Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 28, Problem 28.5P
Interpretation Introduction

(a)

Interpretation:

The reason as to why the unpaired electron in the allyl radical is delocalized over C1, C3 positions with the help of resonance structures is to be stated.

Concept introduction:

Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure.

Interpretation Introduction

(b)

Interpretation:

The reason as to why the unpaired electron in the allyl radical is delocalized over C1, C3 positions with the help of molecular orbital arguments is to be stated.

Concept introduction:

The molecular orbital is a combination of two atomic orbitals. It is used to represent the regions in a molecule where the electron is likely to be present in an orbital. It represents the wave-like nature of an electron in a molecule.

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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
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.(
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