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Chapter 22: Problem 123

Polychlorinated dibenzo-p-dioxins (PCDDs) are highly toxic substances that are present in trace amounts as by-products of some chemical manufacturing processes. They have been implicated in a number of environmental incidents—for example, the chemical contamination at Love Canal and the herbicide spraying in Vietnam. The structure of dibenzo-pdioxin, along with the customary numbering convention, is The most toxic PCDD is 2,3,7,8-tetrachloro-dibenzo-p-dioxin. Draw the structure of this compound. Also draw the structures of two other isomers containing four chlorine atoms.

Short Answer

Expert verified
The structure of 2,3,7,8-tetrachloro-dibenzo-p-dioxin is: ``` O O 1/ \ / \6 /___\ /___\ 2-Cl O- Cl-5 \ | / \ |7 / \|_ /8 Cl- | -Cl \|/ 4 ``` Two other isomers containing four chlorine atoms are: Isomer 1: 1,2,7,8-tetrachloro-dibenzo-p-dioxin: ``` Cl O O / \ / \ / \6 //___\ /___\ 2-> 3<-O- 5 1\___| -/ \ |7 / \|_ /8 Cl- | -Cl \|/ 4 ``` Isomer 2: 1,2,6,7-tetrachloro-dibenzo-p-dioxin: ``` Cl O O / \ / \ / \6 //___\ /___\ 2-> 3<-O- Cl-5 1\___| -/ \ |7 / \|_ /8 Cl- | -/ \|/ 4 ```

Step by step solution

01

Understand the structure of dibenzo-p-dioxin

Dibenzo-p-dioxin consists of two benzene rings connected through two oxygen atoms. In the customary numbering convention, we start numbering the carbon atoms of the first ring with 1, continue in the clockwise direction, and then switch to the second ring, continuing the numbering: ``` O O 1/ \ / \6 /___\ /___\ 2 O- 5 \ | / \ |7 / \|_ /8 | \|/ 4 ``` The numbering 1 to 8 will help us identify where the chlorine atoms are attached to the molecule.
02

Draw the structure of 2,3,7,8-tetrachloro-dibenzo-p-dioxin

To draw the structure of 2,3,7,8-tetrachloro-dibenzo-p-dioxin, we need to add chlorine atoms to the carbon atoms at positions 2, 3, 7, and 8. Following the numbering convention and the structure above, the structure will be: ``` O O 1/ \ / \6 /___\ /___\ 2-Cl O- Cl-5 \ | / \ |7 / \|_ /8 Cl- | -Cl \|/ 4 ```
03

Draw the structures of two other isomers containing four chlorine atoms

To determine other isomers containing four chlorine atoms, we can change the position of some chlorine atoms while following the numbering convention. Here are two examples: Isomer 1: 1,2,7,8-tetrachloro-dibenzo-p-dioxin: ``` Cl O O / \ / \ / \6 //___\ /___\ 2-> 3<-O- 5 1\___| -/ \ |7 / \|_ /8 Cl- | -Cl \|/ 4 ``` Isomer 2: 1,2,6,7-tetrachloro-dibenzo-p-dioxin: ``` Cl O O / \ / \ / \6 //___\ /___\ 2-> 3<-O- Cl-5 1\___| -/ \ |7 / \|_ /8 Cl- | -/ \|/ 4 ``` These are two other isomers containing four chlorine atoms as requested in the exercise.

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Most popular questions from this chapter

Reagents such as \(\mathrm{HCl}\) , HBr, and $\mathrm{HOH}\left(\mathrm{H}_{2} \mathrm{O}\right)$ can add across carbon-carbon double and triple bonds, with \(\mathrm{H}\) forming a bond to one of the carbon atoms in the multiple bond and \(\mathrm{Cl}\) , Br, or OH forming a bond to the other carbon atom in the multiple bond. In some cases, two products are possible. For the major organic product, the addition occurs so that the hydrogen atom in the reagent attaches to the carbon atom in the multiple bond that already has the greater number of hydrogen atoms bonded to it. With this rule in mind, draw the structure of the major product in each of the following reactions.

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