less resonance stabilization.
05

Comparing reactivities towards electrophiles

Since the phenoxide ion has more electron density on the oxygen atom and is more stabilized by resonance, it is more reactive towards electrophiles as it can easily donate an electron pair. In contrast, phenol is less reactive as it has less electron density on the oxygen atom and its resonance stabilization is also less compared to phenoxide ion. Now we can conclude that the given statements are true: Phenoxide ion is more reactive than phenol towards electrophiles due to its greater resonance stabilization and electron density on the oxygen atom.

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