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Advanced Organic Chemistry: Infrared spectrum of methyl methanoate

Interpreting the infrared spectrum of methyl methanoate (methyl formate)

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 infrared spectra of methyl methanoate

infrared spectrum of methyl methanoate wavenumbers cm-1 functional group detection fingerprint pattern identification of methyl formate doc brown's advanced organic chemistry revision notes 

Spectra obtained from a liquid film of methyl methanoate. The right-hand part of the of the infrared spectrum of methyl methanoate, wavenumbers ~1500 to 400 cm-1 is considered the fingerprint region for the identification of methyl methanoate and most organic compounds. It is due to a unique set of complex overlapping vibrations of the atoms of the molecule of methyl methanoate.

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

Interpretation of the infrared spectrum of methyl methanoate (an aliphatic ester)

The most prominent infrared absorption lines of methyl methanoate

Around wavenumber 2900 cm-1 there are absorptions due to C-H stretching vibrations.

There is a strong absorption band at wavenumbers 1750 to 1735 cm-1 due to the carbonyl group, C=O stretching vibration. - the most characteristic feature of the infrared spectrum of methyl methanoate.

At wavenumbers 1200 to 1180 cm-1 absorptions are due to C-O stretching vibrations characteristic of methanoate esters (formates).

The absence of other specific functional group bands will show that particular functional group is absent from the methyl methanoate molecular structure.
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. No OH band is seen in the infrared spectrum of methyl methanoate.

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 methoxymethane are similar with two 'wide-apart' chemical shift singlet peaks in the integrated proton ratio of 3:1 (meaning 2 different 1H chemical environments).

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

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