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Chapter 3: Problem 143

The reagent used to convert phenol to quinol is (a) \(\mathrm{KMnO}_{4} / \mathrm{H}_{2} \mathrm{SO}_{4}\) (c) \(\mathrm{K}_{2} \mathrm{~S}_{2} \mathrm{O}_{8}\) followed by acidification

Short Answer

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(a) KMnO4 / H2SO4 (b) K2S2O8 followed by acidification Answer: (b) K2S2O8 followed by acidification

Step by step solution

01

Determine the products of phenol reacting with the given reagents

We will determine the products formed upon reaction of phenol with the given two reagents in separate cases.
02

Case 1: Phenol reaction with \(\mathrm{KMnO}_{4} / \mathrm{H}_{2} \mathrm{SO}_{4}\)

\(\mathrm{KMnO}_{4}\) is a strong oxidizing agent and it can oxidize phenol to produce a benzoquinone. The reaction is as follows: C\(_6\)H\(_5\)OH + 2 KMnO\(_4\) + 3 H\(_2\)SO\(_4\) \(\longrightarrow\) C\(_6\)H\(_4\)O\(_2\) + 2 MnSO\(_4\) + 8 H\(_2\)O + K\(_2\)SO\(_4\) In this reaction, the quinol is not formed.
03

Case 2: Phenol reaction with \(\mathrm{K}_{2} \mathrm{~S}_{2} \mathrm{O}_{8}\) followed by acidification

\(\mathrm{K}_{2} \mathrm{~S}_{2} \mathrm{O}_{8}\) is a peroxydisulfate oxidizing agent. It can oxidize phenol to form ortho-quinol as a major product. The reaction is as follows: C\(_6\)H\(_5\)OH + \(\mathrm{K}_{2} \mathrm{~S}_{2} \mathrm{O}_{8}\) \(\longrightarrow\) C\(_6\)H\(_{4}\)(OH)\(_2\) + \(\mathrm{K}_{2} \mathrm{~SO}_{4}\) In this reaction, the ortho-quinol is formed as a product.
04

Select the correct reagent for converting phenol into quinol

According to the reactions mentioned above, the reagent that successfully converts phenol into quinol is: (c) \(\mathrm{K}_{2} \mathrm{~S}_{2} \mathrm{O}_{8}\) followed by acidification

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Most popular questions from this chapter

Reaction of benzene with isobutene in presence of sulphuric acid gives mainly

Which of the following statements is correct about phenols? (a) Electron releasing groups increases acidic character (b) Electron withdrawing substituents decreases acidic character (c) Phenol is less resonance stabilized than phenoxide ion. (d) Phenol turns red litmus blue

Which among the following is more acidic than phenol? (a) o-methoxy phenol (b) \(\mathrm{m}\) -methoxy phenol (c) p-methoxyphenol (d) none of these

Which of the following compound will not give benzoic acid on refluxing with alkaline \(\mathrm{KMnO}_{4}\) followed by acidification?

Why is ortho fluoro phenol a weaker acid than ortho chlorophenol?
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