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Advanced Organic Chemistry: H-1 NMR spectrum of methyl methanoate

The H-1 hydrogen-1 (proton) NMR spectrum of methyl methanoate

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 methyl methanoate

See also comparing the infrared, mass, 1H and 13C NMR spectra of the isomers of C2H4O2

low and high resolution H-1 proton nmr spectrum of methyl methanoate analysis interpretation of chemical shifts ppm spin spin line splitting diagram H1 1-H nmr for methyl formate 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 - methyl methanoate here.

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

Methyl methanoate (methyl formate) C2H4O2(c) doc b , (c) doc b , (c) doc b

For more see Structure and naming of CARBOXYLIC ACIDS and DERIVATIVES, including isomers

Interpreting the H-1 NMR spectrum of methyl methanoate

For relatively simple molecules, the low or high resolution H-1 NMR spectrum of methyl methanoate shows two peaks (diagram above).

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

HCOOCH3

Note the ratio 1:3 of the two colours of the protons in the two chemically different environments

Although there are four hydrogen atoms in the molecule, there only 2 possible chemical environments for the hydrogen atoms in methyl methanoate molecule.

The integrated proton ratio integrated 1:3 ratio observed, corresponds with the structural formula of methyl methanoate.

The two 1H chemical environments in the methyl methanoate molecule are the methyl group protons (CH3, 3.75 ppm chemical shift) and the CH proton (8.07 ppm chemical shift).

Neither proton resonance signal is split because there are no protons on an adjacent carbon atom, the carbon atoms/protons are separated by an oxygen atom.


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

Comparing the infrared, mass, 1H NMR and 13C NMR spectra of the 2 isomers of C2H4O2

NOTE: The images are linked to their original detailed spectral analysis pages AND can be doubled in size with touch screens to increase the definition to the original ethanoic acid (acetic acid) and methyl methanoate (methyl formate) image sizes.

INFRARED SPECTRA: Apart from the significant differences in the fingerprint region at wavenumbers 1500 to 400 cm-1, the most striking difference is the broad O-H stretching band ~3200 cm-1, found in the infrared spectrum of carboxylic acids, but absent in the infrared spectrum of esters.

MASS SPECTRA: Apart from the m/z of 60 for the parent molecular ion and m/z 15 ion [CH3]+, both ethanoic acid and methyl methanoate show few similarities in their mass spectra. Their base ion peaks are quite different - for ethanoic acid it is m/z 43 and for methyl methanoate it is m/z 31.

1H NMR SPECTRA: The 1H NMR spectra of ethanoic acid and methyl methanoate are similar with two 'wide-apart' chemical shift singlet peaks in the integrated proton ratio of 3:1 (meaning 2 different 1H chemical environments). However, although no splitting is observed, the 1H chemical shifts for the two molecules are different, those of methyl methanoate are much closer together.

13C NMR SPECTRA: The 13C NMR spectra of ethanoic acid and methyl methanoate are similar, both molecules give two C-13 NMR spectral lines (meaning 2 different 13C chemical environments).


Key words & phrases: methyl formate Interpreting the proton H-1 NMR spectra of methyl methanoate, low resolution & high resolution proton nmr spectra of methyl methanoate, H-1 nmr spectrum of methyl methanoate, understanding the hydrogen-1 nmr spectrum of methyl methanoate, explaining the line splitting patterns in the high resolution H-1 nmr spectra of methyl methanoate, revising the H-1 nmr spectrum of methyl methanoate, proton nmr of methyl methanoate, ppm chemical shifts of the H-1 nmr spectrum of methyl methanoate, 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 methyl methanoate, how to work out the number of chemically different protons in the structure of the methyl methanoate organic molecule, how to analyse the chemical shifts in the hydrogen-1 H-1 proton NMR spectrum of methyl methanoate using the n+1 rule to explain the spin - spin coupling ine splitting in the proton nmr spectrum of methyl methanoate deducing the nature of the protons from the chemical shifts ppm in the H-1 nmr spectrum of methyl methanoate examining the 1H nmr spectrum of  methyl methanoate analysing the 1-H nmr spectrum of methyl methanoate how do you sketch and interpret the H-1 NMR spectrum of methyl methanoate interpreting interpretation of the H-1 proton NMR spectrum of methyl methanoate methyl formate

Molecular structure diagram of the proton NMR diagram for the 1H NMR spectrum of methyl methanoate. The proton ratio in the 1H NMR spectrum of methyl methanoate. Deducing the number of different chemical environments of the protons in the methyl methanoate molecule from the 1H chemical shifts in the hydrogen-1 NMR spectrum of methyl methanoate. Analysing the high resolution 1H NMR spectrum of methyl methanoate. Analysing the low resolution 1H NMR spectrum of methyl methanoate. You may need to know the relative molecular mass of methyl methanoate to deduce the molecular formula from the proton ratio of the 1H NMR spectrum of methyl methanoate. Revision notes on the proton NMR spectrum of methyl methanoate. Matching and deducing the structure of the methyl methanoate molecule from its hydrogen-1 NMR spectrum. Proton NMR spectroscopy of esters, 1H NMR spectra of methyl methanoate, an isomer of molecular formula C2H4O2


Links associated with methyl methanoate

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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