(a) Interpretation: The mechanism with the organic product(s) for the given reaction is to be drawn. Concept introduction: Oxymercuration–reduction is a method to add H 2 O across carbon-carbon double bond or carbon-carbon triple bond. Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile ( H 2 O ) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone .

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Answer 1

Question

Chapter 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

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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 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

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Answer 3

Question

Chapter 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

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Answer 4

Question

Chapter 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

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Answer 5

Chapter 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Answer 6

Chapter 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Answer 7

Chapter 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add H2O across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (H2O) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 12 - Prob. 12.1P Ch. 12 - Prob. 12.2P Ch. 12 - Prob. 12.3P Ch. 12 - Prob. 12.4P Ch. 12 - Prob. 12.5P Ch. 12 - Prob. 12.6P Ch. 12 - Prob. 12.7P Ch. 12 - Prob. 12.8P Ch. 12 - Prob. 12.9P Ch. 12 - Prob. 12.10P

Solution Summary: The author explains that Oxymercuration-reduction is a method to add mercurinium ion intermediates and water to an alkene or alkyne.

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