It is to be explained why the given reaction violates Markovnikov’s rule. Concept introduction: The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury ( II ) acetate, Hg ( OAc ) 2 , in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH 4 . The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

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Answer 1

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Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

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Answer 2

Question

Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

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Answer 3

Question

Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

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Answer 4

Question

Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

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Answer 5

Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

Answer 6

Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

Answer 7

Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

Answer 8

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Answer 10

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Answer 11

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 how the oxymercuration-reduction reaction violates Markovnikov's rule. The reaction proceeds through formation of a Mercurinium ion intermediate.

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