(a) Interpretation: The given amino acid is to be prepared using acetoamidomalonate method. Concept Introduction: The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide . Then, hydrolysis of intermediate compound takes place which results in product formation. Answer: The synthesis of given amino acid using acetoamidomalonate method is shown below. Explanation: The given isobutylene reacts with DBr/H 2 O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below. Figure 1 Conclusion: The complete synthesis of given compound is shown in Figure 1.

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Answer 1

Question

Chapter 27, Problem 27.72AP

Interpretation Introduction

(a)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer:

The synthesis of given amino acid using acetoamidomalonate method is shown below.

Explanation:

The given isobutylene reacts with DBr/H₂O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below.

Figure 1

Conclusion:

The complete synthesis of given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Interpretation Introduction

(c)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

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Please answer the question and provide a detailed drawing of the structure. If there will not be a new C – C bond, then the box under the drawing area will be checked. Will the following reaction make a molecule with a new C – C bond as its major product: Draw the major organic product or products, if the reaction will work. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry.

Please do not use AI. AI cannot "see" the molecules properly, and it therefore gives the wrong answer while giving incorrect descriptions of the visual images we're looking at. All of these compounds would be produced (I think). In my book, I don't see any rules about yield in this case, like explaining that one product would be present in less yield for this reason or that reason. Please explain why some of these produce less yield than others.

Please answer the question and provide detailed explanations.

Answer 2

Question

Chapter 27, Problem 27.72AP

Interpretation Introduction

(a)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer:

The synthesis of given amino acid using acetoamidomalonate method is shown below.

Explanation:

The given isobutylene reacts with DBr/H₂O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below.

Figure 1

Conclusion:

The complete synthesis of given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Interpretation Introduction

(c)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

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Answer 3

Question

Chapter 27, Problem 27.72AP

Interpretation Introduction

(a)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer:

The synthesis of given amino acid using acetoamidomalonate method is shown below.

Explanation:

The given isobutylene reacts with DBr/H₂O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below.

Figure 1

Conclusion:

The complete synthesis of given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Interpretation Introduction

(c)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

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Answer 4

Question

Chapter 27, Problem 27.72AP

Interpretation Introduction

(a)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer:

The synthesis of given amino acid using acetoamidomalonate method is shown below.

Explanation:

The given isobutylene reacts with DBr/H₂O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below.

Figure 1

Conclusion:

The complete synthesis of given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Interpretation Introduction

(c)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

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Answer 5

Chapter 27, Problem 27.72AP

Interpretation Introduction

(a)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer:

The synthesis of given amino acid using acetoamidomalonate method is shown below.

Explanation:

The given isobutylene reacts with DBr/H₂O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below.

Figure 1

Conclusion:

The complete synthesis of given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Interpretation Introduction

(c)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer 6

Chapter 27, Problem 27.72AP

Interpretation Introduction

(a)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer:

The synthesis of given amino acid using acetoamidomalonate method is shown below.

Explanation:

The given isobutylene reacts with DBr/H₂O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below.

Figure 1

Conclusion:

The complete synthesis of given compound is shown in Figure 1.

Answer 7

Chapter 27, Problem 27.72AP

Interpretation Introduction

(a)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion form reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer:

The synthesis of given amino acid using acetoamidomalonate method is shown below.

Explanation:

The given isobutylene reacts with DBr/H₂O to form bromoisobutane. Diethylacetamidomalonate forms enolate ion in the presence of sodium ethoxide and ethanol. Then enolate ion is alkylated with bromoisobutane. The compound formed is treated with hot aqueous hydrogen bromide. First, the ester hydrolysis takes place. Second, the decarboxylation of carboxylic group takes place. Third, acetamido group and amide gets hydrolysed. This results in the product formation. The complete reaction is shown below.

Figure 1

Conclusion:

The complete synthesis of given compound is shown in Figure 1.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The given amino acid is to be prepared using acetoamidomalonate method.

Concept Introduction:

The method used for preparation of α- amino acid is acetoamidomalonate method. In this reaction, diethylacetamidomalonate reacts with sodium ethoxide and ethanol to form enolate ion. The enolate ion forms reacts with alkyl halide. Then, hydrolysis of intermediate compound takes place which results in product formation.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 27 - Prob. 27.1P Ch. 27 - Prob. 27.2P Ch. 27 - Prob. 27.3P Ch. 27 - Prob. 27.4P Ch. 27 - Prob. 27.5P Ch. 27 - Prob. 27.6P Ch. 27 - Prob. 27.8P Ch. 27 - Prob. 27.9P Ch. 27 - Prob. 27.10P Ch. 27 - Prob. 27.11P

Solution Summary: The author explains how the amino acid is prepared using acetoamidomalonate method.

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