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Advanced Organic Chemistry: Carbon-13 NMR spectrum of chlorobenzene

The Carbon-13 NMR spectrum of chlorobenzene

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 chlorobenzene

C6H5Cl C-13 nmr spectrum of chlorobenzene analysis of chemical shifts ppm interpretation of 13C chemical shifts ppm of chlorobenzene 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 shifts, called chemical shifts, depend on the individual (electronic) chemical environment of the 13C atoms in an organic molecule - chlorobenzene here.

chlorobenzene, C6H5Cl, (c) doc b 

Interpreting the C-13 NMR spectrum of chlorobenzene

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

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

These are all due to the benzene ring (no side-chain carbons).

Very high resolution spectrum sorts them out.

13C resonance (a) is for ring carbon atom 4, 126.4 ppm.

13C resonance (b) is for ring carbon atoms 3 and 5, 129.7 ppm.

13C resonance (c) is for ring carbon atoms 2 and 6, 128.6 ppm.

13C resonance (d) is for ring carbon atom 1, 134.3 ppm.

The carbon-13 NMR spectra a provides direct evidence of 4 different carbon atom environments of the 6 carbon atoms of the chlorobenzene molecule from 4 different 13C chemical shifts (ppm).


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