(a) Interpretation: The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn. Concept introduction: A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C − site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P ( C 6 H 5 ) 3 , followed by a very strong base such as butyllithium.

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Answer 1

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Chapter 17, Problem 17.73P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Interpretation Introduction

(b)

Interpretation:

It is to be explained why the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene does not undergo nucleophilic addition with ketones or aldehydes.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Cyclic planar compounds with cyclic conjugation, which obeys Huckel’s rule of (4n+2π) electrons, are said to aromatic. The addition reaction destroys the aromaticity, which, in turn, lowers the stability; thus aromatic compounds do not undergo addition reactions to retain the aromaticity.

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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 17, Problem 17.73P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Interpretation Introduction

(b)

Interpretation:

It is to be explained why the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene does not undergo nucleophilic addition with ketones or aldehydes.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Cyclic planar compounds with cyclic conjugation, which obeys Huckel’s rule of (4n+2π) electrons, are said to aromatic. The addition reaction destroys the aromaticity, which, in turn, lowers the stability; thus aromatic compounds do not undergo addition reactions to retain the aromaticity.

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Answer 3

Question

Chapter 17, Problem 17.73P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Interpretation Introduction

(b)

Interpretation:

It is to be explained why the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene does not undergo nucleophilic addition with ketones or aldehydes.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Cyclic planar compounds with cyclic conjugation, which obeys Huckel’s rule of (4n+2π) electrons, are said to aromatic. The addition reaction destroys the aromaticity, which, in turn, lowers the stability; thus aromatic compounds do not undergo addition reactions to retain the aromaticity.

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Answer 4

Question

Chapter 17, Problem 17.73P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Interpretation Introduction

(b)

Interpretation:

It is to be explained why the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene does not undergo nucleophilic addition with ketones or aldehydes.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Cyclic planar compounds with cyclic conjugation, which obeys Huckel’s rule of (4n+2π) electrons, are said to aromatic. The addition reaction destroys the aromaticity, which, in turn, lowers the stability; thus aromatic compounds do not undergo addition reactions to retain the aromaticity.

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Answer 5

Chapter 17, Problem 17.73P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Interpretation Introduction

(b)

Interpretation:

It is to be explained why the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene does not undergo nucleophilic addition with ketones or aldehydes.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Cyclic planar compounds with cyclic conjugation, which obeys Huckel’s rule of (4n+2π) electrons, are said to aromatic. The addition reaction destroys the aromaticity, which, in turn, lowers the stability; thus aromatic compounds do not undergo addition reactions to retain the aromaticity.

Answer 6

Chapter 17, Problem 17.73P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Answer 7

Chapter 17, Problem 17.73P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism showing the formation of the Wittig reagent from 5-bromo-1, 3-cyclopentadiene using the reagents provided in the given reaction equation is to be drawn.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Answer 8

Interpretation Introduction

(b)

Interpretation:

It is to be explained why the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene does not undergo nucleophilic addition with ketones or aldehydes.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Cyclic planar compounds with cyclic conjugation, which obeys Huckel’s rule of (4n+2π) electrons, are said to aromatic. The addition reaction destroys the aromaticity, which, in turn, lowers the stability; thus aromatic compounds do not undergo addition reactions to retain the aromaticity.

Answer 9

Interpretation Introduction

(b)

Interpretation:

It is to be explained why the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene does not undergo nucleophilic addition with ketones or aldehydes.

Concept introduction:

A Wittig reagent, also called a phosphonium ylide, is highly nucleophilic at the C− site. To generate a Wittig reagent, the alkyl halide is treated with triphenylphosphine, P(C6H5)3, followed by a very strong base such as butyllithium.

Cyclic planar compounds with cyclic conjugation, which obeys Huckel’s rule of (4n+2π) electrons, are said to aromatic. The addition reaction destroys the aromaticity, which, in turn, lowers the stability; thus aromatic compounds do not undergo addition reactions to retain the aromaticity.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 17 - Prob. 17.1P Ch. 17 - Prob. 17.2P Ch. 17 - Prob. 17.3P Ch. 17 - Prob. 17.4P Ch. 17 - Prob. 17.5P Ch. 17 - Prob. 17.6P Ch. 17 - Prob. 17.7P Ch. 17 - Prob. 17.8P Ch. 17 - Prob. 17.9P Ch. 17 - Prob. 17.10P

Solution Summary: The author explains the mechanism of the Wittig reagent generated from 5-bromo-1, 3-cyclopentadiene.

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Chapter 17 Solutions