Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 22: Problem 113

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 The most toxic \(\mathrm{PCDD}\) 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
id=3980520&get=image∈=yes&m=1&w=300&h=300&scale=1) ![1,2,3,7-tetrachloro-dibenzo-p-dioxin](https://www.chemspider.com/ImagesHandler.ashx?id=232444&get=image∈=yes&m=1&w=300&h=300&scale=1)

Step by step solution

01

Draw Dibenzo-p-dioxin structure

To draw the structure of a PCDD (Dibenzo-p-dioxin), we must have two benzene rings (also known as phenyl groups) connected through two oxygen atoms. The standard numbering of carbon atoms in the dibenzo-p-dioxin structure is clockwise, starting from the carbon adjacent to the first oxygen atom.
02

Draw 2,3,7,8-tetrachloro-dibenzo-p-dioxin

Now, we will draw the structure of the most toxic PCDD which is 2,3,7,8-tetrachloro-dibenzo-p-dioxin. To do this, we need to replace the hydrogen atoms at positions 2, 3, 7, and 8 with chlorine atoms. The structure will look like this: ![2,3,7,8-tetrachloro-dibenzo-p-dioxin](https://upload.wikimedia.org/wikipedia/commons/thumb/0/08/2%2C3%2C7%2C8-Tetrachlorodibenzodioxin_structure.png/300px-2%2C3%2C7%2C8-Tetrachlorodibenzodioxin_structure.png)
03

Draw the first isomer with four chlorine atoms

In this step, we will draw an isomer of 2,3,7,8-tetrachloro-dibenzo-p-dioxin with four chlorine atoms. One possible isomer can have chlorine atoms at positions 1, 2, 6, and 7. The structure of 1,2,6,7-tetrachloro-dibenzo-p-dioxin would look like this: ![1,2,6,7-tetrachloro-dibenzo-p-dioxin](https://www.chemspider.com/ImagesHandler.ashx?id=3980520&get=image∈=yes&m=1&w=300&h=300&scale=1)
04

Draw the second isomer with four chlorine atoms

In this final step, we will draw another isomer with four chlorine atoms. This isomer can have chlorine atoms at positions 1, 2, 3, and 7, resulting in the structure of 1,2,3,7-tetrachloro-dibenzo-p-dioxin which would look like this: ![1,2,3,7-tetrachloro-dibenzo-p-dioxin](https://www.chemspider.com/ImagesHandler.ashx?id=232444&get=image∈=yes&m=1&w=300&h=300&scale=1)

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

How many different pentapeptides can be formed using five different amino acids?

Give two examples of saturated hydrocarbons. How many other atoms are bonded to each carbon in a saturated hydrocarbon?

The two isomers having the formula \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}\) boil at \(-23^{\circ} \mathrm{C}\) and \(78.5^{\circ} \mathrm{C}\). Draw the structure of the isomer that boils at \(-23^{\circ} \mathrm{C}\) and of the isomer that boils at \(78.5^{\circ} \mathrm{C}\).

Reagents such as \(\mathrm{HCl}, \mathrm{HBr}\), 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 \(\mathrm{Cl}, \mathrm{Br}\), 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. a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{H}_{2} \mathrm{O} \stackrel{\mathrm{H}^{*}}{\longrightarrow}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{HBr} \longrightarrow\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}+2 \mathrm{HBr} \longrightarrow\) d. CC1=CCCC1 e. Cl CC=C(C)CC

Which of the following statements is (are) false? Explain why the statement(s) is (are) false. a. CCOC(=O)CC is a structural isomer of pentanoic acid. is a structural isomer of 2 -methyl-3- b. pentanone. c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) is a structural isomer of 2 -pentanol. d. C=CC(C)O is a structural isomer of 2 -butenal. e. Trimethylamine is a structural isomer of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\).
See all solutions

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

Read Explanation

Making Measurements

Read Explanation

Nuclear Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free