(a) Interpretation: How to bring out the given transformation is to be presented. Concept introduction: An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the − OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Question

Problem 54, could you please explain it in detail? Thank you! Step by step, I'm really confused, so please don't make it overly complex. My question is to visually draw it out and demonstrate it to me; I'm confused about that problem, please (not just in words) but demonstrate it to me in all due essence (visually) with descriptions.

Answer 1

Question

Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

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Answer 2

Question

Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

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Answer 3

Question

Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

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Answer 4

Question

Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

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Answer 5

Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Answer 6

Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Answer 7

Chapter 12, Problem 12.23P

Interpretation Introduction

(a)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. The hydrogen atom finishes up bound to the highly substituted carbon, and boron finishes up attached to the fewer substituted carbon atom in the double bond.

Answer 10

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Answer 11

Interpretation Introduction

(c)

Interpretation:

How to bring out the given transformation is to be presented.

Concept introduction:

An alkene can be converted to an alcohol by many ways, out of which, oxymercuration-reduction and acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. Oxymercuration-reduction does not go through the carbocation intermediate, so no carbocation rearrangements occur with this mechanism. On the other hand, carbocation rearrangements are possible in acid-catalyzed addition of water. The product of oxymercuration-reduction is the one expected from Markovnikov’s rule, that is, the −OH group forms a bond to the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Answer 12

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Answer 23

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 an alkene can be converted to an alcohol by oxymercuration-reduction and acid-catalyzed hydration reactions.

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