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Advanced Organic Chemistry: H-1 NMR spectrum of ethoxyethane

The H-1 hydrogen-1 (proton) NMR spectrum of ethoxyethane (diethyl ether)

Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK IB KS5 A/AS GCE advanced A level organic chemistry students US K12 grade 11 grade 12 organic chemistry courses involving molecular spectroscopy analysing H-1 NMR spectra of ethoxyethane

low and high resolution H-1 proton nmr spectrum of ethoxyethane analysis interpretation of chemical shifts ppm spin spin line splitting diagram of  diethyl ether doc brown's advanced organic chemistry revision notes

TMS is the acronym for tetramethylsilane, formula Si(CH3)4, whose protons are arbitrarily given a chemical shift of 0.0 ppm. This is the 'standard' in 1H NMR spectroscopy and all other proton shifts, called chemical shifts, depend on the individual (electronic) chemical environment of the hydrogen atoms in an organic molecule - ethoxyethane here.

The chemical shifts quoted in ppm on the diagram of the H-1 NMR spectrum of ethoxyethane represent the peaks of the intensity of the chemical shifts of (which are often groups of split lines at high resolution) AND the relative integrated areas under the peaks gives you the ratio of protons in the different chemical environments of the ethoxyethane molecule.

Ethoxyethane C4H10O, alcohols and ether structure and naming (c) doc b , alcohols and ether structure and naming (c) doc b , alcohols and ether structure and naming (c) doc b

Interpreting the H-1 NMR spectrum of ethoxyethane (diethyl ether)

For relatively simple molecules, the low resolution H-1 NMR spectrum of ethoxyethane is a good starting point.

The hydrogen atoms (protons) of ethoxyethane occupy 2 different chemical environments so that the H-1 proton low resolution NMR spectra should show 2 peaks (diagram above).

CH3CH2OCH2CH3

(note the ratio of the 2 colours of the protons in ethoxyethane, 6 : 4  or  3 : 2)

So, although there are 10 hydrogen atoms in the molecule there are only 2 possible chemical environment for the hydrogen atoms.

The proton ratio observed 3 : 2, corresponds with the structural formula of ethoxyethane (6 : 4).

The high resolution spectrum of ethoxyethane is far more complex.

So, applying the n+1 rule:

At the chemical shift of 1.21, the CH3 protons are split into a 1 : 2 : 1 triplet by the CH2 protons.

This is evidence for the presence of a CH2 group in the ethoxyethane molecule.

At the chemical shift of 3.47, the CH2 protons are split into a 1 : 3 : 3 : 1 quartet by the CH3 protons.

This is evidence of a CH3 group in the ethoxyethane molecule.


Number of protons 1H causing splitting Splitting pattern produced from the n+1 rule and the theoretical ratio of line intensities
0 means no splitting             1            
1 creates a doublet           1   1          
2 creates a triplet         1   2   1        
3 creates a quartet       1   3   3   1      
4 creates a quintet     1   4   6   4   1    
5 creates a sextet   1   5   10   10   5   1  
6 creates a septet 1   6   15   20   15   6   1

Key words & phrases: Interpreting the proton H-1 NMR spectra of ethoxyethane, low resolution & high resolution proton nmr spectra of ethoxyethane, H-1 nmr spectrum of ethoxyethane, understanding the hydrogen-1 nmr spectrum of ethoxyethane, explaining the line splitting patterns in the high resolution H-1 nmr spectra of ethoxyethane, revising the H-1 nmr spectrum of ethoxyethane, proton nmr of ethoxyethane, ppm chemical shifts of the H-1 nmr spectrum of ethoxyethane, explaining and analyzing spin spin line splitting in the H-1 nmr spectrum, how to construct the diagram of the H-1 nmr spectrum of ethoxyethane, how to work out the number of chemically different protons in the structure of the ethoxyethane organic molecule, how to analyse the chemical shifts in the hydrogen-1 H-1 proton NMR spectrum of ethoxyethane diethyl ether


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