ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
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 cyclonona-1,3,5,7-tetraene, and use it to label its cation,radical, and anion as aromatic, antiaromatic, or not aromatic.
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 17 Solutions
ORGANIC CHEMISTRY
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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- 3) Outline an acceptable step by step mechanism for the Nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine. Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge.arrow_forwardDo not handwriting solution.arrow_forwardThe compound below is treated with N- bromosuccinimide (NBS) in the presence of light. 어 Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Separate resonance structures using the → symbol from the drop-down menu. • Include all valence radical electrons in your answer.arrow_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_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_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
- 11:38 1. Is the following compound aromatic or not? Motivate your answer by using Huckel's rule." 2. Show a reaction scheme with all the reactants and reagents of the nitration reaction of bromobenzene and show the major products(s), with valid reasons motivate why the positioning of the two constituents' favour ortho, para and/or meta positioning Add a caption... > Status (Custom) +arrow_forwardImagine that you used isoprene as diene – in that case you don’t have to worry about assigning endo vs exo. Draw the "endo" and "exo" products of the Diels-Alder reaction between isoprene and maleic anhydride, and explain why the distinction is irrelevant here.arrow_forwardThe compound below is treated with N-bromosuccinimide (NBS) in the presence of light. z Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Separate resonance structures using the symbol from the drop-down menu. • Include all valence radical electrons in your answer. ? 24 On []arrow_forward
- Compounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe O C8H12O2 R C8H12O2 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. Using curly arrows, draw the mechanism for the reaction of P and Q to form the dominant regioisomer you have predicted in your answer to part (ii) above.arrow_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_forwardwhat aromatic annulene has the same number of bond molecular orbital as the hypothetical all cis (20) annulenearrow_forward
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