4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Question

Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate (c) Ethyl 2-rnethylbutanoate (d) Ethyl 2,2-dimethylpropanoate (b) Ethyl 3-methylbutanoate

Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19, Problem 19.46P

(a)

Interpretation Introduction

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(b)

Interpretation Introduction

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(c)

Interpretation Introduction

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(d)

Interpretation Introduction

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(e)

Interpretation Introduction

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(f)

Interpretation Introduction

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(g)

Interpretation Introduction

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(h)

Interpretation Introduction

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

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Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate (c) Ethyl 2-rnethylbutanoate (d) Ethyl 2,2-dimethylpropanoate (b) Ethyl 3-methylbutanoate

(b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3

Write a structural formula for each of the following compounds: (a) m-Chlorobenzoyl chloride (b) Trifluoroacetic anhydride (c) cis-1,2-Cyclopropanedicarboxylic anhydride (d) Ethyl cycloheptanecarboxylate (e) 1-Phenylethyl acetate (f) 2-Phenylethyl acetate (g) p-Ethylbenzamide (h) N-Ethylbenzamide (i) 2-Methylhexanenitrile

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19, Problem 19.46P

(a)

Interpretation Introduction

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(b)

Interpretation Introduction

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(c)

Interpretation Introduction

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(d)

Interpretation Introduction

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(e)

Interpretation Introduction

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(f)

Interpretation Introduction

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(g)

Interpretation Introduction

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(h)

Interpretation Introduction

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19, Problem 19.46P

(a)

Interpretation Introduction

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(b)

Interpretation Introduction

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(c)

Interpretation Introduction

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(d)

Interpretation Introduction

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(e)

Interpretation Introduction

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(f)

Interpretation Introduction

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(g)

Interpretation Introduction

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(h)

Interpretation Introduction

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19, Problem 19.46P

(a)

Interpretation Introduction

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(b)

Interpretation Introduction

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(c)

Interpretation Introduction

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(d)

Interpretation Introduction

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(e)

Interpretation Introduction

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(f)

Interpretation Introduction

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(g)

Interpretation Introduction

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(h)

Interpretation Introduction

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

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Answer 5

Chapter 19, Problem 19.46P

(a)

Interpretation Introduction

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(b)

Interpretation Introduction

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(c)

Interpretation Introduction

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(d)

Interpretation Introduction

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(e)

Interpretation Introduction

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(f)

Interpretation Introduction

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(g)

Interpretation Introduction

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

(h)

Interpretation Introduction

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 6

Chapter 19, Problem 19.46P

(a)

Interpretation Introduction

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 7

Chapter 19, Problem 19.46P

(a)

Interpretation Introduction

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 8

(b)

Interpretation Introduction

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 9

(b)

Interpretation Introduction

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 10

(c)

Interpretation Introduction

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 11

(c)

Interpretation Introduction

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 12

(d)

Interpretation Introduction

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 13

(d)

Interpretation Introduction

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 14

(e)

Interpretation Introduction

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 15

(e)

Interpretation Introduction

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 16

(f)

Interpretation Introduction

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 17

(f)

Interpretation Introduction

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 18

(g)

Interpretation Introduction

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 19

(g)

Interpretation Introduction

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 20

(h)

Interpretation Introduction

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 21

(h)

Interpretation Introduction

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Answer 22

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Answer 23

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Answer 27

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Answer 33

Ch. 19.2 - Prob. 19.1P Ch. 19.2 - Prob. 19.2P Ch. 19.2 - Prob. 19.3P Ch. 19.3 - Prob. 19.4P Ch. 19.3 - Prob. 19.5P Ch. 19.3 - Prob. 19.6P Ch. 19.5 - Prob. 19.7P Ch. 19.5 - Prob. 19.8P Ch. 19.5 - Prob. 19.9P Ch. 19.6 - Prob. 19.10P

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: 4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: 2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: 3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: 2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: 4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: 3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation: Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Chapter 19 Solutions

Interpretation:

4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation:

2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation:

3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation:

2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation:

4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation:

3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation:

Cyclopropane carboxylic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.

Interpretation:

Cyclobutylmethyl ketone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.