(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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Based on the image attached, it shows methyl salicylate reacts with Ethanamine, and Ether act as a solvent to form N-ethylbenzamide as a product. Explains the mechanism reaction of conversion ester to an amide.

Synthesize octadecyl stearate using linoleic acid (18:2) (Given, stearic acid: 18:0) as the only starting material.

The reaction of ninhydrin with an -amino acid occurs in several steps (a) The first step is loss of water to give a triketone. Show the mechanism of the reaction and the structure of the triketone.(b) The second step is formation of an imine by reaction of the amino acid with the triketone. Show its structure. (c) The third step is a decarboxylation. Show the structure of the product and the mechanism of the decarboxylation reaction. (d) The fourth step is hydrolysis of an imine to yield an amine and an aldehyde. Show the structures of both products. (e) The final step is formation of the purple anion. Show the mechanism of the reaction

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Concept explainers

Videos

Want to see the full answer?

Chapter 27 Solutions