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Some of the following compounds show aromatic properties,

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 35SP Chapter 16

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 35SP

Some of the following compounds show aromatic properties, and others do not.

1. Predict which ones are likely to be aromatic, and explain why they are aromatic.

2. Predict which nitrogen atoms are more basic than water and which are less basic.

Step-by-Step Solution:
Step 1 of 3

Solution 35SP

  1. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic.
  2. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic.
  3. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic.
  4. The resonance structure on the right does have a stable oxygen, but it only has 4 electrons. As a result, this compound is not aromatic.
  5. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic.
  6. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic. Because the nitrogen is positively charged, it doesn’t have a lone pair of electrons available for use as a base, so it’s going to be less basic than water.
  7. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic. Because the nitrogen is positively charged, it doesn’t have a lone pair of electrons available for use as a base, so it’s going to be less basic than water.
  8. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic. Because the nitrogen at the top is positively charged, it doesn’t have a lone pair of electrons available for use as a base, so it’s going to be less basic than water. This molecule is not aromatic because it is not planar; the carbon at the bottom of the ring also breaks the conjugation. Although both nitrogens have available lone pairs and are therefore basic, the top nitrogen’s electrons lie in conjugation with the two alkenes and so this nitrogen is slightly less basic than the other nitrogen in the ring.
  9. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic. Because the nitrogen at the bottom is positively charged, it doesn’t have a lone pair of electrons available for use as a base, so it’s going to be less basic than water. The nitrogens on the side and at the top have a free lone pair that is not part of the delocalized  system, and so that nitrogen is going to be more basic than water.
  10. This molecule has a delocalized / conjugated  system, a planar ring, and 6 delocalized electrons. It is aromatic. Because the nitrogen at the bottom is positively charged, it doesn’t have a lone pair of electrons available for use as a base, so it’s going to be less basic than water.
  11. Both the nitrogen and the oxygen are  hybridized, meaning the  system of this compound has 8 electrons. It therefore does not meet the requirements for aromaticity. Because the nitrogen’s lone pair of electrons is not needed for the formation of the delocalized system, it will be more basic than water.
  12. This molecule is not aromatic. In order to form a delocalized system of  electrons, the nitrogen would have to participate which would bring the total number of  electrons up to eight. This does not match the requirements for aromaticity. Since the nitrogen atoms are not needed to reach aromaticity, they are free to act as a base and so the nitrogen will be more basic than water.
  13. This molecule has a delocalized / conjugated  system (empty p orbital at the carbocation), a planar ring, and 6 delocalized  electrons. It is aromatic.
  14. This molecule has a delocalized / conjugated    system (empty p orbital at the carbocation), a planar ring, and 6 delocalized  electrons. It is aromatic.
  15. This material appears to meet all the requirements for aromaticity. However, the oxygen atom lacks a complete octet. Oxygen is an electronegative element and so it’s quite unstable with a positive charge. As a result, this particular resonance structure is only a very minor contributor to the overall resonance hybrid. As a result, this material does not behave in an aromatic fashion

Step 2 of 3

Chapter 16, Problem 35SP is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This full solution covers the following key subjects: aromatic, predict, basic, nitrogen, explain. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. Since the solution to 35SP from 16 chapter was answered, more than 649 students have viewed the full step-by-step answer. The answer to “?Some of the following compounds show aromatic properties, and others do not. 1. Predict which ones are likely to be aromatic, and explain why they are aromatic. 2. Predict which nitrogen atoms are more basic than water and which are less basic.” is broken down into a number of easy to follow steps, and 42 words. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The full step-by-step solution to problem: 35SP from chapter: 16 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM.

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Some of the following compounds show aromatic properties,