(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

Please predict the product of the following reaction, and draw the complete, detailed mechanism.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Please predict the product of the following reaction, and draw the complete, detailed mechanism.

Draw the complete, detailed mechanism for each of the following reactions and predict the major products.

Determine the major product of each reaction in Problem and draw the complete, detailed mechanism. Pay attention to stereochemistry where appropriate.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 15

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 16

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 17

Trending nowThis is a popular solution!

Answer 18

Trending nowThis is a popular solution!

Answer 19

Trending nowThis is a popular solution!

Answer 20

Trending now

Answer 21

This is a popular solution!

Answer 22

See solution

Check out sample textbook solution

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.

Concept explainers

Videos

Chapter 12 Solutions