(a) Interpretation: The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted. Concept introduction: Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( RO − ). The mechanism for the epoxides under neutral or basic conditions consists of an S N 2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

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Answer 1

Question

Chapter 10, Problem 10.26P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). The mechanism for the epoxides under neutral or basic conditions consists of an SN2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn and the product of the same reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). Under acidic conditions, the first step is the protonation the C−O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite the C−O bond.

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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

Answer 2

Question

Chapter 10, Problem 10.26P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). The mechanism for the epoxides under neutral or basic conditions consists of an SN2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn and the product of the same reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). Under acidic conditions, the first step is the protonation the C−O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite the C−O bond.

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Answer 3

Question

Chapter 10, Problem 10.26P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). The mechanism for the epoxides under neutral or basic conditions consists of an SN2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn and the product of the same reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). Under acidic conditions, the first step is the protonation the C−O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite the C−O bond.

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Answer 4

Question

Chapter 10, Problem 10.26P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). The mechanism for the epoxides under neutral or basic conditions consists of an SN2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn and the product of the same reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). Under acidic conditions, the first step is the protonation the C−O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite the C−O bond.

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Answer 5

Chapter 10, Problem 10.26P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). The mechanism for the epoxides under neutral or basic conditions consists of an SN2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn and the product of the same reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). Under acidic conditions, the first step is the protonation the C−O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite the C−O bond.

Answer 6

Chapter 10, Problem 10.26P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). The mechanism for the epoxides under neutral or basic conditions consists of an SN2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

Answer 7

Chapter 10, Problem 10.26P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn and the product of the reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). The mechanism for the epoxides under neutral or basic conditions consists of an SN2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn and the product of the same reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). Under acidic conditions, the first step is the protonation the C−O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite the C−O bond.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn and the product of the same reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo nucleophilic substitution reactions in these reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (RO−). Under acidic conditions, the first step is the protonation the C−O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite the C−O bond.

Answer 10

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Answer 13

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

Solution Summary: The author explains that epoxides can undergo nucleophilic substitution reactions under neutral, basic, or acidic conditions to relieve the ring strain.

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Chapter 10 Solutions