(a) Interpretation: How to prepare the given compound from an alkene is to be explained. Concept introduction: The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH 3 < 1 o < 2 o < 3 o . The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation. The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury ( II ) acetate, Hg ( OAc ) 2 , in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH 4 . The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

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Answer 1

Question

Chapter 12, Problem 12.43P

Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

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Answer 2

Question

Chapter 12, Problem 12.43P

Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

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Answer 3

Question

Chapter 12, Problem 12.43P

Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

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Answer 4

Question

Chapter 12, Problem 12.43P

Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

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Answer 5

Chapter 12, Problem 12.43P

Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Answer 6

Chapter 12, Problem 12.43P

Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Answer 7

Chapter 12, Problem 12.43P

Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3 < 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

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 how to prepare the given compound from an alkene by electrophilic addition of water across the C=C bond in an acidic condition.

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Chapter 12 Solutions