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Advanced Organic Chemistry: Infrared spectrum of methyl 2-hydroxybenzoate

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Interpreting the infrared spectrum of methyl 2-hydroxybenzoate

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 2-hydroxybenzoate (methyl salicylate)

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Infrared spectroscopy - spectra index

infrared spectrum of methyl 2-hydroxybenzoate C8H8O3 wavenumbers cm-1 functional group detection fingerprint pattern identification of methyl salicylate oil of wintergreen doc brown's advanced organic chemistry revision notes  

Spectra obtained from a liquid film of methyl 2-hydroxybenzoate. The right-hand part of the of the infrared spectrum of methyl 2-hydroxybenzoate, wavenumbers ~1500 to 400 cm-1 is considered the fingerprint region for the identification of methyl 2-hydroxybenzoate and most organic compounds. It is due to a unique set of complex overlapping vibrations of the atoms of the molecule of methyl 2-hydroxybenzoate.

C8H8O3, (c) doc b or , methyl 2-hydroxybenzoate (methyl salicylate, 'oil of wintergreen'

Methyl 2-hydroxybenzoate has two functional groups and is both an ester and a phenol.

For more see The molecular structure and naming of carboxylic acids and derivatives

For more see The molecular structure and naming of aromatic compounds

Interpretation of the infrared spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

The most prominent infrared absorption lines of methyl 2-hydroxybenzoate (methyl salicylate)

The O-H stretching vibrations produce a broad band, due to hydrogen bonding, from 3800 to 2600 peak at ~3200 cm-1. The hydrogen bonding can be both intermolecular and intramolecular (mostly the latter, since methyl 2-hydroxybenzoate is a liquid at room temperature).

intermolecular and intramolecular hydrogen bonding in methyl 2-hydroxybenzoate methyl salicylate diagram image oil of wintergreen doc brown's advanced organic chemistry

There are several arene C-H stretching vibrations peaking at 3071 cm-1, ( -H)

The peak at ~2955 cm-1 corresponds to the C-H stretching vibrations of the CH3 group.

The very characteristic carbonyl C=O stretching vibrations peaks at 1680 cm-1.

There are several peaks due to C-O stretching vibrations around 1300 to 1250 and 1150 to 1100 cm-1 (where the O is directly bonded to the benzene ring as in a phenol).

There is also a C-O stretching vibration at ~1200 cm-1 for the C-O of the ester linkage

stretching vibration absorptions of the benzene aromatic ring at ~1600 - 1450 cm-1  

The absence of other specific functional group bands will show that a particular functional group is absent from the methyl 2-hydroxybenzoate molecular structure.

The carbonyl group C=O is clearly distinguished in the spectrum of methyl 2-hydroxybenzoate, but this grouping occurs in many other types of organic compound.


Key words & phrases: isomer of molecular formula C8H8O3 image and diagram explaining the infrared spectrum of methyl 2-hydroxybenzoate, complete infrared absorption spectrum of methyl 2-hydroxybenzoate, comparative spectra of methyl 2-hydroxybenzoate, prominent peaks/troughs for identifying functional groups in the infrared spectrum of methyl 2-hydroxybenzoate, important wavenumber values in cm-1 for peaks/troughs in the infrared spectrum of methyl 2-hydroxybenzoate, revision of infrared spectroscopy of methyl 2-hydroxybenzoate, fingerprint region analysis of methyl 2-hydroxybenzoate, how to identify methyl 2-hydroxybenzoate from its infrared spectrum, identifying organic compounds like methyl 2-hydroxybenzoate from their infrared spectrum, how to analyse the absorption bands in the infrared spectrum of methyl 2-hydroxybenzoate detection of carbonyl phenol functional groups in the methyl 2-hydroxybenzoate molecule example of the infrared spectrum of a molecule like methyl 2-hydroxybenzoate with a ester functional group  interpreting interpretation of the infrared spectrum of methyl 2-hydroxybenzoate shows presence of phenol functional group methyl salicylate


Links associated with methyl 2-hydroxybenzoate

The mass spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

The H-1 NMR spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

The C-13 NMR spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

INDEX of all revision notes on CARBOXYLIC ACIDS and DERIVATIVES

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Infrared spectroscopy index

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