a) Interpretation: Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted. Concept introduction: Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene , the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents. To state: The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Question

1. The acid-catalyzed elimination of an alcohol is an equilibrium reaction and requires special reac- tion conditions to favour the formation of the alkene product. What chemical principle controls the amount of alkene product that is produced? Provide two laboratory techniques that can be used to obtain good alkene yields in alcohol elimination reactions.

Answer 1

Question

Chapter 7.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

b)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

c)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene assuming that Markovnikov’s rule is valid.

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1. The acid-catalyzed elimination of an alcohol is an equilibrium reaction and requires special reac- tion conditions to favour the formation of the alkene product. What chemical principle controls the amount of alkene product that is produced? Provide two laboratory techniques that can be used to obtain good alkene yields in alcohol elimination reactions.

Complete the table below with all the missing information. Note: more than one reactant/reagent/product may be required in a row/column.

What is the major organic product of this reaction sequence? Type its systematic IUPAC name in the box below. 1) HNO3, H,SO, 2) H2, Pd/C 3) NaNO,, HCI, 0 °C 4) H20, heat

Answer 2

Question

Chapter 7.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

b)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

c)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene assuming that Markovnikov’s rule is valid.

Expert Solution & Answer

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Answer 3

Question

Chapter 7.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

b)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

c)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene assuming that Markovnikov’s rule is valid.

Expert Solution & Answer

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Answer 4

Question

Chapter 7.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

b)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

c)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene assuming that Markovnikov’s rule is valid.

Expert Solution & Answer

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Answer 5

Chapter 7.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

b)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene assuming that Markovnikov’s rule is valid.

Interpretation Introduction

c)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene assuming that Markovnikov’s rule is valid.

Answer 6

Chapter 7.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Answer 7

Chapter 7.SE, Problem 59AP

Interpretation Introduction

a)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 3-methyl-3-butene assuming that Markovnikov’s rule is valid.

Answer 8

Interpretation Introduction

b)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene assuming that Markovnikov’s rule is valid.

Answer 9

Interpretation Introduction

b)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to methylidenecyclohexene assuming that Markovnikov’s rule is valid.

Answer 10

Interpretation Introduction

c)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene assuming that Markovnikov’s rule is valid.

Answer 11

Interpretation Introduction

c)

Interpretation:

Assuming Markovnikov’s rule is valid, the major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene is to be predicted.

Concept introduction:

Markovnikov’s rule can be used to decide on the orientation in electrophilic addition reactions. According to this rule, in the addition of HX to an alkene, the H attaches itself with the carbon with fewer alkyl substituents and the X attaches itself with the carbon with more alkyl substituents.

To state:

The major alcohol product obtainable by the acid-catalyzed addition of water to 4- methyl-1-pentene assuming that Markovnikov’s rule is valid.

Answer 12

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Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2P Ch. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5P Ch. 7.3 - Prob. 6P Ch. 7.3 - Prob. 7P Ch. 7.4 - Prob. 8P Ch. 7.4 - Prob. 9P Ch. 7.4 - Prob. 10P

Solution Summary: The author explains how Markovnikov's rule can be used to decide on the orientation in electrophilic addition reactions.

Chapter 7 Solutions