(a) Interpretation: The steps to carry out the given transformation is to be shown. Concept introduction: An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C − B bond is replaced by the C − OH bond.

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Answer 1

Question

Chapter 12, Problem 12.24P

Interpretation Introduction

(a)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C−B bond is replaced by the C−OH bond.

Interpretation Introduction

(b)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry. The 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 with the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(c)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. The 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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Draw the reaction mechanism to predict the product of the transformation below: N H ? H₂O

Answer 2

Question

Chapter 12, Problem 12.24P

Interpretation Introduction

(a)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C−B bond is replaced by the C−OH bond.

Interpretation Introduction

(b)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry. The 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 with the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(c)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. The 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 12.24P

Interpretation Introduction

(a)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C−B bond is replaced by the C−OH bond.

Interpretation Introduction

(b)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry. The 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 with the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(c)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. The 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 12.24P

Interpretation Introduction

(a)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C−B bond is replaced by the C−OH bond.

Interpretation Introduction

(b)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry. The 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 with the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(c)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. The 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 12.24P

Interpretation Introduction

(a)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C−B bond is replaced by the C−OH bond.

Interpretation Introduction

(b)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry. The 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 with the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Interpretation Introduction

(c)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. The 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 12.24P

Interpretation Introduction

(a)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C−B bond is replaced by the C−OH bond.

Answer 7

Chapter 12, Problem 12.24P

Interpretation Introduction

(a)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry while hydroboration-oxidation follows anti Markovnikov’s regiochemistry. In hydroboration-oxidation, the partially negative hydrogen atom forms a bond with most substituted carbon while the boron ends up attached to the least substituted carbon atom. In the final product, the C−B bond is replaced by the C−OH bond.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry. The 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 with the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reaction follows Markovnikov’s regiochemistry. The 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 with the carbon atom that can better stabilize a positive charge. Rearrangement generally does not take place with oxymercuration–reduction.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. The 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:

The steps to carry out the given transformation is to be shown.

Concept introduction:

An alkene can be converted to an alcohol in many ways, out of which, the oxymercuration-reduction, and an acid-catalyzed hydration reactions follow Markovnikov’s regiochemistry. The 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 15

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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