Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 18, Problem 51P
Interpretation Introduction

Interpretation:

The structure of two isomers that have molecular formula C10H12O is to be predicted.

Concept introduction:

Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations.

Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group.

The value of chemical peaks in NMR depends upon the chemical environment around the hydrogen atom.

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Analyze the 13C-NMR spectrum of C8H9NO given below and draw the structure of the compound.
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The NMR spectra for compound 1 were acquired in a 7.5 mg / 0.6 mL solution ofCDCl3 . The 1H and 13C peaks are also listedbelow. Provide a full analysis of the NMR spectra for compound 1. correct assignment of NMR spectra of both 13C spectra.  correct rationalisation of 13C spectrum1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 9.5 Hz, 1H), 7.56 (ddd, J = 8.5, 7.5, 1.6 Hz, 1H),7.51 (dd, J = 7.5, 1.6 Hz, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.30 (dd, J = 8.5, 7.5 Hz, 1H), 6.45(d, J = 9.5 Hz, 1H).13C NMR (101 MHz, CDCl3) δ 160.79, 154.09, 143.43, 131.85, 127.87, 124.44, 118.86,116.94, 116.74.Note: There are two carbon peaks in the 13C spectrum that are so close together that they are not differentiable at the resolution in this experiment.  you should be able to assign these peaks to one of two carbon atoms in 1.

Chapter 18 Solutions

Organic Chemistry - Standalone book

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