A structure for the compound A, C 4 H 8 O 3 , with the following spectral characteristics is to be proposed. I R: 1710 cm -1 , 2500 cm -1 , 3100 cm -1 . 1.26 δ (Rel.area:3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00). Concept introduction: In IR, the carboxyl carbonyl in cyclopentanecarboxylic acid absorbs at 1725 cm -1 while the OH absorption is seen as a characteristic broad band in the range 2500-3300 cm -1 . In 1 HNMR, the acidic COOH proton normally absorbs as singlet, broadened in few cases, near 12 δ. To propose: A structure for the compound A, C 4 H 8 O 3 , with the following spectral characteristics is to be proposed. I R: 1710 cm -1 , 2500 cm -1 , 3100 cm -1 . 1 HNMR: 1.26 δ (Rel.area: 3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

Question

Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.

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 20.SE, Problem 56AP

Interpretation Introduction

Interpretation:

A structure for the compound A, C₄H₈O₃, with the following spectral characteristics is to be proposed.

I R: 1710 cm^-1, 2500 cm^-1, 3100 cm^-1.

1.26 δ (Rel.area:3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

Concept introduction:

In IR, the carboxyl carbonyl in cyclopentanecarboxylic acid absorbs at 1725 cm^-1 while the OH absorption is seen as a characteristic broad band in the range 2500-3300 cm^-1.

In ¹HNMR, the acidic COOH proton normally absorbs as singlet, broadened in few cases, near 12 δ.

To propose:

A structure for the compound A, C₄H₈O₃, with the following spectral characteristics is to be proposed.

I R: 1710 cm^-1, 2500 cm^-1, 3100 cm^-1.

¹HNMR: 1.26 δ (Rel.area: 3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

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Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.

Compound P has molecular formula C5H9C102. Deduce the structure of P from its 1H and 13C NMR spectra.

Propose a structure for D (molecular formula C9H9ClO2) consistent with the given spectroscopic data. 13C NMR signals at 30, 36, 128, 130, 133, 139, and 179 ppm

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 20.SE, Problem 56AP

Interpretation Introduction

Interpretation:

A structure for the compound A, C₄H₈O₃, with the following spectral characteristics is to be proposed.

I R: 1710 cm^-1, 2500 cm^-1, 3100 cm^-1.

1.26 δ (Rel.area:3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

Concept introduction:

In IR, the carboxyl carbonyl in cyclopentanecarboxylic acid absorbs at 1725 cm^-1 while the OH absorption is seen as a characteristic broad band in the range 2500-3300 cm^-1.

In ¹HNMR, the acidic COOH proton normally absorbs as singlet, broadened in few cases, near 12 δ.

To propose:

A structure for the compound A, C₄H₈O₃, with the following spectral characteristics is to be proposed.

I R: 1710 cm^-1, 2500 cm^-1, 3100 cm^-1.

¹HNMR: 1.26 δ (Rel.area: 3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

Expert Solution & Answer

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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 20.SE, Problem 56AP

Interpretation Introduction

Interpretation:

A structure for the compound A, C₄H₈O₃, with the following spectral characteristics is to be proposed.

I R: 1710 cm^-1, 2500 cm^-1, 3100 cm^-1.

1.26 δ (Rel.area:3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

Concept introduction:

In IR, the carboxyl carbonyl in cyclopentanecarboxylic acid absorbs at 1725 cm^-1 while the OH absorption is seen as a characteristic broad band in the range 2500-3300 cm^-1.

In ¹HNMR, the acidic COOH proton normally absorbs as singlet, broadened in few cases, near 12 δ.

To propose:

A structure for the compound A, C₄H₈O₃, with the following spectral characteristics is to be proposed.

I R: 1710 cm^-1, 2500 cm^-1, 3100 cm^-1.

¹HNMR: 1.26 δ (Rel.area: 3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

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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 20.SE, Problem 56AP

Interpretation Introduction