(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

Identify the structure of the PTH derivative generated after two rounds of Edman degradation.

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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Identify the structure of the PTH derivative generated after two rounds of Edman degradation.

Use the data below from an electron impact mass spectrum of a pure compound to deduce its structure. Draw your structure in the drawing window. Data selected from the NIST WebBook, https://webbook.nist.gov/chemistry/ m/z Relative intensity 31 0.5 30 26 29 22 28 100 27 33 26 23 15 4 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. 妊 n ? Previous Next

for this question. Write the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M+ = 98.1106. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 1.008 12C 98.90 12.000 14N 99.63 14.003 160 99.76 15.995 Molecular formula (In the order CHNO, with no subscripts)

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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