(a) Interpretation: For the given pair of substrates, it is to be explained which one will undergo an S N 1 reaction faster. Concept introduction: In S N 1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate. The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

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Answer 1

Question

Chapter 14, Problem 14.63P

Interpretation Introduction

(a)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Interpretation Introduction

(b)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

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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 14, Problem 14.63P

Interpretation Introduction

(a)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Interpretation Introduction

(b)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

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Answer 3

Question

Chapter 14, Problem 14.63P

Interpretation Introduction

(a)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Interpretation Introduction

(b)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

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Answer 4

Question

Chapter 14, Problem 14.63P

Interpretation Introduction

(a)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Interpretation Introduction

(b)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

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Answer 5

Chapter 14, Problem 14.63P

Interpretation Introduction

(a)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Interpretation Introduction

(b)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Answer 6

Chapter 14, Problem 14.63P

Interpretation Introduction

(a)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Answer 7

Chapter 14, Problem 14.63P

Interpretation Introduction

(a)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Answer 8

Interpretation Introduction

(b)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Answer 9

Interpretation Introduction

(b)

Interpretation:

For the given pair of substrates, it is to be explained which one will undergo an SN1 reaction faster.

Concept introduction:

In SN1 reaction, the first, rate-determining step involves removal of the leaving group to form a carbocation. The stability of the carbocation decides the speed it is formed. Since this is the rate-determining step, the overall reaction rate depends on the stability of the carbocation. The more stable the carbocation, the faster the reaction rate.

The stability of a carbocation depends mainly on two factors, the number of substituents on the same carbon and the number of atoms over which the charge may be delocalized. The higher the number of substituents on the carbocation, the more its stability. The more the number of atoms over which the charge is delocalized, the higher the stability o the carbocation.

Answer 10

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Answer 11

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Answer 13

Ch. 14 - Prob. 14.1P Ch. 14 - Prob. 14.2P Ch. 14 - Prob. 14.3P Ch. 14 - Prob. 14.4P Ch. 14 - Prob. 14.5P Ch. 14 - Prob. 14.6P Ch. 14 - Prob. 14.7P Ch. 14 - Prob. 14.8P Ch. 14 - Prob. 14.9P Ch. 14 - Prob. 14.10P

Solution Summary: The author explains which substrate will undergo an S_N1 reaction faster based on the stability of the carbocation.

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