(a) Interpretation: The given compound is to be identified as aromatic, antiaromatic, or nonaromatic. Concept introduction: Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity. A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π -electrons in the cyclic system is 4n+2 , where n = 0, 1, 2, ... The species is antiaromatic if the number of π -electrons in the cyclic system is 4n , where n = 0, 1, 2, ... All other species are nonaromatic. For the π system of MOs constructed from p orbitals, the ring must be planar.

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Answer 1

Question

Chapter 14, Problem 14.25P

Interpretation Introduction

(a)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(b)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(c)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

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2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**

11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

Answer 2

Question

Chapter 14, Problem 14.25P

Interpretation Introduction

(a)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(b)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(c)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

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Answer 3

Question

Chapter 14, Problem 14.25P

Interpretation Introduction

(a)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(b)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(c)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

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Answer 4

Question

Chapter 14, Problem 14.25P

Interpretation Introduction

(a)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(b)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(c)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

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See solution

Answer 5

Chapter 14, Problem 14.25P

Interpretation Introduction

(a)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(b)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Interpretation Introduction

(c)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Answer 6

Chapter 14, Problem 14.25P

Interpretation Introduction

(a)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Answer 7

Chapter 14, Problem 14.25P

Interpretation Introduction

(a)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses an π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The given compound is to be identified as aromatic, antiaromatic or nonaromatic.

Concept introduction:

Cyclic compounds with a conjugated π system can be classified on the basis of Huckel’s rules for aromaticity.

A species that possesses a π system that is fully conjugated around a ring is aromatic if the number of π-electrons in the cyclic system is 4n+2, where n = 0, 1, 2, ...

The species is antiaromatic if the number of π-electrons in the cyclic system is 4n, where n = 0, 1, 2, ...

All other species are nonaromatic.

For the π system of MOs constructed from p orbitals, the ring must be planar.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 14 - Prob. 14.1P Ch. 14 - Prob. 14.2P Ch. 14 - Prob. 14.3P Ch. 14 - Prob. 14.4P Ch. 14 - Prob. 14.5P Ch. 14 - Prob. 14.6P Ch. 14 - Prob. 14.7P Ch. 14 - Prob. 14.8P Ch. 14 - Prob. 14.9P Ch. 14 - Prob. 14.10P

Solution Summary: The author explains that the structure of the given compound is based on Huckel's rules for aromaticity. The lone pairs on the two nitrogen atoms are not involved in the conjugation.

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Chapter 14 Solutions