Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated. Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α − substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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Answer 1

Question

Chapter 18.18, Problem 38P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(d)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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Draw the line angle diagram of two other functional groups that act as electrophiles in the presence of a nucleophile (or basic conditions). Write the names of the functional groups under each structure.

What alkyl bromide(s) should be used in the malonic ester synthesis of each of the following carboxylic acids? a. propanoic acid c. 3-phenylpropanoic acid b. 2-methylpropanoic acid d. 4-methylpentanoic acid

what would the final product be using the reagents given.

Answer 2

Question

Chapter 18.18, Problem 38P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(d)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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Answer 3

Question

Chapter 18.18, Problem 38P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(d)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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Answer 4

Question

Chapter 18.18, Problem 38P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(d)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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Answer 5

Chapter 18.18, Problem 38P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

(d)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 6

Chapter 18.18, Problem 38P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 7

Chapter 18.18, Problem 38P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid has to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 8

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 9

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 10

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 11

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 12

(d)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 13

(d)

Interpretation Introduction

Interpretation: Alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a α hydrogen atom. The anion so formed is reacted with an alkyl bromide. Th anion abstracts the alkyl group from the alkyl bromide. Acidic hydrolysis of the intermediate so formed gives α−substituted malonic acid. On heating, decarboxylation takes place which gives the desired carboxylic acid.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 18.1 - Prob. 1P Ch. 18.1 - Prob. 2P Ch. 18.1 - Prob. 3P Ch. 18.1 - Prob. 4P Ch. 18.1 - PROBLEM 5♦ List the compounds in each of the...Ch. 18.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 18.3 - Draw the enol tautomers for each of the following...Ch. 18.3 - Prob. 8P Ch. 18.4 - Prob. 9P Ch. 18.4 - Prob. 10P

Solution Summary: The author explains that alkyl bromide used in the malonic ester synthesis of each carboxylic acid is to be stated.

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