(a) Interpretation: The structure of optically inactive compound A with the molecular formula C 6 H 10 O 4 that follows the given NMR data and can be resolved into enantiomers is to be stated. Concept introduction: Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

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Answer 1

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Chapter 20, Problem 20.57AP

Interpretation Introduction

(a)

Interpretation:

The structure of optically inactive compound A with the molecular formula C6H10O4 that follows the given NMR data and can be resolved into enantiomers is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Interpretation Introduction

(b)

Interpretation:

The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

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The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.

An unknown compound C3H2NCl shows moderately strong IR absorptions around 1650 cm-1 and 2200 cm-1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ 5.9 and δ 7.1. Propose a structure consistent with this data?

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Answer 2

Question

Chapter 20, Problem 20.57AP

Interpretation Introduction

(a)

Interpretation:

The structure of optically inactive compound A with the molecular formula C6H10O4 that follows the given NMR data and can be resolved into enantiomers is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Interpretation Introduction

(b)

Interpretation:

The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

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Answer 3

Question

Chapter 20, Problem 20.57AP

Interpretation Introduction

(a)

Interpretation:

The structure of optically inactive compound A with the molecular formula C6H10O4 that follows the given NMR data and can be resolved into enantiomers is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Interpretation Introduction

(b)

Interpretation:

The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

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Answer 4

Question

Chapter 20, Problem 20.57AP

Interpretation Introduction

(a)

Interpretation:

The structure of optically inactive compound A with the molecular formula C6H10O4 that follows the given NMR data and can be resolved into enantiomers is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Interpretation Introduction

(b)

Interpretation:

The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

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Answer 5

Chapter 20, Problem 20.57AP

Interpretation Introduction

(a)

Interpretation:

The structure of optically inactive compound A with the molecular formula C6H10O4 that follows the given NMR data and can be resolved into enantiomers is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Interpretation Introduction

(b)

Interpretation:

The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Answer 6

Chapter 20, Problem 20.57AP

Interpretation Introduction

(a)

Interpretation:

The structure of optically inactive compound A with the molecular formula C6H10O4 that follows the given NMR data and can be resolved into enantiomers is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Answer 7

Chapter 20, Problem 20.57AP

Interpretation Introduction

(a)

Interpretation:

The structure of optically inactive compound A with the molecular formula C6H10O4 that follows the given NMR data and can be resolved into enantiomers is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.

Concept introduction:

Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.

Answer 10

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Answer 12

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Answer 13

Ch. 20 - Prob. 20.1P Ch. 20 - Prob. 20.2P Ch. 20 - Prob. 20.3P Ch. 20 - Prob. 20.4P Ch. 20 - Prob. 20.5P Ch. 20 - Prob. 20.6P Ch. 20 - Prob. 20.7P Ch. 20 - Prob. 20.8P Ch. 20 - Prob. 20.9P Ch. 20 - Prob. 20.10P

Solution Summary: The author explains the structure of the optically inactive compound A that follows the given NMR data and can be resolved into enantiomers.

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