Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 20, Problem 20.59AP
Interpretation Introduction

(a)

Interpretation:

The structure of the compound with the molecular formula C9H10O3 that follows the given NMR data and IR data 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 the compound with the molecular formula C9H10O3 that follows the given NMR data and IR data 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

(c)

Interpretation:

The structure of the compound that follows the given NMR data, IR data, UV data, and mass spectrum data 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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Compound C has the molecular formula C5H8O. The IR, 1H, 13C, and DEPT NMR spectra of this compound are shown below. (a) Calculate the double bond equivalent of compound C and briefly explain what the values obtains represents. Interpret the IR spectrum. (b) Based on the information provided, determine the structure of compound D.
(a) The 'H-NMR spectrum of cyclobutanone shows two signals - signal A at 3.00 ppm and signal B at 1.95 ppm. Give the multiplicity of each signal. cyclobutanone (b) When cyclobutanone is treated with D20 and NaOD, the only signal observable in the 1H-NMR is a singlet at 2.00 ppm. Explain why this is the case. [Note: Deuterium atoms do not display signals in the TH-NMR spectrum]
(a) Compound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning. (b) Compound B has molecular formula C8H6O2. The IR, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning. (c) Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for C and explain your reasoning.
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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY