To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined. Concept Introduction: Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an − OH protecting group is needed to stop the hindrance and facilitate the reaction to occur. After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

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Answer 1

Question

Chapter 12.7, Problem 18CC

(a)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

(b)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule has to undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting group is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

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Draw the major organic substitution product or products for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. Clearly drawn the stereochemistry, including a wedged bond, a dashed bond and two in-plane bonds at each stereogenic center. Omit any byproducts. Bri CH3CH2O- (conc.) Draw the major organic product or products.

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Answer 2

Question

Chapter 12.7, Problem 18CC

(a)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

(b)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule has to undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting group is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

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Answer 3

Question

Chapter 12.7, Problem 18CC

(a)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

(b)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule has to undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting group is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

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Answer 4

Question

Chapter 12.7, Problem 18CC

(a)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

(b)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule has to undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting group is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

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Answer 5

Chapter 12.7, Problem 18CC

(a)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

(b)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule has to undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting group is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

Answer 6

Chapter 12.7, Problem 18CC

(a)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

Answer 7

Chapter 12.7, Problem 18CC

(a)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule must undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting reagent is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule has to undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting group is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To obtain the desired product, the reactant molecule has to undergo a Grignard reaction and needs a protecting group to facilitate the reaction to occur. The protecting group is to be determined.

Concept Introduction:

Normally, an aryl bromide can directly be converted to arylmagnesium halide by reaction with Magnesium. But in this case, there is the presence of an acidic alcoholic group which can hinder the formation of Grignard reagent, which is a strong base. To prevent this, an −OH protecting group is needed to stop the hindrance and facilitate the reaction to occur.

After the formation of the Grignard reagent, it can be coupled with a suitable reactant, followed by deprotection, to obtain the final product.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 12.1 - Prob. 1LTS Ch. 12.1 - Prob. 1PTS Ch. 12.1 - Prob. 2ATS Ch. 12.1 - Prob. 3CC Ch. 12.2 - Prob. 4CC Ch. 12.3 - Prob. 8CC Ch. 12.3 - Prob. 9CC Ch. 12.4 - Prob. 3LTS Ch. 12.4 - Prob. 10PTS Ch. 12.4 - Prob. 11ATS

Solution Summary: The author explains that the reactant molecule must undergo a Grignard reaction to obtain the desired product.

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Chapter 12 Solutions