13C nmr spectrum of cyclohexene C6H10 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of cyclohexene C13 13-C nmr carbon-13 doc brown's advanced organic chemistry revision notes

Advanced Organic Chemistry: Carbon-13 NMR spectrum of cyclohexene

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Interpreting the Carbon-13 13C NMR spectrum of cyclohexene

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 cyclohexene

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C-13 NMR spectroscopy - spectra index

13C nmr spectrum of cyclohexene C6H10 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of cyclohexene C13 carbon-13 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 - cyclohexene here.

cyclohexene , , alkenes structure and naming (c) doc b ,

Interpreting the C-13 NMR spectrum of cyclohexene

As you can see from the diagram above there are 3 different chemical shift lines in the C-13 NMR spectrum of cyclohexene indicating 3 different chemical environments of the 10 carbon atoms of cyclohexene.

¹³C chemical shifts δ (a) to (c) on the C-13 NMR spectrum diagram for cyclohexene.

(a) structure : ¹³C NMR chemical shift δ of 22.8 ppm

The ¹³C NMR resonance for the 2 x equivalent C atoms furthest from the C=C bond.

(b) structure : ¹³C NMR chemical shift δ of 25.3 ppm

The ¹³C NMR resonance for the 2 x equivalent C atoms nearest to the C=C bond.

(c) structure : ¹³C NMR chemical shift δ of 127.3 ppm

The ¹³C NMR resonance for the 2 x equivalent C atoms of the actual C=C bond itself.

The presence of the pi electron cloud produces the largest chemical shift for the C=C bond carbons compared to the other two.

The carbon-13 NMR spectra provides direct evidence of 3 different carbon atom environments for the 10 carbon atoms in the cyclohexene molecule, deduced from the presence of 3 different 13C NMR chemical shifts (ppm).

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