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Advanced Organic Chemistry: Carbon-13 NMR spectrum of methyl propanoate

Interpreting the Carbon-13 NMR spectrum of methyl propanoate (methyl propionate)

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 methyl propanoate

13C nmr spectrum of methyl propanoate C4H8O2 CH3CH2COOCH3 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of methyl propionate 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 - methyl propanoate here.

Methyl propanoate   (methyl propionate)   (c) doc b   (c) doc b   (c) doc b  an ester

Interpreting the C-13 NMR spectrum of methyl propanoate

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

CH3CH2COOCH3

(Note the 4 different colours indicating the 4 different chemical environments of the 4 carbon atoms in methyl propanoate).

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

Note the decreasing effect on the 13C chemical shift as the carbon atom is further from the more electronegative oxygen atoms in methyl propanoate.

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


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