(a) Interpretation: The molecular orbital picture of propa-1, 2-diene is to be drawn. Concept introduction: Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

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Answer 1

Question

Chapter 3, Problem 3.41P

Interpretation Introduction

(a)

Interpretation:

The molecular orbital picture of propa-1, 2-diene is to be drawn.

Concept introduction:

Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

Interpretation Introduction

(b)

Interpretation:

The MO energy diagram of propa-1, 2-diene is to be drawn. The HOMO and LUMO are to be identified.

Concept introduction:

The molecular orbital energy diagram of a molecule is built up by considering the interactions of all the valence shall orbitals from each atom. The total number of MOs produced is the same as the number of interacting AOs.

An end-on overlap of two orbitals produces a pair of MOs of σ symmetry. One of these, the bonding MO, is considerably lower in energy compared to the contributing AOs. The other, an antibonding MO, is higher in energy compared to the contributing AOs by an almost equal amount.

Interactions between p orbitals produces MOs of two types, one pair with a σ symmetry and two pairs with π symmetry. The σ bonding MO is considerably lower in energy than the two π bonding MOs. Conversely, the σ* antibonding MO is considerably higher in energy than the two π* antibonding MOs.

The valence electrons of the contributing atoms are then filled in these MOs in increasing order of energy. The MO of highest energy that contains any electrons is called the highest occupied molecular orbital (HOMO), and the empty MO immediately above it is called the lowest unoccupied molecular orbital (LUMO).

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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…

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Answer 2

Question

Chapter 3, Problem 3.41P

Interpretation Introduction

(a)

Interpretation:

The molecular orbital picture of propa-1, 2-diene is to be drawn.

Concept introduction:

Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

Interpretation Introduction

(b)

Interpretation:

The MO energy diagram of propa-1, 2-diene is to be drawn. The HOMO and LUMO are to be identified.

Concept introduction:

The molecular orbital energy diagram of a molecule is built up by considering the interactions of all the valence shall orbitals from each atom. The total number of MOs produced is the same as the number of interacting AOs.

An end-on overlap of two orbitals produces a pair of MOs of σ symmetry. One of these, the bonding MO, is considerably lower in energy compared to the contributing AOs. The other, an antibonding MO, is higher in energy compared to the contributing AOs by an almost equal amount.

Interactions between p orbitals produces MOs of two types, one pair with a σ symmetry and two pairs with π symmetry. The σ bonding MO is considerably lower in energy than the two π bonding MOs. Conversely, the σ* antibonding MO is considerably higher in energy than the two π* antibonding MOs.

The valence electrons of the contributing atoms are then filled in these MOs in increasing order of energy. The MO of highest energy that contains any electrons is called the highest occupied molecular orbital (HOMO), and the empty MO immediately above it is called the lowest unoccupied molecular orbital (LUMO).

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Answer 3

Question

Chapter 3, Problem 3.41P

Interpretation Introduction

(a)

Interpretation:

The molecular orbital picture of propa-1, 2-diene is to be drawn.

Concept introduction:

Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

Interpretation Introduction

(b)

Interpretation:

The MO energy diagram of propa-1, 2-diene is to be drawn. The HOMO and LUMO are to be identified.

Concept introduction:

The molecular orbital energy diagram of a molecule is built up by considering the interactions of all the valence shall orbitals from each atom. The total number of MOs produced is the same as the number of interacting AOs.

An end-on overlap of two orbitals produces a pair of MOs of σ symmetry. One of these, the bonding MO, is considerably lower in energy compared to the contributing AOs. The other, an antibonding MO, is higher in energy compared to the contributing AOs by an almost equal amount.

Interactions between p orbitals produces MOs of two types, one pair with a σ symmetry and two pairs with π symmetry. The σ bonding MO is considerably lower in energy than the two π bonding MOs. Conversely, the σ* antibonding MO is considerably higher in energy than the two π* antibonding MOs.

The valence electrons of the contributing atoms are then filled in these MOs in increasing order of energy. The MO of highest energy that contains any electrons is called the highest occupied molecular orbital (HOMO), and the empty MO immediately above it is called the lowest unoccupied molecular orbital (LUMO).

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Answer 4

Question

Chapter 3, Problem 3.41P

Interpretation Introduction

(a)

Interpretation:

The molecular orbital picture of propa-1, 2-diene is to be drawn.

Concept introduction:

Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

Interpretation Introduction

(b)

Interpretation:

The MO energy diagram of propa-1, 2-diene is to be drawn. The HOMO and LUMO are to be identified.

Concept introduction:

The molecular orbital energy diagram of a molecule is built up by considering the interactions of all the valence shall orbitals from each atom. The total number of MOs produced is the same as the number of interacting AOs.

An end-on overlap of two orbitals produces a pair of MOs of σ symmetry. One of these, the bonding MO, is considerably lower in energy compared to the contributing AOs. The other, an antibonding MO, is higher in energy compared to the contributing AOs by an almost equal amount.

Interactions between p orbitals produces MOs of two types, one pair with a σ symmetry and two pairs with π symmetry. The σ bonding MO is considerably lower in energy than the two π bonding MOs. Conversely, the σ* antibonding MO is considerably higher in energy than the two π* antibonding MOs.

