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Chemistry

9th Edition
Steven S. Zumdahl
ISBN: 9781133611097

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Chemistry

9th Edition
Steven S. Zumdahl
ISBN: 9781133611097
Textbook Problem

When toluene (C6H5CH3) reacts with chlorine gas in the presence of iron(III) catalyst, the product is a mixture of the ortho and para isomers of C6H4ClCH3. However, when the reaction is light-catalyzed with no Fe3+ catalyst present, the product is C6H5CH2Cl. Explain.

Interpretation Introduction

Interpretation: An explanation corresponding to the given chemical reaction is to be stated.

Concept introduction: Organic compounds are synthesized through organic reactions. The reactions of toluene with chlorine gas in the presence of iron(III) catalyst, yield the ortho and para isomers of chlorotoluene by aromatic substitution reaction.

To determine: An explanation corresponding to the given chemical reaction.

Explanation

Explanation

The reaction of toluene with chlorine gas in the presence of iron(III) catalyst, yields a mixture of ortho and para isomers of chlorotoluene.

The structural formula of toluene is,

Figure 1

Toluene offers two sites for the reaction where the halogen can attach, the ring and the side chain. The side chain is alkane like end and hence, it undergoes halogenations through free radical substitution reaction.

This reaction requires a condition of high temperature and light under which halogen atom is formed.

The reaction of toluene with chlorine gas is light catalyzed and leads to the production of chlorotoluene.

The reaction is,

CH4+Cl2light CH3Cl+HCl

Figure 2

The ring in benzene undergoes electrophilic substitution

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Ch-22 P-11RQCh-22 P-12RQCh-22 P-1QCh-22 P-2QCh-22 P-3QCh-22 P-4QCh-22 P-5QCh-22 P-6QCh-22 P-7QCh-22 P-8QCh-22 P-9QCh-22 P-10QCh-22 P-11QCh-22 P-12QCh-22 P-13ECh-22 P-14ECh-22 P-15ECh-22 P-16ECh-22 P-17ECh-22 P-18ECh-22 P-19ECh-22 P-20ECh-22 P-21ECh-22 P-22ECh-22 P-23ECh-22 P-24ECh-22 P-25ECh-22 P-26ECh-22 P-27ECh-22 P-28ECh-22 P-29ECh-22 P-30ECh-22 P-31ECh-22 P-32ECh-22 P-33ECh-22 P-34ECh-22 P-35ECh-22 P-36ECh-22 P-37ECh-22 P-38ECh-22 P-39ECh-22 P-40ECh-22 P-41ECh-22 P-42ECh-22 P-43ECh-22 P-44ECh-22 P-45ECh-22 P-46ECh-22 P-47ECh-22 P-48ECh-22 P-49ECh-22 P-50ECh-22 P-51ECh-22 P-52ECh-22 P-53ECh-22 P-54ECh-22 P-55ECh-22 P-56ECh-22 P-57ECh-22 P-58ECh-22 P-59ECh-22 P-60ECh-22 P-61ECh-22 P-62ECh-22 P-63ECh-22 P-64ECh-22 P-65ECh-22 P-66ECh-22 P-67ECh-22 P-68ECh-22 P-69ECh-22 P-70ECh-22 P-71ECh-22 P-72ECh-22 P-73ECh-22 P-74ECh-22 P-75ECh-22 P-76ECh-22 P-77ECh-22 P-78ECh-22 P-79ECh-22 P-80ECh-22 P-81ECh-22 P-82ECh-22 P-83ECh-22 P-84ECh-22 P-85ECh-22 P-86ECh-22 P-87ECh-22 P-88ECh-22 P-89ECh-22 P-90ECh-22 P-91ECh-22 P-92ECh-22 P-93ECh-22 P-94ECh-22 P-95ECh-22 P-96ECh-22 P-97ECh-22 P-98ECh-22 P-99ECh-22 P-100ECh-22 P-101ECh-22 P-102ECh-22 P-103ECh-22 P-104ECh-22 P-105ECh-22 P-106ECh-22 P-107ECh-22 P-108ECh-22 P-109ECh-22 P-110ECh-22 P-111AECh-22 P-112AECh-22 P-113AECh-22 P-114AECh-22 P-115AECh-22 P-116AECh-22 P-117AECh-22 P-118AECh-22 P-119AECh-22 P-120AECh-22 P-121AECh-22 P-122AECh-22 P-123AECh-22 P-124AECh-22 P-125AECh-22 P-126AECh-22 P-127AECh-22 P-128AECh-22 P-129AECh-22 P-130AECh-22 P-131AECh-22 P-132AECh-22 P-133AECh-22 P-134AECh-22 P-135AECh-22 P-136AECh-22 P-137CWPCh-22 P-138CWPCh-22 P-139CWPCh-22 P-140CWPCh-22 P-141CWPCh-22 P-142CWPCh-22 P-143CWPCh-22 P-144CWPCh-22 P-145CPCh-22 P-146CPCh-22 P-147CPCh-22 P-148CPCh-22 P-149CPCh-22 P-150CPCh-22 P-151CPCh-22 P-152CPCh-22 P-153CPCh-22 P-154CPCh-22 P-155CPCh-22 P-156CPCh-22 P-157CPCh-22 P-158CPCh-22 P-159IPCh-22 P-160IPCh-22 P-161MPCh-22 P-162MP

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