ORGANIC CHEM +SG +SAPLING >IP<
ORGANIC CHEM +SG +SAPLING >IP<
6th Edition
ISBN: 9781319171179
Author: LOUDON
Publisher: MAC HIGHER
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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.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 27, Problem 27.72AP , additional homework tip  1

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.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 27, Problem 27.72AP , additional homework tip  2Figure 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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Chapter 27 Solutions

ORGANIC CHEM +SG +SAPLING >IP<

Ch. 27 - Prob. 27.12PCh. 27 - Prob. 27.13PCh. 27 - Prob. 27.14PCh. 27 - Prob. 27.15PCh. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Prob. 27.18PCh. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Prob. 27.25PCh. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - Prob. 27.43APCh. 27 - Prob. 27.44APCh. 27 - Prob. 27.45APCh. 27 - Prob. 27.46APCh. 27 - Prob. 27.47APCh. 27 - Prob. 27.48APCh. 27 - Prob. 27.49APCh. 27 - Prob. 27.50APCh. 27 - Prob. 27.51APCh. 27 - Prob. 27.52APCh. 27 - Prob. 27.53APCh. 27 - Prob. 27.54APCh. 27 - Prob. 27.55APCh. 27 - Prob. 27.56APCh. 27 - Prob. 27.57APCh. 27 - Prob. 27.58APCh. 27 - Prob. 27.59APCh. 27 - Prob. 27.60APCh. 27 - Prob. 27.61APCh. 27 - Prob. 27.62APCh. 27 - Prob. 27.63APCh. 27 - Prob. 27.64APCh. 27 - Prob. 27.65APCh. 27 - Prob. 27.66APCh. 27 - Prob. 27.67APCh. 27 - Prob. 27.68APCh. 27 - Prob. 27.69APCh. 27 - Prob. 27.70APCh. 27 - Prob. 27.71APCh. 27 - Prob. 27.72APCh. 27 - Prob. 27.73APCh. 27 - Prob. 27.74APCh. 27 - Prob. 27.75APCh. 27 - Prob. 27.76APCh. 27 - Prob. 27.77APCh. 27 - Prob. 27.78APCh. 27 - Prob. 27.79APCh. 27 - Prob. 27.80APCh. 27 - Prob. 27.81APCh. 27 - Prob. 27.82APCh. 27 - Prob. 27.83AP
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