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Advanced Organic Chemistry: H-1 NMR spectrum of ethyl ethanoate

H-1 hydrogen-1 (proton) NMR spectrum of ethyl ethanoate (ethyl acetate)

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 ethyl ethanoate

low and high resolution H-1 proton nmr spectrum of ethyl ethanoate analysis interpretation of chemical shifts ppm spin spin line splitting of ethyl acetate diagram 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 - ethyl ethanoate here.

The chemical shifts quoted in ppm on the diagram of the H-1 NMR spectrum of ethyl ethanoate 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 ethyl ethanoate molecule.

Ethyl ethanoate C4H8O2  (c) doc b , (c) doc b , (c) doc b , (c) doc b 

Interpreting the H-1 NMR spectrum of ethyl ethanoate

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

The hydrogen atoms (protons) of ethyl ethanoate occupy three different chemical environments so that the H-1 proton low resolution NMR spectra should show 3 peaks (diagram above for ethyl ethanoate).

ethyl ethanoate (c) doc b ,(c) doc b ,(c) doc b ,(c) doc b

CH3COOCH2CH3

Note the ratio 3:2:3 of the three colours of the protons in the three chemically different environments.

Although there are 8 hydrogen atoms in the molecule, there only 3 possible chemical environment for the hydrogen atoms in ethyl ethanoate molecule.

The proton ratio of 3:2:3 observed, corresponds with the structural formula of ethyl ethanoate.

The high resolution spectrum of ethyl ethanoate

So, using the chemical shifts and applying the n+1 rule to ethyl ethanoate

At 0.92 ppm the CH2 protons split the 'right-hand' CH3 shift into 1:2:1 triplet.

Evidence of the CH2 group in the molecule of ethyl ethanoate

At 2.04 ppm the 'left-hand' CH3 protons show no evident splitting shift by adjacent protons

Evidence that one of the CH3 groups is not joined to another carbon atom with protons - as is the case with ethyl ethanoate molecule.

The proton ratio in the spectrum allows the deduction of two methyl groups in the molecule.

At 4.10 ppm the CH2 proton line is split into a 1:3:3:1 quartet by the adjacent methyl group.

Evidence that there is indeed another CH3 group joined to another carbon atom with protons - as is the case with ethyl ethanoate 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: proton nmr of ethyl acetate Interpreting the proton H-1 NMR spectra of ethyl ethanoate, low resolution & high resolution proton nmr spectra of ethyl ethanoate, H-1 nmr spectrum of ethyl ethanoate, understanding the hydrogen-1 nmr spectrum of ethyl ethanoate, explaining the line splitting patterns in the high resolution H-1 nmr spectra of ethyl ethanoate, revising the H-1 nmr spectrum of ethyl ethanoate, proton nmr of ethyl ethanoate, ppm chemical shifts of the H-1 nmr spectrum of ethyl ethanoate, 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 ethyl ethanoate, how to work out the number of chemically different protons in the structure of the ethyl ethanoate organic molecule, how to analyse the chemical shifts in the hydrogen-1 H-1 proton NMR spectrum of ethyl ethanoate using the n+1 rule to explain the spin - spin coupling ine splitting in the proton nmr spectrum of ethyl ethanoate deducing the nature of the protons from the chemical shifts ppm in the H-1 nmr spectrum of ethyl ethanoate


Links associated with ethyl ethanoate

The chemistry of CARBOXYLIC ACIDS and DERIVATIVES revision notes INDEX

H-1 proton NMR spectroscopy index  (Please read 8 points at the top of the 1H NMR index page)

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