MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric. Concept introduction: Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed. Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals. Molecular orbitals can be constructed from linear combination of atomic orbitals. Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals. Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact. Antibonding orbitals have higher energy than the bonding molecular orbitals. Ground state and and exited states are the positions with lower and higher energy respectively. HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital. LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital. If the lobes at the ends of the MO are in phase, then the MO is symmetric. If the two lobes are out phase then the MO is antisymmetric. Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions. Woodward – Hoffmann rules for Electrocyclic reactions are listed below Number of conjugated Π bonds Reaction conditions Allowed mode of rong closure Even number Thermal Conrotatory Photochemical Disrotatory Odd number Thermal Disrotatory Photochemical Conrotatory

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Answer 1

Question

Chapter 28.3, Problem 5P

(a)

Interpretation Introduction

Interpretation: MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric.

Concept introduction:

Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals.

Molecular orbitals can be constructed from linear combination of atomic orbitals.

Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals.

Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact.

Antibonding orbitals have higher energy than the bonding molecular orbitals.

Ground state and and exited states are the positions with lower and higher energy respectively.

HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital.

LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital.

If the lobes at the ends of the MO are in phase, then the MO is symmetric.

If the two lobes are out phase then the MO is antisymmetric.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

(b)

Interpretation Introduction

Interpretation: The validity of Woodward – Hoffmann rule for an electrocyclic reaction has to be checked using the MOs of given systems.

Concept introduction:

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

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The pKa of cyclopentane is > 60, which is about what is expected for a hydrogen that is bonded to an sp3 carbon. Explain why cyclopentadiene is a much stronger acid (pKa of 15) even though it too involves the loss of a proton from an sp3 carbon.

Is the following true or false? To catalyse a Diels-Alder reaction a common approach involves the use of a Lewis acid capable of lowering the LUMO of the dienophile.

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Answer 2

Question

Chapter 28.3, Problem 5P

(a)

Interpretation Introduction

Interpretation: MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric.

Concept introduction:

Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals.

Molecular orbitals can be constructed from linear combination of atomic orbitals.

Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals.

Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact.

Antibonding orbitals have higher energy than the bonding molecular orbitals.

Ground state and and exited states are the positions with lower and higher energy respectively.

HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital.

LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital.

If the lobes at the ends of the MO are in phase, then the MO is symmetric.

If the two lobes are out phase then the MO is antisymmetric.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

(b)

Interpretation Introduction

Interpretation: The validity of Woodward – Hoffmann rule for an electrocyclic reaction has to be checked using the MOs of given systems.

Concept introduction:

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Expert Solution & Answer

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Check out a sample textbook solution

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Answer 3

Question

Chapter 28.3, Problem 5P

(a)

Interpretation Introduction

Interpretation: MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric.

Concept introduction:

Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals.

Molecular orbitals can be constructed from linear combination of atomic orbitals.

Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals.

Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact.

Antibonding orbitals have higher energy than the bonding molecular orbitals.

Ground state and and exited states are the positions with lower and higher energy respectively.

HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital.

LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital.

If the lobes at the ends of the MO are in phase, then the MO is symmetric.

If the two lobes are out phase then the MO is antisymmetric.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

(b)

Interpretation Introduction

Interpretation: The validity of Woodward – Hoffmann rule for an electrocyclic reaction has to be checked using the MOs of given systems.

Concept introduction:

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Expert Solution & Answer

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Check out a sample textbook solution

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Answer 4

Question

Chapter 28.3, Problem 5P

(a)

Interpretation Introduction

Interpretation: MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric.

Concept introduction:

Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals.

Molecular orbitals can be constructed from linear combination of atomic orbitals.

Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals.

Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact.

Antibonding orbitals have higher energy than the bonding molecular orbitals.

Ground state and and exited states are the positions with lower and higher energy respectively.

HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital.

LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital.

If the lobes at the ends of the MO are in phase, then the MO is symmetric.

