fun, you could cover them and make sure that you could draw them). Dut the five following sets of data, A-E, consisting of infrared and 'H and 13C NMR spectra. You may find it helpful to draw or redraw them showing the hydrogens explicitly, and/or to determine the number of types of H's and C's.

Principles of Instrumental Analysis
7th Edition
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Chapter19: Nuclear Magnetic Resonance Spectroscopy
Section: Chapter Questions
Problem 19.23QAP
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Objectives:
To use spectroscopic data to identify organic molecules
To predict infrared and 'H and 13C NMR spectroscopic data for organic molecules.
Through the above, to gain comfort with spectroscopy and mass spectrometry as they are used in modem organic chemistry.
1. The skeletal structures for a set of seven C4H10 alcohols and ethers are provided below (although just for
fun, you could cover them and make sure that you could draw them!). Determine which of the seven compounds matches with each of
the five following sets of data, A-E, consisting of infrared and 'H and 13C NMR spectra. You may find it helpful to draw or redraw them
showing the hydrogens explicitly, and/or to determine the number of types of H's and C's.
On the page of each data set, draw the structure of the corresponding molecule with the data, and indicate, for each
spectrum, what about those data is important in determining that the correct molecule has been chosen. In the case of the IR spectrum,
cite absorbance bands that are present (or absent). For the 13C NMR spectrum and 'H NMR spectrum
describe how the number of signals and their chemical shifts fit the structure chosen. For the 'H spectrum, also do the same with the
data from integration of the signals and their multiplicity.
Structures of the four alcohols and three ethers:
OH
TOH
to
OH
Дон
Transcribed Image Text:Objectives: To use spectroscopic data to identify organic molecules To predict infrared and 'H and 13C NMR spectroscopic data for organic molecules. Through the above, to gain comfort with spectroscopy and mass spectrometry as they are used in modem organic chemistry. 1. The skeletal structures for a set of seven C4H10 alcohols and ethers are provided below (although just for fun, you could cover them and make sure that you could draw them!). Determine which of the seven compounds matches with each of the five following sets of data, A-E, consisting of infrared and 'H and 13C NMR spectra. You may find it helpful to draw or redraw them showing the hydrogens explicitly, and/or to determine the number of types of H's and C's. On the page of each data set, draw the structure of the corresponding molecule with the data, and indicate, for each spectrum, what about those data is important in determining that the correct molecule has been chosen. In the case of the IR spectrum, cite absorbance bands that are present (or absent). For the 13C NMR spectrum and 'H NMR spectrum describe how the number of signals and their chemical shifts fit the structure chosen. For the 'H spectrum, also do the same with the data from integration of the signals and their multiplicity. Structures of the four alcohols and three ethers: OH TOH to OH Дон
Spectra B
5000
overlapping
t, s
200
180 160 140
120
100
80
60
40
20
ppm
11
10
ppm
H
4000
3000
2000
1500
1000
500
Wavenumbers, cm*1
Structure:
IR:
13C NMR:
Number of types of C:
Chemical shift(s) of signals:
'H NMR:
Number of types of H:
⚫ Chemical shift(s) of signals:
• Integrations:
• Multiplicity of peaks:
sextet t
Transcribed Image Text:Spectra B 5000 overlapping t, s 200 180 160 140 120 100 80 60 40 20 ppm 11 10 ppm H 4000 3000 2000 1500 1000 500 Wavenumbers, cm*1 Structure: IR: 13C NMR: Number of types of C: Chemical shift(s) of signals: 'H NMR: Number of types of H: ⚫ Chemical shift(s) of signals: • Integrations: • Multiplicity of peaks: sextet t
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