Macroscale and Microscale Organic Experiments
Macroscale and Microscale Organic Experiments
7th Edition
ISBN: 9781305577190
Author: Kenneth L. Williamson, Katherine M. Masters
Publisher: Brooks Cole
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Textbook Question
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Chapter 6, Problem 1Q

Assign the peaks in the 1 H

NMR spectrum of eugenol (Fig. 6.23) to specific protons in the molecule. The OH peak is at 5.1 ppm.

Expert Solution & Answer
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Interpretation Introduction

Interpretation:

The peak in 1H spectrum of eugenol should be assigned.

Concept introduction:

NMR is an analytical method that is utilized to identify the structure of a compound. It determines the framework of carbon-hydrogen bonds present in the compound. 1H NMR is used for the analysis of compounds that contains hydrogen atoms.

Number of signals in the 1H NMR of the compound determines the number of different type of hydrogen atoms present in that compound. The splitting of signals is due to protons that are bonded to the adjacent carbon atoms.

The protons that are present in the different chemical environment are known as non-equivalent protons while the protons that are present in same chemical environment are known as equivalent protons.

Answer to Problem 1Q

Eugenol has 12 different hydrogen atoms. The three hydrogen atom present on the aromatic ring show peak around 6.7ppm and the three vinylic hydrogen atom appear around 56ppm. The three hydrogen atoms of the methoxy group show peak at 3.7ppm and three benzylic hydrogen atoms show peak at 3.3ppm.

Explanation of Solution

The structure of eugenol is as follows:

  Macroscale and Microscale Organic Experiments, Chapter 6, Problem 1Q

Eugenol has 12 different hydrogen atoms. The integration of peaks from right to left is 3:2:2:3:2.

There are two peaks for the three hydrogens around 6.7ppm. These peaks are due to the aromatic hydrogen as the aromatic hydrogen are around 7ppm.

There are two peaks for four hydrogen atoms around 56ppm. The one peak is of the hydrogen atom of OH group while the one peak is for the three vinylic hydrogen atoms.

There are two peaks for six around 34ppm. The three hydrogen atoms of the methoxy group are more deshielded as connected to the oxygen atom and therefore show peak at 3.7ppm. While the three benzylic hydrogen atoms are less deshielded due to the absence of oxygen atom and show peak at 3.3ppm.

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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY