(a) Interpretation: The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted. Concept introduction: Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are; No. of electrons Activation mode Stereochemistry of rotation 4n Thermal Photochemical Con Dis 4n + 2 Thermal Photochemical Dis Con

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Answer 1

Question

Chapter 28, Problem 28.31AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation

4n Thermal
Photochemical Con
Dis

4n + 2 Thermal
Photochemical Dis
Con

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

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Compound A was oxidized with periodic acid to give B, which after acid hydrolysis gave C. Bromine oxidation of C gave D. Suggest structural formulas, including stereochemistry, for compounds B, C, and D.

Deduce the structure of compound C.

(b) Classify the following alcohols in order of increasing ease of acid-catalyzed dehydration.Justify your answers.

Answer 2

Question

Chapter 28, Problem 28.31AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation

4n Thermal
Photochemical Con
Dis

4n + 2 Thermal
Photochemical Dis
Con

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

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Answer 3

Question

Chapter 28, Problem 28.31AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation

4n Thermal
Photochemical Con
Dis

4n + 2 Thermal
Photochemical Dis
Con

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

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Answer 4

Question

Chapter 28, Problem 28.31AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation

4n Thermal
Photochemical Con
Dis

4n + 2 Thermal
Photochemical Dis
Con

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

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Answer 5

Chapter 28, Problem 28.31AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation

4n Thermal
Photochemical Con
Dis

4n + 2 Thermal
Photochemical Dis
Con

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

Answer 6

Chapter 28, Problem 28.31AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation

4n Thermal
Photochemical Con
Dis

4n + 2 Thermal
Photochemical Dis
Con

Answer 7

Chapter 28, Problem 28.31AP

Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation

4n Thermal
Photochemical Con
Dis

4n + 2 Thermal
Photochemical Dis
Con

Answer 8

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 28 - Prob. 28.1P Ch. 28 - Prob. 28.2P Ch. 28 - Prob. 28.3P Ch. 28 - Prob. 28.4P Ch. 28 - Prob. 28.5P Ch. 28 - Prob. 28.6P Ch. 28 - Prob. 28.7P Ch. 28 - Prob. 28.8P Ch. 28 - Prob. 28.9P Ch. 28 - Prob. 28.10P

Solution Summary: The author explains the stereochemistry of compounds B and C in Fig. P28.31. The stereoisomer of A also gives compound C on heating.

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Chapter 28 Solutions

No. of electrons	Activation mode	Stereochemistry of rotation
4n	Thermal Photochemical	Con Dis
4n + 2	Thermal Photochemical	Dis Con