Advanced Level Organic pre-university/college Chemistry: The infrared spectrum of benzene C6H6

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Interpreting and explaining the infrared spectrum of benzene C6H6

[Author ©  Dr Phil Brown GRIC, PhD: Doc Brown's advanced level organic chemistry exam revision notes suitable for students of UK A level chemistry courses & US K12 grade 11, grade 12 & AP honors chemistry courses: Molecular spectroscopy of benzene [spectrum page updated RE-EDIT]

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 Infrared spectroscopy - spectra index

Introductory note on the infrared spectrum of benzene

Students and teachers please note my explanation of the infrared spectrum of benzene is designed for advanced, but pre-university, chemistry courses.

Based in the infrared spectrum diagram for benzene, only some of the most prominent peaks for particular bond vibrations are discussed, particularly if benzene has a functional group with a particular characteristic wavenumber peak.

The infrared spectrum of benzene is unique and the whole, or selected wavenumbers, can be used to fingerprint its identity, sometimes analysing a mixture containing benzene or following its change of concentration in a reaction.

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

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

aromatic benzene C6H6, skeletal formula (c) doc b , structural/displayed formula

The molecular structure and naming of aromatic compounds

Interpretation of the spectrum of benzene C6H6

The most prominent infrared absorption lines of benzene

There are characteristic =C-H stretching vibrations peaking at ~3030 to 3080 cm-1

Characteristic benzene ring stretching vibrations peaking at ~1480 cm-1. (moderate C=C absorption) and peaking at ~1800 cm-1 (weak absorption).

(I have also seen the 1480 cm-1 absorption attributed to a -H C-H bending vibration)

Most of the peaks in the fingerprint region are due to C-H vibrations of the C-H bond, but a much simpler fingerprint region than most organic compounds due to the very high symmetry of the benzene molecule.

Benzene has a relatively simple infrared spectra because of the high symmetry of the molecule, six bonds are equivalent to each other and six C-H bonds are equivalent to each other.

The absence of other specific functional group bands will show that particular functional group is absent from the benzene molecular structure.

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