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Chapter 3: Problem 90

The conversion of cumene hydroperoxide to phenol and acetone involves (a) an oxidative process (b) a 1,2 -phenyl migration (c) Friedel-Crafts alkylation (d) keto-enol tautomerism

Short Answer

Expert verified
Answer: None of the above processes (Oxidative process, 1,2 -phenyl migration, Friedel-Crafts Alkylation, Keto-enol tautomerism). The correct process involved is the cleavage reaction.

Step by step solution

01

1. Reviewing the options

First, let's review the processes mentioned in the options: (a) Oxidative process: Involves the gain of oxygen or loss of hydrogen in a molecule. (b) 1,2 -phenyl migration: Involves the movement of a phenyl group from one carbon atom to the adjacent carbon atom. (c) Friedel-Crafts Alkylation: A reactions where an alkyl group is introduced in an aromatic ring in the presence of a strong Lewis acid catalyst. (d) Keto-enol tautomerism: A dynamic equilibrium between two isomeric forms, keto and enol, in which a hydrogen atom shifts from one oxygen atom to another.
02

2. Review the reaction mechanism of cumene hydroperoxide conversion to phenol and acetone

Cumene is synthesized from benzene and propylene. Cumene hydroperoxide is synthesized with the help of the free radical process from cumene when exposed to air. This cumene hydroperoxide undergoes a process called cleavage to produce phenol and acetone. We have: Cumene hydroperoxide -> Phenol + Acetone The reaction mechanism for this involves forming a heterolytic bond between the oxygen atom and the carbon atom, which leads to the generation of phenol and acetone.
03

3. Identifying the correct option

Now that we have an understanding of the reaction mechanism of cumene hydroperoxide conversion to phenol and acetone, we can compare it with the processes mentioned in the options. By examining the reaction mechanism, we can see that it does not involve an oxidative process, a 1,2-phenyl migration, Friedel-Crafts alkylation, or keto-enol tautomerism. Since the cumene hydroperoxide is split into two parts (phenol and acetone), it is evident that the process involves a cleavage reaction and not any of the processes mentioned in the options (a) to (d). Therefore, the answer is none of the above processes, and it is advised to check the problem statement or options to ensure the correct process is included.

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Most popular questions from this chapter

Anisole is not formed in the reaction (a) phenol \(+\mathrm{CH}_{3} \mathrm{Br} \stackrel{\mathrm{NaOH}}{\longrightarrow}\) (c) phenol \(+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{SO}_{4} \stackrel{\mathrm{NaOH}}{\longrightarrow}\)

The increasing order of acid strength of 4-Methoxyphenol (I), 4Nitrophenol (II) and 4-Methylphenol (III) is (a) \(\mathrm{III}<\mathrm{I}<\mathrm{II}\) (b) \(\mathrm{I}<\mathrm{II}<\mathrm{III}\) (c) \(I<\mathrm{III}<\mathrm{II}\) (d) \(\mathrm{III}<\mathrm{II}<\mathrm{I}\)

An aromatic compound having the molecular formula \(\mathrm{C}_{8} \mathrm{H}_{10}\) gave only one mono nitro derivative on nitration. The compound is (a) ethyl benzene (b) o-xylene (c) \(\mathrm{m}\) -xylene (d) p-xylene

The correct order of activating influence of the following groups when attached to benzene ring is (a) \(-\mathrm{O}^{-}>-\mathrm{OCOCH}_{3}>-\mathrm{OH}>-\mathrm{COCH}_{3}\) (b) \(-\mathrm{O}^{-}>-\mathrm{OH}>-\mathrm{OCOCH}_{3}>-\mathrm{COCH}_{3}\) (c) \(-\mathrm{OH}>-\mathrm{O}^{-}>-\mathrm{OCOCH}_{3}>-\mathrm{COCH}_{3}\) (d) \(-\mathrm{OH}>-\mathrm{OCOCH}_{3}>-\mathrm{O}^{-}>-\mathrm{COCH}_{3}\)

Which of the following reagents cannot be used to distinguish between benzyl alcohol and phenol? (a) \(\mathrm{FeCl}_{3}\) (b) \(\mathrm{NaOH}\) (aqueous) (c) \(\mathrm{Br}_{2} / \mathrm{CCl}_{4}\) (d) \(\mathrm{NaHCO}_{3}\) solution
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