Advanced Organic Chemistry: Infrared spectrum 1,3,5-trimethylbenzene (mesitylene)

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Interpreting the infrared spectrum of 1,3,5-trimethylbenzene (mesitylene)

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 1,3,5-trimethylbenzene (mesitylene)

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Infrared spectroscopy - spectra index

C9H12 infrared spectrum of 1,3,5-trimethylbenzene wavenumbers cm-1 functional group detection fingerprint pattern identification of mesitylene doc brown's advanced organic chemistry revision notes 

Spectra obtained from a liquid film of 1,3,5-trimethylbenzene (mesitylene). The right-hand part of the of the infrared spectrum of 1,3,5-trimethylbenzene (mesitylene), wavenumbers ~1500 to 400 cm-1 is considered the fingerprint region for the identification of 1,3,5-trimethylbenzene (mesitylene) and most organic compounds. It is due to a unique set of complex overlapping vibrations of the atoms of the molecule of 1,3,5-trimethylbenzene (mesitylene).

structural formula 1,3,5-trimethylbenzene mesitylene molecular structure molecular formula C9H12 C6H3(CH3)3

Interpretation of the infrared spectrum of 1,3,5-trimethylbenzene, mesitylene, C6H3(CH3)3

The most prominent infrared absorption lines of 1,3,5-trimethylbenzene (mesitylene)

Strong absorption at wavenumbers 3080 to 3030 cm-1 due to =C-H aryl C-H stretching vibrations.

Strong C-H stretching vibrations from the alkyl groups (CH2 and CH3) at wavenumbers 2975 to 2845 cm-1.

C=C benzene ring vibrations with peaks close to wavenumbers 1600 and 1500 cm-1.

C-H side-chain alkyl vibrations are observed at wavenumbers 1470 to 1370 cm-1.

Other aryl C-H vibration absorptions occur at wavenumbers 900 to 735 cm-1 characteristic of a 1,3,5-trisubstituted benzene ring.

The absence of other specific functional group bands will show that particular functional group is absent from the 1,3,5-trimethylbenzene (mesitylene) molecular structure.

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