/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q2P Propose a mechanism for the alum... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 17: Q2P (page 849)

Propose a mechanism for the aluminum chloride-catalyzed reaction of benzene with chlorine.

Short Answer

Expert verified

The mechanism for the aluminum chloride-catalyzed reaction of benzene with chlorine is as follows:

Step by step solution

01

Chlorination of benzene

The chlorination of benzene works much like bromination except whenAlCl3 is used as a Lewis acid catalyst.It is an electrophilic aromatic substitution.

02

Mechanism of the aluminum chloride-catalyzed reaction

In the first step, theCl2 attacks theAlCl3 .

Cl2attacks theAlCl3

In the second step, the benzene attacks the product formed in the first step.AlCl4_and chlorobenzene carbocation is formed, in which the positive charge delocalizes at the 1st, 3rd, and 5th positions. The chloride ionAlCl4_ of makes a bond with the H of benzene and forms HCl. The other product formed is chlorobenzene.

Mechanism of the aluminum chloride-catalyzed reaction

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.

Over 30 million students worldwide already upgrade their learning with 91影视!

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

Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solution results. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears. Suggest a structure for the bright yellow species, and explain this unusual behavior.

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.

Reagents Desired Product

(a) benzene + n-butyl bromide n-butylbenzene

(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene

(c) bromobenzene + ethyl chloride p-bromoethylbenzene

(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide

(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)

To synthesize m-ethylbenzenesulfonic acid, a student attempted the Friedel鈥揅rafts alkylation of benzenesulfonic acid with bromoethane. Do you predict that this reaction was successful? If not, propose an alternative synthesis.

m-ethylbenzenesulfonic acid

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels鈥揂lder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 掳C, an interesting Diels鈥揂lder adduct of the formula C20H14results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and a broad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings of anthracene reacted as a diene.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Making Measurements

Read Explanation

Organic Chemistry

Read Explanation

Kinetics

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.