Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter FRP, Problem 35P
Interpretation Introduction

Interpretation:

The structure of the compound using given spectroscopic data is to be elucidated.

Concept introduction:

NMR data indicates the number and type of protons or carbons present in a compound based on the number of signals obtained in 1H NMR or 13C NMR respectively. 1H NMR signals are often indicated as mutiplet such as doublet, triplets, which indicates the number of protons present on carbons adjacent to that proton. Protons of aromatic rings show signals from 6.5 to 7.5 ppm, those of alkyl group from 0.5 to 1.5 ppm, while alkyl groups adjacent to a carbonyl group or oxygen atom show signals from 2.0 to 3.0 ppm. Alcohol groups show a signal at 2.0 to 3.0 ppm but are always a singlet.

Mass spectra of a compound indicate the molecular ion peak which gives the molecular mass of the compound.

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Thymol (molecular formula C10H14O) is the major component of the oil of thyme. Thymol shows IR absorptions at 3500–3200, 3150–2850, 1621, and 1585 cm−1. The 1H NMR spectrum of thymol is given below. Propose a possible structure for thymol.
Draw the compound.
Given here are 1H-NMR and 13C-NMR spectral data for nine compounds. Each compound shows strong absorption between 1720 and 1700 cm-1 and strong, broad absorption over the region 2500–3300 cm-1. Propose a structural formula for each compound.

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Organic Chemistry

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