An energy diagram for the three molecular orbitals of the cyclopropenyl system is to be drawn. How these three molecular orbitals are occupied in the cyclopropenyl anion, cation and radical is to be indicated. Which among the three is aromatic is also to be stated. Concept introduction: The numberof molecular orbitals formed is equal to the number of orbitals overlapping. The available orbitals are filled by the electrons in the increasing order of their energies.Each moleclar orbital can accommodate two electrons with opposite spin. Electrons occupy the orbitals individually first before they get paired in the same orbital. The cyclopropenyl cation has two electrons to be filled in molecular orbitals. The cyclopropenyl radical has three electrons to be filled in molecular orbitals. The cycloproenyl anion has four electrons to be filled in molecular orbitals. To draw: The relative energy levels of the three Ï€ molecular orbitals of the cyclopropenyl cation, radical and anion. To indicate: How the three Ï€ molecular orbitals are filled in cyclopropenyl cation, radical and anion. To state: Which of these three are aromatic.

Question

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?

Answer 1

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 30AP

Interpretation Introduction

Interpretation:

An energy diagram for the three molecular orbitals of the cyclopropenyl system is to be drawn. How these three molecular orbitals are occupied in the cyclopropenyl anion, cation and radical is to be indicated. Which among the three is aromatic is also to be stated.

Concept introduction:

The numberof molecular orbitals formed is equal to the number of orbitals overlapping. The available orbitals are filled by the electrons in the increasing order of their energies.Each moleclar orbital can accommodate two electrons with opposite spin. Electrons occupy the orbitals individually first before they get paired in the same orbital.

The cyclopropenyl cation has two electrons to be filled in molecular orbitals.

The cyclopropenyl radical has three electrons to be filled in molecular orbitals.

The cycloproenyl anion has four electrons to be filled in molecular orbitals.

To draw:

The relative energy levels of the three Ï€ molecular orbitals of the cyclopropenyl cation, radical and anion.

To indicate:

How the three Ï€ molecular orbitals are filled in cyclopropenyl cation, radical and anion.

To state:

Which of these three are aromatic.

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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?

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…

Why is benzene less reactive than hexane in terms of stability of free radicals?

Answer 2

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 30AP

Interpretation Introduction

Interpretation:

An energy diagram for the three molecular orbitals of the cyclopropenyl system is to be drawn. How these three molecular orbitals are occupied in the cyclopropenyl anion, cation and radical is to be indicated. Which among the three is aromatic is also to be stated.

Concept introduction:

The numberof molecular orbitals formed is equal to the number of orbitals overlapping. The available orbitals are filled by the electrons in the increasing order of their energies.Each moleclar orbital can accommodate two electrons with opposite spin. Electrons occupy the orbitals individually first before they get paired in the same orbital.

The cyclopropenyl cation has two electrons to be filled in molecular orbitals.

The cyclopropenyl radical has three electrons to be filled in molecular orbitals.

The cycloproenyl anion has four electrons to be filled in molecular orbitals.

To draw:

The relative energy levels of the three Ï€ molecular orbitals of the cyclopropenyl cation, radical and anion.

To indicate:

How the three Ï€ molecular orbitals are filled in cyclopropenyl cation, radical and anion.

To state:

Which of these three are aromatic.

Expert Solution & Answer

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Check out sample textbook solution

Answer 3

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 30AP

Interpretation Introduction

Interpretation:

An energy diagram for the three molecular orbitals of the cyclopropenyl system is to be drawn. How these three molecular orbitals are occupied in the cyclopropenyl anion, cation and radical is to be indicated. Which among the three is aromatic is also to be stated.

Concept introduction:

The numberof molecular orbitals formed is equal to the number of orbitals overlapping. The available orbitals are filled by the electrons in the increasing order of their energies.Each moleclar orbital can accommodate two electrons with opposite spin. Electrons occupy the orbitals individually first before they get paired in the same orbital.

The cyclopropenyl cation has two electrons to be filled in molecular orbitals.

The cyclopropenyl radical has three electrons to be filled in molecular orbitals.

The cycloproenyl anion has four electrons to be filled in molecular orbitals.

To draw:

The relative energy levels of the three Ï€ molecular orbitals of the cyclopropenyl cation, radical and anion.

To indicate:

How the three Ï€ molecular orbitals are filled in cyclopropenyl cation, radical and anion.

To state:

Which of these three are aromatic.

Expert Solution & Answer

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See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 30AP

Interpretation Introduction