Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 15, Problem 49P
Interpretation Introduction
Interpretation: The pattern of molecular orbitals in cyclonona-
Concept introduction: The inscribed polygon method is helpful to predict whether a compound involves completely filled bonding
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Use the inscribed polygon method to show the pattern of molecular orbitals in cyclonona-1,3,5,7-tetraene, and use it to label its cation, radical, and anion as aromatic, antiaromatic, or not aromatic.
Heteroaromatic Structures
Aromatic compounds which contain non-carbon atoms (e.g., O, N, S) as part of the cyclic conjugated a system are
called heteroaromatics.
the ring OR a lone pair in a p-orbital. Only one p
The heteroatom can be a part of the conjugation as either part of a r bond
orbital from the atom can align to contribute to the aromaticity.
For example, let's look at furan (shown to the right).
How many lone pairs are on the oxygen in this structure?
O 3 lone pairs
O 1 lone pair
O 2 lone pairs
O O lone pairs
How many electrons are in the r bonds?
O 0 electrons
O 4 electrons
O 2 electrons
O 1 electron
O 5 electrons
O 3 electrons
O 6 electrons
To determine, the total number of x electrons to use for the Huckel calculation, you need to determine how many of the
non-bonding electrons on the oxygen are aligned with the x bonds.
Is the red orbital on oxygen aligned with r bonds?
O yes
O no
Is the blue orbital on oxygen aligned with x bonds?
O no
O yes
What is the total number of…
3. Use the inscribed polygon method to show the pattern of molecular orbitals of the following
cyclononatetraenyl cation and anion. Explain their aromaticity.
cyclononatetraenyl
cation
cyclononatetraenyl
anion
Chapter 15 Solutions
Organic Chemistry (6th Edition)
Ch. 15.2 - Prob. 1PCh. 15.2 - Problem 17.2 What orbitals are used to form the...Ch. 15.3 - Prob. 4PCh. 15.3 - Problem-17.5 What is the structure of propofol,...Ch. 15.6 - Prob. 7PCh. 15.8 - Prob. 8PCh. 15.8 - Prob. 11PCh. 15.8 - Prob. 12PCh. 15.8 - Problem 17.16 Rank the following compounds in...Ch. 15.8 - Problem 17.17 Draw the seven resonance structures...
Ch. 15 - 17.23 Name each compound and state how many lines...Ch. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 15 - 17.28 Draw a structure corresponding to each...Ch. 15 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - 17.38
How many electrons does C contain?
How...Ch. 15 - Prob. 36PCh. 15 - 17.40 Explain the observed rate of reactivity of...Ch. 15 - 17.41 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 39PCh. 15 - 17.43 Draw additional resonance structures for...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 17.46 Which compound in each pair is the stronger...Ch. 15 - 17.47 Treatment of indene with forms its...Ch. 15 - Prob. 45PCh. 15 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 15 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - 17.53 How many signals does each compound...Ch. 15 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 15 - 17.55 Propose a structure consistent with each...Ch. 15 - 17.56 Propose a structure consistent with each...Ch. 15 - 17.57 Thymol (molecular formula ) is the major...Ch. 15 - 17.58 You have a sample of a compound of molecular...Ch. 15 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 15 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 15 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 15 - 17.62 Answer the following questions about...Ch. 15 - 17.63 Stanozolol is an anabolic steroid that...Ch. 15 - Prob. 61P
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- Draw a molecular orbital diagram for the pi system of tetrazole (including the piacemen oi iis pi electrons) and provide an analysis of its aromaticity using Hückel's rule denoting whether tetrazole is in fact aromatic, antiaromatic, or nonaromatic. H N° Tetrazole b. Provide a picture of the Highest occupied Molecular Orbital (HOMO) and the Lowest Unnocupied Molecular Orbital (LUMO) of tetrazole depicting the phases of thep orbitals, the bonding, antibonding, and non-bonding interactions.arrow_forwardAside from the multiple ring systems shown in the table, Naphthalene, Anthracene,Phenanthrene Chrysene,Pyrene, and Benzopyrene. Search for 1 multiple ring aromatic compound and list down its properties, sources, and uses or applications.arrow_forwardBorole is a particularly unique heterocycle that has gained considerable attention in recent years for its peculiar reactivity. Draw a molecular orbital diagram for the pi system of borole (including the placement of its pi electrons) and provide an analysis of its aromaticity using Hückel's rule denoting whether borole is in fact aromatic, antiaromatic, or nonaromatic. H Borolearrow_forward
- Explain why the hydroxyl group present in phenol increases the rate of electrophilic aromatic substitution reactions compared with benzene. include a coordinate diagram in the explaination.arrow_forwardExplain the substituent effect on properties of selected molecules such as resonance stability, acidity, acidic properties, basic properties and carbocation stabilityarrow_forwardUse the inscribed polygon method to show the pattern of molecularorbitals in cyclooctatetraene. Indicate the arrangement of electrons in these orbitals forcyclooctatetraene, and explain why cyclooctatetraene is not aromatic.arrow_forward
- Pyrene has been determined experimentally to be aromatic. At first glance, however, its structure appears to break Hückel’s rule. How so? Can you explain why pyrene exhibits aromaticity?Hint: What are the characteristics of the π system on the periphery of the molecule?arrow_forwardFollowing is an example of a type of reaction known as a Diels-Alder reaction 1,3-Pentadiene Ethylene 3-Methylcyclohexene (a racemic mixture) The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is one of the few ways that chemists have to form two new carbon-carbon bonds in a single reaction. Given what you know about the relative strengths of carbon-carbon sigma and pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic? Explain your reasoning.arrow_forwardAside from the multiple ring systems shown in the table, search for 1 multiple ring aromatic compound and list down its properties, sources, and uses or applications.arrow_forward
- Describe the ground-state electron configuration of the cyclopentadienyl cation and radical. Assuming each species is planar, would you expect it to be aromatic or antiaromatic?arrow_forwardWrite a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.arrow_forwardConsider the structure of the cyclopentadienyl anion. cyclopentadienyl anion Complete the Frost circle (i.e., use the inscribed polygon method) for the anion. Classify the aromaticity of the compound. Aromatic Nonaromatic Antiaromatic Energy Answer Bank 1 1.arrow_forward
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