Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 3: Problem 187

The major product formed when o-cresol is treated with \(\mathrm{Br}_{2}\) in \(\mathrm{CS}_{2}\) at ice cold conditions is

Short Answer

Expert verified
Answer: The major product formed in this reaction is 2-bromo-o-cresol.

Step by step solution

01

Identify the electrophile and nucleophile

In an electrophilic aromatic substitution reaction, the benzene ring acts as a nucleophile, attacking an electrophile. Here, the electrophile is the bromine ion (\(\mathrm{Br}^{+}\)) formed from the \(\mathrm{Br}_{2}\). The nucleophile is the aromatic ring of the o-cresol molecule.
02

Analyze the directing influence of the hydroxyl group

In the o-cresol molecule, the hydroxyl group (OH) is an ortho/para director. It can activate the carbon atoms in the ortho and para positions on the benzene ring, making them more susceptible to electrophilic attack. Because the reaction takes place under ice cold conditions, it is likely that the reaction will proceed faster at the ortho position.
03

Determine the ortho-substituted product

Under these conditions, the o-cresol molecule undergoes electrophilic substitution with the bromine ion at the ortho position, forming a new C-Br bond. The new compound will have the hydroxyl group (OH) at one position, and the bromine atom (Br) at the adjacent carbon atom on the benzene ring. This compound is called 2-bromo-o-cresol.
04

Conclusion

The major product formed when o-cresol is treated with \(\mathrm{Br}_{2}\) in \(\mathrm{CS}_{2}\) at ice cold conditions is the ortho-substituted product, 2-bromo-o-cresol.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

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

Phenol is more acidic than ethanol because (a) greater resonance stabilization of phenoxide ion (b) phenol has greater H-bonding than ethanol (c) phenol has larger molar mass (d) phenol has higher boiling point than ethanol

Give the major product of mono nitration of the following compounds. Justify each case.

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.

The major product formed by the reaction of \(\mathrm{N}\) -phenylbenzamide with \(\mathrm{Br}_{2} / \mathrm{Fe}\) is
See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Making Measurements

Read Explanation

Kinetics

Read Explanation

The Earths Atmosphere

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free