(a) Interpretation: The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated. 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.

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Answer 1

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Chapter 28, Problem 28.50AP

Interpretation Introduction

(a)

Interpretation:

The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated.

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.

Interpretation Introduction

(b)

Interpretation:

Conversion of product of part (a) into estrone is to be stated.

Concept introduction:

The alcohols (primary and secondary) can be oxidized by using the oxidizing agents like Pyridinium chlorochromate (PCC) and Pyridinium dichromate (PDC).Similarly, demethylation reaction can be accomplished by using HI in heating conditions or by using boron tribromide in dichloromethane.

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1. Refer to the compounds below to answer the following questions: CO₂Et 0 C. H O O₂N-CH2-C-CH3 0 OEt || 111 A. Indicate all the acidic hydrogens in Compounds I through IV. IV B. Indicate which hydrogens in Compound II are the most acidic. Explain your answer C. Choose the most acidic compound from Compounds I - IV. Explain your choice.

Show how you would accomplish the following transformations. More than one step may be required. ow all reagents and all intermediate structures [one ONLY] A. H Br H CH3 NHz CH3 CH3 B. CH3CH2C-Br CH3CH2C-CN CH3 CH3.

Show how you would accomplish the following transformations. More than one step may be required. now all reagents and all intermediate structures [one ONLY] A. H Br H CH3 NHz CH3 CH3 B. CH3CH2C-Br CH3 CH3CH2C-CN CH3

Answer 2

Question

Chapter 28, Problem 28.50AP

Interpretation Introduction

(a)

Interpretation:

The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated.

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.

Interpretation Introduction

(b)

Interpretation:

Conversion of product of part (a) into estrone is to be stated.

Concept introduction:

The alcohols (primary and secondary) can be oxidized by using the oxidizing agents like Pyridinium chlorochromate (PCC) and Pyridinium dichromate (PDC).Similarly, demethylation reaction can be accomplished by using HI in heating conditions or by using boron tribromide in dichloromethane.

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Answer 3

Question

Chapter 28, Problem 28.50AP

Interpretation Introduction

(a)

Interpretation:

The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated.

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.

Interpretation Introduction

(b)

Interpretation:

Conversion of product of part (a) into estrone is to be stated.

Concept introduction:

The alcohols (primary and secondary) can be oxidized by using the oxidizing agents like Pyridinium chlorochromate (PCC) and Pyridinium dichromate (PDC).Similarly, demethylation reaction can be accomplished by using HI in heating conditions or by using boron tribromide in dichloromethane.

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Answer 4

Question

Chapter 28, Problem 28.50AP

Interpretation Introduction

(a)

Interpretation:

The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated.

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.

Interpretation Introduction

(b)

Interpretation:

Conversion of product of part (a) into estrone is to be stated.

Concept introduction:

The alcohols (primary and secondary) can be oxidized by using the oxidizing agents like Pyridinium chlorochromate (PCC) and Pyridinium dichromate (PDC).Similarly, demethylation reaction can be accomplished by using HI in heating conditions or by using boron tribromide in dichloromethane.

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Answer 5

Chapter 28, Problem 28.50AP

Interpretation Introduction

(a)

Interpretation:

The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated.

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.

Interpretation Introduction

(b)

Interpretation:

Conversion of product of part (a) into estrone is to be stated.

Concept introduction:

The alcohols (primary and secondary) can be oxidized by using the oxidizing agents like Pyridinium chlorochromate (PCC) and Pyridinium dichromate (PDC).Similarly, demethylation reaction can be accomplished by using HI in heating conditions or by using boron tribromide in dichloromethane.

Answer 6

Chapter 28, Problem 28.50AP

Interpretation Introduction

(a)

Interpretation:

The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated.

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.

Answer 7

Chapter 28, Problem 28.50AP

Interpretation Introduction

(a)

Interpretation:

The transformation shown in Fig. P28.50, which involves a sequence of two pericyclic reactions, was used as a key step in a synthesis of the sex hormone estrone. The unstable intermediate A is to be identified and the mechanism for both its formation and its subsequent reaction is to be stated.

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.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Conversion of product of part (a) into estrone is to be stated.

Concept introduction:

The alcohols (primary and secondary) can be oxidized by using the oxidizing agents like Pyridinium chlorochromate (PCC) and Pyridinium dichromate (PDC).Similarly, demethylation reaction can be accomplished by using HI in heating conditions or by using boron tribromide in dichloromethane.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Conversion of product of part (a) into estrone is to be stated.

Concept introduction:

The alcohols (primary and secondary) can be oxidized by using the oxidizing agents like Pyridinium chlorochromate (PCC) and Pyridinium dichromate (PDC).Similarly, demethylation reaction can be accomplished by using HI in heating conditions or by using boron tribromide in dichloromethane.

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 schematic mechanism for the formation and subsequent reaction of unstable intermediate A.

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Chapter 28 Solutions