(a) Interpretation: The product with greater abundance in the given E1 reaction is to be predicted. Concept introduction: The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

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Answer 1

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Chapter 8, Problem 8.16P

Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

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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

fcrip = ↓ bandwidth Il temp 32. What impact (increase, decrease, or no change) does each of the following conditions have on the individual components of the van Deemter equation and consequently, band broadening? Increase temperature Longer column Using a gas mobile phase instead of liquid Smaller particle stationary phase Multiple Paths Diffusion Mass Transfer

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 8, Problem 8.16P

Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

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Answer 3

Question

Chapter 8, Problem 8.16P

Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

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Answer 4

Question

Chapter 8, Problem 8.16P

Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

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Answer 5

Chapter 8, Problem 8.16P

Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Answer 6

Chapter 8, Problem 8.16P

Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Answer 7

Chapter 8, Problem 8.16P

Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Answer 10

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Answer 13

Ch. 8 - Prob. 8.1P Ch. 8 - Prob. 8.2P Ch. 8 - Prob. 8.3P Ch. 8 - Prob. 8.4P Ch. 8 - Prob. 8.5P Ch. 8 - Prob. 8.6P Ch. 8 - Prob. 8.7P Ch. 8 - Prob. 8.8P Ch. 8 - Prob. 8.9P Ch. 8 - Prob. 8.10P

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