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Chapter 16: Q 3P (page 486)

How many products might be formed on chlorination of o-xylene (o-dimethylbenzene), m-xylene, and p-xylene?

Short Answer

Expert verified

Chlorination of o-xylene

Chlorination of meta-xylene

Chlorination of para-xylene

Step by step solution

01

Xylene

Xylene or dimethyl benzene is an aromatic compound that contains two methyl groups attached as substituents to the ring. It has three types of isomers as follows:

02

Chlorination of o, m, and p-xylene

In o-xylene, the two methyl groups are ortho/ para directing in nature. The methyl group shows a +I (inductive) effect and it activates the incoming group at the o/p position in the ring. Chlorination of o-xylene results in two products as shown:

Chlorination of meta-xylene results in three products as shown:

In the case of p-xylene, there are two methyl groups in the opposite position to each other, so the incoming chlorine group could join at only one position and a single ortho product is formed which is as shown:

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Most popular questions from this chapter

Phenylboronic acid,C6H5B(OH)2 , is nitrated to give 15% ortho substitution product and 85% meta. Explain the meta-directing effect of theB(OH)2 group.

Question: Predict the major products of the following reactions:

(a) Nitration of bromobenzene

(b) Bromination of nitrobenzene

(c) Chlorination of phenol

(d) Bromination of aniline

Melamine, used as a fire retardant and a component of the writing surface of white boards, can be prepared from s-trichlorotriazine through a series of SNAr reactions with ammonia. The first substitution takes place rapidly at room temperature. The second substitution takes place near 100 掳C, and the third substitution requires even higher temperature and pressure. Provide an explanation for this reactivity.

Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of AlCl3. Propose a mechanism for the reaction.

Use Figure 16-11 to explain why Friedel鈥揅rafts alkylations often give polysubstitution but Friedel鈥揅rafts acylations do not.
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