(a) Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized. Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone .

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Answer 1

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Chapter 23, Problem 23.29P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via SN2 mechanism.

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Nabumetone is a pain reliever and anti-inammatory agent sold under the brand name of Relafen.a. Write out a synthesis of nabumetone from ethyl acetoacetate.b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?

a. What two amides are obtained from the reaction of acetyl chloride with an equivalent of ethylamine and an equivalent of propylamine?b. Why is only one amide obtained from the reaction of acetyl chloride with an equivalent of ethylamine and an equivalent of triethylamine?

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system. a. How can tyramine be prepared from β-phenylethylamine?b. How can dopamine be prepared from tyramine?c. Give two ways to prepare β-phenylethylamine from β-phenylethyl chloride.d. How can β-phenylethylamine be prepared from benzyl chloride?e. How can β-phenylethylamine be prepared from benzaldehyde?

Answer 2

Question

Chapter 23, Problem 23.29P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via SN2 mechanism.

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Answer 3

Question

Chapter 23, Problem 23.29P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via SN2 mechanism.

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Answer 4

Question

Chapter 23, Problem 23.29P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via SN2 mechanism.

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Answer 5

Chapter 23, Problem 23.29P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via SN2 mechanism.

Answer 6

Chapter 23, Problem 23.29P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Answer 7

Chapter 23, Problem 23.29P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Answer 8

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via SN2 mechanism.

Answer 9

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via SN2 mechanism.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

(a) Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized. Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone .

Solution Summary: The author explains the synthesis of nabumetone from ethyl acetoacetate.

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Chapter 23 Solutions

Solution Summary: The author explains the synthesis of nabumetone from ethyl acetoacetate.

Concept explainers

(a) Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized. Concept introduction: The α hydrogen attached to the β- ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

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Chapter 23 Solutions