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Chapter 3: Problem 78

The reaction of phenol with \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{SO}_{4}\) (dimethyl sulphate) in alkaline solution gives (a) o-cresol (b) \(\mathrm{p}\) -cresol (c) a mixture of o and \(\mathrm{p}\) -cresol (d) anisole

Short Answer

Expert verified
Answer: The product of this reaction will be a mixture of o-cresol and p-cresol.

Step by step solution

01

Write down the reaction

Phenol reacts with dimethyl sulphate (\(\mathrm{(CH}_3)_2 \mathrm{SO}_4\)) in the presence of an alkaline solution. Reaction: Phenol + \(\mathrm{(CH}_3)_2 \mathrm{SO}_4\) (in alkaline solution) \(\rightarrow\) ?
02

Determine the mechanism of the reaction

The above reaction is an electrophilic aromatic substitution reaction, where the electrophile, in this case, is dimethyl sulphate, and the substrate is phenol. In an alkaline solution, the phenol gets deprotonated, generating a phenoxide ion that is more reactive. The electrophile \(\mathrm{(CH}_3)_2 \mathrm{SO}_4\) will get attacked by the phenoxide ion in ortho or para positions.
03

Possible products of the reaction

Since the phenoxide ion can attack the electrophile at both the ortho position (position 2) and the para position (position 4), two possible products can be formed: 1. o-cresol (2-methylphenol) 2. p-cresol (4-methylphenol)
04

Choose the correct answer

In this case, the reaction will yield a mixture of o-cresol and p-cresol. Answer: (c) a mixture of o and p-cresol

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Most popular questions from this chapter

The reaction of 4 -hydroxybenzene sulphonic acid with excess bromine water gives (a) 3 -Bromo-4-hydroxybenzenesulphonic acid (b) 3,5 -Dibromo-4-hydroxybenzenesulphonic acid (c) \(2,4,6\) -Tribromophenol (d) 4-Bromobenzenesulphonic acid

Which of the following structures is not aromatic?

The compound (A) when treated with methanol and few drops of conc.H \(_{2} \mathrm{SO}_{4}\) gives the smell of oil of winter green. The compound (A) is (a) phenol (b) benzene (c) \(\mathrm{p}\) -cresol (d) salicylic acid

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

Statement 1 Pure phenol is a colourless solid but turns reddish brown on keeping. and Statement 2 Phenol is slowly oxidized by air to quinone.
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