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Advanced Organic Chemistry: Infrared spectrum of methyl ethanoate

Interpreting the infrared spectrum of methyl ethanoate (methyl 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 infrared spectra of methyl ethanoate

infrared spectrum of methyl ethanoate C3H6O2 CH3COOCH3 wavenumbers cm-1 functional group detection fingerprint pattern identification of methyl acetate doc brown's advanced organic chemistry revision notes 

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

methyl ethanoate (methyl acetate), (c) doc b,(c) doc b , (c) doc b, (c) doc b

Interpretation of the infrared spectrum of methyl ethanoate

The most prominent infrared absorption lines of methyl ethanoate

C-H stretching vibration absorptions occur in the wavenumber region 2975 to 2860 cm-1.

Not very important, common to most organic molecules.

For saturated aliphatic esters, C=O stretching vibration absorptions occur in the wavenumber region 1750 to 1735 cm-1.

This is a very characteristic absorption for any molecule e.g. an ester, with a carbonyl group.

For ethanoate esters, C-O stretching vibration absorptions occur in the wavenumber region 1250 to 1230 cm-1.

The absence of other specific functional group bands will show that a particular functional group is absent from the methyl ethanoate molecular structure e.g. no hydroxyl group vibration, a wide band at ~3500 to 2500 cm-1, obviously not expected for an ester like methyl ethanoate, but expected for a carboxylic acid like the isomeric propanoic acid.


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