If the two lobes are out phase then the MO is antisymmetric.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

(b)

Interpretation Introduction

Interpretation: The validity of Woodward – Hoffmann rule for an electrocyclic reaction has to be checked using the MOs of given systems.

Concept introduction:

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 28.3, Problem 5P

(a)

Interpretation Introduction

Interpretation: MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric.

Concept introduction:

Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals.

Molecular orbitals can be constructed from linear combination of atomic orbitals.

Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals.

Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact.

Antibonding orbitals have higher energy than the bonding molecular orbitals.

Ground state and and exited states are the positions with lower and higher energy respectively.

HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital.

LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital.

If the lobes at the ends of the MO are in phase, then the MO is symmetric.

If the two lobes are out phase then the MO is antisymmetric.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

(b)

Interpretation Introduction

Interpretation: The validity of Woodward – Hoffmann rule for an electrocyclic reaction has to be checked using the MOs of given systems.

Concept introduction:

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Answer 6

Chapter 28.3, Problem 5P

(a)

Interpretation Introduction

Interpretation: MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric.

Concept introduction:

Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals.

Molecular orbitals can be constructed from linear combination of atomic orbitals.

Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals.

Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact.

Antibonding orbitals have higher energy than the bonding molecular orbitals.

Ground state and and exited states are the positions with lower and higher energy respectively.

HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital.

LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital.

If the lobes at the ends of the MO are in phase, then the MO is symmetric.

If the two lobes are out phase then the MO is antisymmetric.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Answer 7

Chapter 28.3, Problem 5P

(a)

Interpretation Introduction

Interpretation: MOs for the given conjugated systems has to be drawn and the HOMO has to be predicted as symmetric or antisymmetric.

Concept introduction:

Conjugated system: A system of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

Molecular orbital theory suggests that atomic orbitals of different atoms combines to create molecular orbitals.

Molecular orbitals can be constructed from linear combination of atomic orbitals.

Bonding orbotals are formed by the additive combination of atomic orbitals and the antibonding orbitals are formed by the substractive combination of atomic orbitals.

Antibonding orbital is a molecular orbital that results when two parallel atomic orbitals with opposite phases interact.

Antibonding orbitals have higher energy than the bonding molecular orbitals.

Ground state and and exited states are the positions with lower and higher energy respectively.

HOMO is a molecular orbital which is the abbrevation of Highest Occupied Molecular Orbital.

LUMO is also a molecular orbital which is the short form of Lowest Unoccupied Molecular Orbital.

If the lobes at the ends of the MO are in phase, then the MO is symmetric.

If the two lobes are out phase then the MO is antisymmetric.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Answer 8

(b)

Interpretation Introduction

Interpretation: The validity of Woodward – Hoffmann rule for an electrocyclic reaction has to be checked using the MOs of given systems.

Concept introduction:

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Answer 9

(b)

Interpretation Introduction

Interpretation: The validity of Woodward – Hoffmann rule for an electrocyclic reaction has to be checked using the MOs of given systems.

Concept introduction:

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for Electrocyclic reactions are listed below

Number of conjugated Π bondsReaction conditionsAllowed mode of rong closureEven numberThermalConrotatoryPhotochemicalDisrotatoryOdd numberThermalDisrotatoryPhotochemicalConrotatory

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 28.1 - Prob. 1P Ch. 28.2 - Prob. 2P Ch. 28.2 - Prob. 3P Ch. 28.2 - Give a molecular orbital description for each of...Ch. 28.3 - Prob. 5P Ch. 28.3 - Prob. 6P Ch. 28.3 - Prob. 7P Ch. 28.3 - Prob. 8P Ch. 28.4 - Prob. 9P Ch. 28.4 - Prob. 11P

Solution Summary: The author explains that a conjugated system is composed of connected p-orbitals with delocalized electrons with alternating single and multiple bonds and the compound may be cyclic, linear or mixed.

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Chapter 28 Solutions