(a) Interpretation: The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn. Concept introduction: In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp 3 hybridized carbon atoms in the product ring.

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Answer 1

Question

Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp3 hybridized carbon atoms in the product ring.

Interpretation Introduction

(b)

Interpretation:

It is to be explained whether the Birch reduction of toluene occurs faster or slower than the Birch reduction of benzene itself.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. Since the nucleophile in this reaction is essentially free electrons, the reaction is faster on aromatic rings with electron-withdrawing substituents and slower on aromatic rings with electron-donating substituents.

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(a 4 shows scanning electron microscope (SEM) images of extruded actions of packing bed for two capillary columns of different diameters, al 750 (bottom image) and b) 30-μm-i.d. Both columns are packed with the same stationary phase, spherical particles with 1-um diameter. A) When the columns were prepared, the figure shows that the column with the larger diameter has more packing irregularities. Explain this observation. B) Predict what affect this should have on band broadening and discuss your prediction using the van Deemter terms. C) Does this figure support your explanations in application question 33? Explain why or why not and make any changes in your answers in light of this figure. Figure 4 SEM images of sections of packed columns for a) 750 and b) 30-um-i.d. capillary columns.³

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34. Figure 3 shows Van Deemter plots for a solute molecule using different column inner diameters (i.d.). A) Predict whether decreasing the column inner diameters increase or decrease bandwidth. B) Predict which van Deemter equation coefficient (A, B, or C) has the greatest effect on increasing or decreasing bandwidth as a function of i.d. and justify your answer. Figure 3 Van Deemter plots for hydroquinone using different column inner diameters (i.d. in μm). The data was obtained from liquid chromatography experiments using fused-silica capillary columns packed with 1.0-μm particles. 35 20 H(um) 큰 20 15 90 0+ 1500 100 75 550 01 02 594 05 μ(cm/sec) 30 15 10

Answer 2

Question

Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp3 hybridized carbon atoms in the product ring.

Interpretation Introduction

(b)

Interpretation:

It is to be explained whether the Birch reduction of toluene occurs faster or slower than the Birch reduction of benzene itself.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. Since the nucleophile in this reaction is essentially free electrons, the reaction is faster on aromatic rings with electron-withdrawing substituents and slower on aromatic rings with electron-donating substituents.

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Answer 3

Question

Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp3 hybridized carbon atoms in the product ring.

Interpretation Introduction

(b)

Interpretation:

It is to be explained whether the Birch reduction of toluene occurs faster or slower than the Birch reduction of benzene itself.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. Since the nucleophile in this reaction is essentially free electrons, the reaction is faster on aromatic rings with electron-withdrawing substituents and slower on aromatic rings with electron-donating substituents.

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Answer 4

Question

Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp3 hybridized carbon atoms in the product ring.

Interpretation Introduction

(b)

Interpretation:

It is to be explained whether the Birch reduction of toluene occurs faster or slower than the Birch reduction of benzene itself.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. Since the nucleophile in this reaction is essentially free electrons, the reaction is faster on aromatic rings with electron-withdrawing substituents and slower on aromatic rings with electron-donating substituents.

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Answer 5

Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp3 hybridized carbon atoms in the product ring.

Interpretation Introduction

(b)

Interpretation:

It is to be explained whether the Birch reduction of toluene occurs faster or slower than the Birch reduction of benzene itself.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. Since the nucleophile in this reaction is essentially free electrons, the reaction is faster on aromatic rings with electron-withdrawing substituents and slower on aromatic rings with electron-donating substituents.

Answer 6

Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp3 hybridized carbon atoms in the product ring.

Answer 7

Chapter 25, Problem 25.61P

Interpretation Introduction

(a)

Interpretation:

The mechanism that leads to the formation of the major product when toluene undergoes Birch reduction is to be drawn.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. The initial step of the Birch reduction is a one-electron transfer into the aromatic system. The product is a radical anion. This product is protonated by the solvent, which gives cyclohexadienyl radical. By an additional one-electron transfer, the allyl radical is resonance stabilized and transformed into a cyclohexadienyl anion. Afterward, the cyclohexadienyl anion is also protonated by the solvent molecules. This produces the final product. Electron-donating substituents such as alkoxy or alkyl groups are located at one of the double bonds of the final product. The carboxyl or amide is electron-withdrawing group. These groups are situated at one of the sp3 hybridized carbon atoms in the product ring.

Answer 8

Interpretation Introduction

(b)

Interpretation:

It is to be explained whether the Birch reduction of toluene occurs faster or slower than the Birch reduction of benzene itself.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. Since the nucleophile in this reaction is essentially free electrons, the reaction is faster on aromatic rings with electron-withdrawing substituents and slower on aromatic rings with electron-donating substituents.

Answer 9

Interpretation Introduction

(b)

Interpretation:

It is to be explained whether the Birch reduction of toluene occurs faster or slower than the Birch reduction of benzene itself.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. The dissolving metal reduction of a benzene ring is called Birch reduction, which yields a cyclohexa-1, 4-diene as the major product. Birch reduction is accomplished in liquid ammonia with dissolved sodium metal. The anionic intermediates is protonated by ethanol as a solvent. Since the nucleophile in this reaction is essentially free electrons, the reaction is faster on aromatic rings with electron-withdrawing substituents and slower on aromatic rings with electron-donating substituents.

Answer 10

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Answer 13

Ch. 25 - Prob. 25.1P Ch. 25 - Prob. 25.2P Ch. 25 - Prob. 25.3P Ch. 25 - Prob. 25.4P Ch. 25 - Prob. 25.5P Ch. 25 - Prob. 25.6P Ch. 25 - Prob. 25.7P Ch. 25 - Prob. 25.8P Ch. 25 - Prob. 25.9P Ch. 25 - Prob. 25.10P

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