Q3Draw the structure of the cyclopentadienyl cation (C5H5*). Sketch a Frost diagram of the T-orbitalsystem of the cyclopentadienyl cation. Clearly illustrate bonding, non-bonding and antibondingenergy levels, and show electron occupation of orbitals for the ground state. State whether thecation is aromatic or not and explain your answer.

Answered: Q3 Draw the structure of the…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter15: Benzene And Aromaticity

Section15.SE: Something Extra

Problem 17VC: Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon (Î¼ = 1.0...

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The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpairedelectron onto three carbon atoms.(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atomsshare the positive charge? Does this picture agree with the resonance picture?(h) Add an…
The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?
Sketch the ultraviolet absorption spectrum of 1,3-Butadiene, matching peaks to electronic transitions. show that four isolated p orbital on carbon atoms combine to form pi orbital
Aromatic compounds must have a p orbital on every atom in the ring. Define this ?
The bonding between the carbon and oxygen in a ketone can be described as C(sp2)-0(sp²), o-bond and C(p)-O(p), л-bond. How would you describe the bonding between carbon and oxygen in a ketene? Sketch the orbitals used to make the bonds in the ketene. H a ketene
Explain how covalent bonds are formed in each of the following compounds in terms of orbital hybridisation and overlap of orbitals (i) Ethene, C2H4 (ii) Ethyne, C2H2
What is the major difference between an antiaromatic and aromatic compound? Antiaromatic compounds have at least one sp³ hybridized atom in the ring. Antiaromatic compounds are not conjugated. Only aromatic compounds have 4n+ 2 pi electrons. The structure must be cyclic for aromatic but not antiaromatic compounds. Aromatic, not Antiaromatic compounds, are planar.
The unsaturation number or degree of unsaturation (U) can be used to determine the number of rings and multiple bonds in a compound from its molecular formula. Given a structure, you can determine the number of hydrogens without having to count them explicitly. Consider three compounds and their degree of unsaturation. (a) A compound A has the molecular formula C7H13ClN2OC7⁢H13⁢ClN2O. How many rings and/or π bonds does it contain?
(a) How many π molecular orbitals are present in deca-1,3,5,7,9-pentaene (CH2 = CH – OH = OH – CH = CH – OH = OH – CH = CH2)? (b) How many are bonding MOs and how many are antibonding MOs? (c) How many nodes are present in ψ1? (d) How many nodes are present in ψ10*
Explain the Carbon-Carbon σ Bond Length in Buta- 1,3-diene ?
Specify whether the two structures are resonance contributors to the same resonance hybrid. Be sure to explain your reasoning. If yes, be sure to specify which is preferred and why. H2C=NH2
(b) The structure of heptalene (2E) is shown below. Answer the following questions: (i) Is heptalene aromatic, non-aromatic, or anti-aromatic? (ii) 2E can be readily protonated to form a more stable species. Draw the structure of the protonated 2E and explain the stability. heptalene (2E)

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