Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 14, Problem 23P
Interpretation Introduction
Interpretation:
The aromatic nature of pentalene and heptalene needs to be explained on the basis of
Concept introduction:
In accordance to the Huckel’s rule,
Aromatic compounds contain conjugated pi bonds.
All the atoms in the ring have an unhybridized
Antiaromatic compounds contain
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Cyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three ℼ-electron
3) In the mid-1930s, the German theoretical chemist Erich Hückel developed a rule that dealt with the aromaticity of various compounds, which became known as the Hückel Rule. Which (parts) of the compounds listed below are aromatic? Justify your answer based on Hückel's rule. You can treat the rings separately or together as you wish.
Which of the following compounds are aromatic and anti-aromatic? Give
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Chapter 14 Solutions
Organic Chemistry
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - A compound (N) with the molecular formula C9H10O...Ch. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 38PCh. 14 - Prob. 39PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 42PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGPCh. 14 - Prob. 1QCh. 14 - Which is the correct name of the compound shown?...Ch. 14 - Prob. 3QCh. 14 - Prob. 4QCh. 14 - Give the structure of a compound with the formula...Ch. 14 - Prob. 6Q
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- Cyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three π-electrons?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_forwardAcridine is a heterocyclic aromatic compound obtained from coal tar that is used in the synthesis of dyes. The molecular formula of acridine is C13H9N, and its ring system is analogous to that of anthracene except that one CH group has been replaced by N. The two most stable resonance structures of acridine are equivalent to each other, and both contain a pyridine-like structural unit. Write a structural formula for acridine.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_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_forwardAromatic heterocyclic chemistry: State whether the following drugs are aromatic heterocycles and if they follow the 4 aromaticity rules (unsaturation, (4n + 2)pi electrons, cyclic and flat/planar), NAME ANY HETEROCYCLES. Draw the structure of the core of any aromatic heterocycles in the drug. Riociguat, Imatinib, Clopidogrel, Glatiramer acetate, Axitinibarrow_forward
- 11. See Fundamentals P167 for Figure 5.6 Use Figure 5.6 to rank the compounds in each of the following groups in order of their reactivity toward electrophilic aromatic substitution: (a) Nitrobenzene, phenol (hydroxybenzene), toluene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, aniline (aminobenzene)arrow_forwardAromatic compounds also known as arenes or aromatic are chemical compounds that contain conjugated planar ring system with delocalized pi electron clouds instead of discrete alternating single and double bond. One of the precursor to produce aromatic compounds is arenediazonium.Critize this statementarrow_forwardDraw 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_forward
- To be aromatic, a molecule must have 4n + 2 πs electrons and must have a planar, monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. Explain.arrow_forwardThere are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppmarrow_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_forward
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