Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.52P
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.
Use the inscribed polygon method to show the pattern of molecularorbitals in cyclooctatetraene.
Classify the dianion of cyclooctatetraene as aromatic, antiaromatic, ornot aromatic, and explain why this is so.
2- Apply the polygon-and-circle method to the cyclopentadienyl cation and explain whether it would
be aromatic or not.
Cyclopentadienyl
cation
Chapter 17 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Ch. 17 - Prob. 17.1PCh. 17 - Problem 17.2 What orbitals are used to form the...Ch. 17 - Problem-17.3. Give the IUPAC name for each...Ch. 17 - Prob. 17.4PCh. 17 - Problem-17.5 What is the structure of propofol,...Ch. 17 - Problem 17.6 What is the structure of a compound...Ch. 17 - Problem 17.7 How many NMR signals does each...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.34PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - Prob. 17.37PCh. 17 - 17.38
How many electrons does C contain?
How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.64PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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- Fill the blank space. Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound containing a phenol group with antioxidant properties is: ---------.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_forwardCyclic hydrocarbons with alternating double and single bonds throughout are called annulenes. A bracketed number is used to indicate the number of carbons in the ring. Which of the following annulenes are aromatic?arrow_forward
- The heterocyclopentadienes listed contain more than one heteroatom. For each molecule, identify the orbitals occupied by each lone pair and determine whether the molecule is aromatic. For the sulfur and oxygen, two sets of lone pairs will each be in a different orbital, so place 2 orbitals in the box. N. 4 pyrazole Aromatic or not? P isoxazole pyrazole imidazole thiazole H imidazole Answer Bank non-aromatic aromatic Which heterocycles are more basic than pyrrole? sp² thiazole :0: isoxazolearrow_forwardThe following is an example of a hetero Diels-Alder reaction, because a noncarbon atom (in this case, an N atom) is involved in bond formation and bond breaking. Draw the curved arrows necessary to account for this transformation. OCH3 OCH3 + N- Hydroquinone, benzene, 25 °C, 90 min 86%arrow_forwardWhich is more stable - a phenyl radical, [C6H5]•, or a benzyl radical, [C6H5CH2]• - and why?arrow_forward
- Use 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_forwardNonearrow_forward(a) Thiamin, or vitamin B, contains a positively charged five-membered nitrogen-sulfur heterocycle called a thiazolium ring. Determine if the pyrimidine ring and thiazolium ring are aromatic or not, and explain your answer. H₂C منایا؟ pyrimidine ring NH₂ thiazolium ring CH3 OHarrow_forward
- This is a Diels-Alder reaction between cyclopentadiene and maleic anhydride (endo and exo products). For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.arrow_forwardArrange them in the increasing order of stability by applying the rules of aromaticity for the following compounds individually and justify your answer. Give out the necessar 9 CH3 NH₂ CH3 CH₂ CH3arrow_forwardCyclopentadienyl anion (shown) has the following characteristic. O it is an anion with six π electrons, meeting the Hückel rule for aromaticity O it is not aromatic because it has only four electrons and the tetrahedral carbon prevents cyclic conjugation O it is an anion with six electrons, meeting the Hückel rule for anti-aromaticity O it is an anion with four electrons, meeting the Hückel rule for aromaticityarrow_forward
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