Chapter 22: Problem 34

There are three compounds with the formula \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{Cl}_{3}\) in which three of the hydrogen atoms of the benzene molecule have been replaced by chlorine atoms. Draw structures for these compounds.

Short Answer

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Answer: The three isomers of the compound C6H3Cl3 are: 1. 1,2,3-trichlorobenzene (also known as ortho-isomer) 2. 1,2,4-trichlorobenzene (also known as meta-isomer) 3. 1,3,5-trichlorobenzene (also known as para-isomer)

Step by step solution

Knowing the benzene structure

In order to draw the isomers of the compound, we must first understand the structure of the benzene molecule. Benzene has a hexagonal ring structure with each carbon atom bonded to two other carbon atoms and one hydrogen atom. All carbon-carbon bonds in the ring are equivalent with a bond order between a single bond and a double bond, known as resonance.

Replacing hydrogen atoms with chlorine atoms

In our compound, three hydrogen atoms are replaced by chlorine atoms. We'll create different isomers based on the position of the chlorine atoms with respect to each other.

Creating the first isomer (1,2,3-Trichlorobenzene)

In the first isomer, we replace three consecutive hydrogen atoms with chlorine atoms. The isomer is called 1,2,3-trichlorobenzene, also known as the ortho-isomer, and its structure is: ``` Cl Cl \ / C === C // \ C === C--Cl \ / H H ```

Creating the second isomer (1,2,4-Trichlorobenzene)

In the second isomer, we replace hydrogen atoms at positions 1, 2, and 4 with chlorine atoms. The resulting isomer is 1,2,4-trichlorobenzene or meta-isomer, and its structure is: ``` Cl Cl \ / C === C // \ C--Cl === C \ / H H ```

Creating the third isomer (1,3,5-Trichlorobenzene)

In the third isomer, we replace hydrogen atoms at positions 1, 3, and 5 with chlorine atoms. This isomer is called 1,3,5-trichlorobenzene or para-isomer, and its structure is: ``` Cl H \ / C === C // \ C--Cl === C--Cl \ / H H ``` So, the three possible isomers corresponding to \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{Cl}_{3}\) are 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene.

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There are three compounds with the formula \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{Cl}_{3}\) in which three of the hydrogen atoms of the benzene molecule have been replaced by chlorine atoms. Draw structures for these compounds.

Short Answer

Step by step solution

Knowing the benzene structure

Replacing hydrogen atoms with chlorine atoms

Creating the first isomer (1,2,3-Trichlorobenzene)

Creating the second isomer (1,2,4-Trichlorobenzene)

Creating the third isomer (1,3,5-Trichlorobenzene)

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