The valence electrons of the contributing atoms are then filled in these MOs in increasing order of energy. The MO of highest energy that contains any electrons is called the highest occupied molecular orbital (HOMO), and the empty MO immediately above it is called the lowest unoccupied molecular orbital (LUMO).

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Answer 5

Chapter 3, Problem 3.41P

Interpretation Introduction

(a)

Interpretation:

The molecular orbital picture of propa-1, 2-diene is to be drawn.

Concept introduction:

Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

Interpretation Introduction

(b)

Interpretation:

The MO energy diagram of propa-1, 2-diene is to be drawn. The HOMO and LUMO are to be identified.

Concept introduction:

The molecular orbital energy diagram of a molecule is built up by considering the interactions of all the valence shall orbitals from each atom. The total number of MOs produced is the same as the number of interacting AOs.

An end-on overlap of two orbitals produces a pair of MOs of σ symmetry. One of these, the bonding MO, is considerably lower in energy compared to the contributing AOs. The other, an antibonding MO, is higher in energy compared to the contributing AOs by an almost equal amount.

Interactions between p orbitals produces MOs of two types, one pair with a σ symmetry and two pairs with π symmetry. The σ bonding MO is considerably lower in energy than the two π bonding MOs. Conversely, the σ* antibonding MO is considerably higher in energy than the two π* antibonding MOs.

The valence electrons of the contributing atoms are then filled in these MOs in increasing order of energy. The MO of highest energy that contains any electrons is called the highest occupied molecular orbital (HOMO), and the empty MO immediately above it is called the lowest unoccupied molecular orbital (LUMO).

Answer 6

Chapter 3, Problem 3.41P

Interpretation Introduction

(a)

Interpretation:

The molecular orbital picture of propa-1, 2-diene is to be drawn.

Concept introduction:

Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

Answer 7

Chapter 3, Problem 3.41P

Interpretation Introduction

(a)

Interpretation:

The molecular orbital picture of propa-1, 2-diene is to be drawn.

Concept introduction:

Orbital picture of a molecule can be built up by first determining which orbitals will overlap and interact effectively. These are generally the orbitals from the valence shell of the atoms forming the bonds; mostly s and p orbitals. The orbital that will overlap end-on and the ones that overlap sideways are then determined on the basis of the electron geometry of the atoms. End on overlap leads to σ interactions while sideways overlap leads to π interactions.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The MO energy diagram of propa-1, 2-diene is to be drawn. The HOMO and LUMO are to be identified.

Concept introduction:

The molecular orbital energy diagram of a molecule is built up by considering the interactions of all the valence shall orbitals from each atom. The total number of MOs produced is the same as the number of interacting AOs.

An end-on overlap of two orbitals produces a pair of MOs of σ symmetry. One of these, the bonding MO, is considerably lower in energy compared to the contributing AOs. The other, an antibonding MO, is higher in energy compared to the contributing AOs by an almost equal amount.

Interactions between p orbitals produces MOs of two types, one pair with a σ symmetry and two pairs with π symmetry. The σ bonding MO is considerably lower in energy than the two π bonding MOs. Conversely, the σ* antibonding MO is considerably higher in energy than the two π* antibonding MOs.

The valence electrons of the contributing atoms are then filled in these MOs in increasing order of energy. The MO of highest energy that contains any electrons is called the highest occupied molecular orbital (HOMO), and the empty MO immediately above it is called the lowest unoccupied molecular orbital (LUMO).

Answer 9

Interpretation Introduction

(b)

Interpretation:

The MO energy diagram of propa-1, 2-diene is to be drawn. The HOMO and LUMO are to be identified.

Concept introduction:

The molecular orbital energy diagram of a molecule is built up by considering the interactions of all the valence shall orbitals from each atom. The total number of MOs produced is the same as the number of interacting AOs.

An end-on overlap of two orbitals produces a pair of MOs of σ symmetry. One of these, the bonding MO, is considerably lower in energy compared to the contributing AOs. The other, an antibonding MO, is higher in energy compared to the contributing AOs by an almost equal amount.

Interactions between p orbitals produces MOs of two types, one pair with a σ symmetry and two pairs with π symmetry. The σ bonding MO is considerably lower in energy than the two π bonding MOs. Conversely, the σ* antibonding MO is considerably higher in energy than the two π* antibonding MOs.

The valence electrons of the contributing atoms are then filled in these MOs in increasing order of energy. The MO of highest energy that contains any electrons is called the highest occupied molecular orbital (HOMO), and the empty MO immediately above it is called the lowest unoccupied molecular orbital (LUMO).

Answer 10

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Answer 12

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Answer 13

Ch. 3 - Prob. 3.1P Ch. 3 - Prob. 3.2P Ch. 3 - Prob. 3.3P Ch. 3 - Prob. 3.4P Ch. 3 - Prob. 3.5P Ch. 3 - Prob. 3.6P Ch. 3 - Prob. 3.7P Ch. 3 - Prob. 3.8P Ch. 3 - Prob. 3.9P Ch. 3 - Prob. 3.10P

Solution Summary: The author explains how the molecular orbital picture of propa-1, 2-diene can be drawn by determining which orbitals will overlap and interact effectively.

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