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Advanced Organic Chemistry: Infrared spectrum of phenol

Interpreting the infrared spectrum of phenol

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 phenol

infrared spectrum of phenol C6H6O C6H5OH wavenumbers cm-1 functional group detection fingerprint pattern identification of phenol doc brown's advanced organic chemistry revision notes 

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

PhenolC6H6OC6H5OH, (c) doc b(c) doc b

Interpretation of the infrared spectrum of phenol

The most prominent infrared absorption lines of phenol

The most characteristic absorption band is the broad O-H stretching vibration bands at wavenumbers ~3550 to 3230 cm-1, the breadth is caused by interference of hydrogen bonding interactions, common to all hydrogen bonded molecules with a hydroxyl group.

The intermolecular hydrogen bond C6H5-Oδ--Hδ+ǁǁǁ:Oδ--C6H5 in phenol.

There are C-O stretching vibration absorption bands at wavenumbers 1410 to 1310 and 1230 to 1140 cm-1.

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


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