EBK A SMALL SCALE APPROACH TO ORGANIC L
EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN: 9781305446021
Author: Lampman
Publisher: CENGAGE LEARNING - CONSIGNMENT
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Chapter 14, Problem 1Q
Interpretation Introduction

Interpretation:

The infrared spectra for carvone and limonene needs to be interpreted. Also, the proton and carbon-13 NMR spectra of carvone needs to be explained.

Concept Introduction:

In the IR spectroscopy, the IR region of the electromagnetic spectrum is studied. Here, light has a longer wavelength than the visible light. In this, the interaction of molecules with the IR light is studied.

Nuclear Magnetic Resonance (NMR) spectroscopy is a logical chemistry method used in quality control.

It studies for defining the material and purity of a sample and their molecular structure. It explains magnetic energy levels undergoing the resonance transition when the atomic nuclei are exposed to an external magnetic field and an electromagnetic radiation is applied with the specific frequency. The NMR spectrum is obtained by detecting the absorption signals.

Expert Solution & Answer
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Explanation of Solution

The structure of limonene is represented as follows:

  EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 14, Problem 1Q , additional homework tip  1

Limonene will have C-H stretching at 3000 cm-1 and C=C stretching at 1645 cm-1

Now, the structure of Carvone is represented as follows:

  EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 14, Problem 1Q , additional homework tip  2

Carvone will have C=C stretching at 1645 cm-1 and a, β-unsaturated ketone will have stretching at 1672 cm-1.

The structures of Carvone are given below along with the NMR interpretation (both 1H and 13C).

  EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 14, Problem 1Q , additional homework tip  3

Carvone NMR (1H and 13C)

In the NMR of Carvone two methyl peaks are there along with vinylic protons. There are few CH2 protons. In 13-C there are a, β-unsaturated ketone peak along with C=C peaks. Two methyl peaks and CH2 peaks.

In NMR of limonene there are two methyl peaks, few CH2 peaks and vinylic protons. In 13-C there are two methyl along with C=C and CH2 peaks.

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