(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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Experiment 1 Data Table 1: Conservation of Mass - Initial Mass Data Table 1 Data Table 2 Data Table 3 Data Table 4 Panel 1 Photo 1 Data Table 5 Reaction Mass of test tube and 5.0% HC₂H₂O2 (g) # (A) (B) Mass of NaHCO, (g) Mass of balloon and NaHCO, (g) (C) 0.10 1 0829 14.38g 0.20 2 0.929 14.29g 0.35 1.00g 3 14.25g 0.50 1.14g 14.29 Experiment 1 Data Table 2: Moles of HC2H3O2 Reaction Volume of Mass of Moles of HC₂H₂O₂ 5.0% Vinegar (g) (ML) 5.0 0.25 0042 mol 2 5.0 0.25 0042 mol 3 5.0 0.25 0042 mol 5.0 0.25 0042 mol Experiment 1 Data Table 3: Moles of NaHCO3 Reaction Mass of NaHCO (g) 10g 20g 35g 50g Experiment 1 Data Table 4: Theoretical Yield of CO₂ Reaction # 1 2 3 Experiment 1 Total mass before reaction (g) (D=A+C) 15.29 15.21g 15.25g 15.349 Exercise 1 Data Table 1 Data Table 2 Data Table 3 Data Table 4 Panel 1 Photo 1 Data Table 5 Exercise 1- Data Table 1 Data Table 2 DataTable 3 Data Table 4 Panel 1 Photo 1 Data Table 5 Exercise 1- Moles of NaHCO 0012 mol 0025 mol 0044 mol 0062 mol…

The chemical reaction you investigated is a two-step reaction. What type of reaction occurs in each step? How did you determine your answer?

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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 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