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Advanced Organic Chemistry: Carbon-13 NMR spectrum of phenol

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Interpreting the Carbon-13 NMR 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 C-13 NMR spectra of phenol

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C-13 NMR spectroscopy - spectra index

13C nmr spectrum of phenol C6H6O C6H5OH analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of phenol C13 13-C nmr doc brown's advanced organic chemistry revision notes 

TMS is the acronym for tetramethylsilane, formula Si(CH3)4, whose 13C atoms are arbitrarily given a chemical shift of 0.0 ppm. This is the 'standard' in 13C NMR spectroscopy and all other 13C resonances, called chemical shifts, are measured with respect to the TMS, and depend on the individual (electronic) chemical environment of the 13C atoms in an organic molecule - phenol here.

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

Interpreting the C-13 NMR spectrum of phenol

As you can see from the diagram above there are 4 different chemical shift lines in the C-13 NMR spectrum of phenol indicating 4 different chemical environments of the 6 carbon atoms of phenol.

13C chemical shifts (a) to (d) on the C-13 NMR spectrum diagram for phenol.

aromatic benzene ring carbon atom positions in phenol 13C NMR spectroscopy Numbering of benzene ring carbon atoms.

As a consequence of the symmetry of phenol:

Resonance (b) is for the equivalent carbon atoms 2 and 6.

Resonance (c) is for the equivalent carbon atoms 3 and 5.

Carbon atoms 1 and 4 are not equivalent to any other carbon atoms in the benzene ring.

The carbon-13 NMR spectra provides direct evidence of 4 different carbon atom environments for the 6 carbon atoms in the phenol molecule, deduced from the presence of 4 different 13C NMR chemical shifts (ppm).


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