Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 27: Problem 39

Predict the main product(s) of (a) the mononitration of chlorobenzene; (b) the monosulfonation of nitrobenzene; (c) the monochlorination of 1-methyl-2-nitrobenzene

Short Answer

Expert verified
The products are: (a) 1-Chloro-3-nitrobenzene; (b) 1-Nitro-3-benzenesulfonic acid; (c) 1-Chloro-2-methyl-3-nitrobenzene.

Step by step solution

01

Understand the Mononitration of Chlorobenzene

The nitration of chlorobenzene involves the addition of a nitro group (NO2) to the chlorobenzene molecule. Since the chlorine atom is deactivating and meta-directing, the nitro group will attach at the meta position relative to the chlorine atom.
02

Predict the Monosulfonation of Nitrobenzene

Sulfonation involves the introduction of a sulfonic acid group (SO3H) into an organic compound. In this case, the existing substituent on the benzene ring, a nitro group, is strongly deactivating, and therefore directs new substituents to the meta position. Thus, the sulfonic acid group will attach itself to the meta position relative to the nitro group.
03

Determine the Monochlorination of 1-Methyl-2-nitrobenzene

In this case, there are two substituents already present: a methyl group (which is activating and ortho/para-directing) and a nitro group (which is deactivating and meta-directing). The conflict between the two substituents must be resolved. The power of the nitro group as a deactivator usually prevails over the methyl group as an activator. This will lead to the introduction of a chlorine atom at the position next to the methyl group (ortho position) is favored.

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

Answer the following questions for this E2 reaction: $$\begin{aligned} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{NaOH} & \longrightarrow \mathrm{CH}_{3} \mathrm{CH}= \mathrm{CH}_{2}+\mathrm{NaBr}+\mathrm{H}_{2} \mathrm{O} \end{aligned}$$ (a) What is the rate expression for the reaction? (b) Draw the reaction profile for the reaction. Label all parts. Assume that the products are lower in energy than the reactants. (c) What is the effect on the rate of the reaction of doubling the concentration of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br} ?\) (d) What is the effect on the rate of the reaction of halving the concentration of \(\mathrm{NaOH} ?\)

Give the major product that forms when (Z)-3-methyl2-pentene reacts with each of the following reagents: (a) \(\mathrm{HI} ;\) (b) \(\mathrm{H}_{2}\) in the presence of a platinum catalyst; (c) \(\mathrm{H}_{2} \mathrm{O}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4} ;\) (d) \(\mathrm{Br}_{2}\) in \(\mathrm{CCl}_{4}\).

Indicate the principal product(s) you would expect in (a) treating \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) with dilute \(\mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq})\) (b) exposing a mixture of chlorine and propane gases to ultraviolet light; (c) heating a mixture of isopropyl alcohol and benzoic acid; (d) oxidizing sec-butyl alcohol with \(\mathrm{Cr}_{2} \mathrm{O}_{7}^{2-}\) in acidic solution.

Draw a structure to represent the principal product of each of the following reactions: (a) 1 -pentanol \(+\) dichromate ion (acid solution) (b) butyric acid + ethanol (acid solution) (c) 2 -methyl-1-butene \(+\mathrm{HBr}\)

Write the formulas of the products expected to form in the following situations. If no reaction occurs, write N.R. (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}(\mathrm{aq})+\mathrm{HCl}(\mathrm{aq}) \longrightarrow\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}(\mathrm{aq})+\mathrm{HBr}(\mathrm{aq}) \longrightarrow\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{3}^{+}(\mathrm{aq})+\mathrm{H}_{3} \mathrm{O}^{+}(\mathrm{aq}) \longrightarrow\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{3}^{+}(\mathrm{aq})+\mathrm{OH}^{-}(\mathrm{aq}) \longrightarrow\)
See all solutions

Recommended explanations on Chemistry Textbooks

Kinetics

Read Explanation

Organic Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Physical Chemistry

Read Explanation

Making Measurements

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