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Chapter 22: Problem 50

There are three isomers of dichlorobenzene, one of which has now replaced naphthalene as the main constituent of mothballs. a. Identify the ortho, the meta, and the para isomers of dichlorobenzene. b. Predict the number of isomers for trichlorobenzene. c. It turns out that the presence of one chlorine atom on a benzene ring will cause the next substituent to add ortho or para to the first chlorine atom on the benzene ring. What does this tell you about the synthesis of m-dichlorobenzene? d. Which of the isomers of trichlorobenzene will be the hardest to prepare?

Short Answer

Expert verified
a. Ortho-dichlorobenzene has chlorines on adjacent carbon atoms, meta-dichlorobenzene has one carbon atom between the chlorines, and para-dichlorobenzene has two carbon atoms between the chlorines. b. There are 3 possible isomers for trichlorobenzene: 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene. c. The synthesis of m-dichlorobenzene is not favored because it does not follow the ortho or para pattern. d. The isomer of trichlorobenzene with chlorines at positions 1, 3, and 5 (1,3,5-trichlorobenzene) should be the hardest to prepare.

Step by step solution

01

a. Identifying the ortho, meta, and para isomers of dichlorobenzene

Dichlorobenzene has a benzene ring with two chlorine substituents. The three possible isomers have the chlorine atoms at different positions relative to each other. Ortho-dichlorobenzene has the chlorines on adjacent carbon atoms; meta-dichlorobenzene has one carbon atom between the chlorines, and para-dichlorobenzene has two carbon atoms between the chlorines.
02

b. Predicting the number of isomers for trichlorobenzene

Trichlorobenzene has a benzene ring with three chlorine substituents. We can create the different isomers by systematically adding chlorine atoms to the benzene ring. The first isomer has chlorines at positions 1, 2, and 3 (adjacent to each other). The second isomer has chlorines at positions 1, 2, and 4. The third isomer has chlorines at positions 1, 3, and 5. Therefore, there are 3 possible isomers for trichlorobenzene.
03

c. Synthesis of m-dichlorobenzene

The fact that a chlorine atom on a benzene ring causes the next substituent to add ortho or para to the first chlorine atom indicates that the synthesis of m-dichlorobenzene is not favored. This is because the synthesis follows a specific pattern (ortho or para), and m-dichlorobenzene does not fit that pattern.
04

d. Determining the hardest isomer of trichlorobenzene to prepare

Considering the information from part (c), it is reasonable to assume that a similar pattern exists for trichlorobenzene. The isomer with chlorines at positions 1, 3, and 5 does not follow the ortho or para pattern, as there are two carbon atoms between each chlorine. Therefore, the isomer of trichlorobenzene with chlorines at positions 1, 3, and 5 (1,3,5-trichlorobenzene) should be the hardest to prepare.

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