EBK ORGANIC CHEMISTRY
12th Edition
ISBN: 9781119233664
Author: Snyder
Publisher: VST
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Chapter 14, Problem 25P
Interpretation Introduction
Interpretation:
The
Concept introduction:
Annulenes belong to the class of monocyclic compounds and are represented by the structure containing alternating single and double bonds.
For an annulene to be aromatic, the molecule should have
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Chapter 14 Solutions
EBK 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 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 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. 5LGP
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Similar questions
- 7. Which of the following statements regarding the cyclopropenyl anion is correct? and why?a) It is aromatic.b) It is not aromatic.c) It obeys Hückel’s rule.d) It undergoes reactions characteristic of benzene.e) It has a closed shell of 6 pi electrons.arrow_forwardProvide structures for aromatic hydrocarbons that meet the following criteria: a. compound C9H12 that gives only one product C9H1|Br upon halogenation with Br2 in FeBr3 b. compound C10H14 that gives only one compound C10H13B1 upon reaction with Cl2 in FeCl3 c. compound C1,H14 that gives two products C1,H13CI upon reaction with Cl2 in FeCl3arrow_forward3) 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.image iv: colchicine: a highly poisonous alkaloid,obtained from autumn turmeric and used to treat gout.arrow_forward
- Benzopyrene, naphthalene and pyrene are members of these group of aromaticcompounds: *Non-benzenoid aromatic compoundsHeterocyclic aromatic compoundsBenzenoid aromatic compoundsHeteronuclear compoundsWhat type of aromatic compound is pyridine? *Benzenoid aromatic compoundNon-benzenoid aromatic compoundHomonuclear cyclic compoundHeterocyclic aromatic compoundWhat property of aromatic rings prevent the involvement of the conjugated structure toaddition reactions? *Radical stabilizationResonance stabilityInductive effectAromatic effectarrow_forwardDraw a diagram to show the orbitals involved in forming the conjugated six-pi-electron system present in aromatic heterocycle such as pyrolearrow_forwardWhy isn't this compound aromatic? Doesn't it fit the 4n+2 rule where there is 6 pi electrons? Or is it not planar, which is why it is not aromatic?arrow_forward
- Is the following compound aromatic? Explain the reasons for your answer?arrow_forwardA benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forward3. How many electrons does each of the four nitrogen atoms in purine contribute to the aromatic # system? 4. :0 N H 2-1 N N-Phenylsydnone, so-named because it was first studied at the University of Sydney, Australia, behaves like a typical aromatic molecule. Explain, using the Hückel 411 + 2 rule. N : 0: :0 Harrow_forward
- If a molecule contains an aromatic ring, such as a benzene ring, attached to a non-aromatic ring, how does that affect the overall aromaticity of the molecule?arrow_forwardThe compound shown reacts readily with HBr and adds water across at least of one of its double bonds. Why doesn't it behave like Benzene? 1. It is NOT a 4n + 2 system 2. severe steric interactions prevent it from being flat 3. It does NOT have a continous array of p orbitals to overlap 4. There are too many pi bonds to be aromaticarrow_forwardThe 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_forward
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