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Advanced Organic Chemistry: Carbon-13 NMR spectrum of propyl methanoate

Interpreting the Carbon-13 NMR spectrum of propyl methanoate

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 propyl methanoate

13C nmr spectrum of propyl methanoate C4H8O2 HCOOCH2CH2CH3 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of propyl formate 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 - propyl methanoate here.

Propyl methanoate (propyl formate)   (c) doc b    (c) doc b    (c) doc b 

Interpreting the C-13 NMR spectrum of propyl methanoate

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

HCOOCH2CH2CH3

(Note the 4 different colours indicating the 4 different chemical environments of the 4 carbon atoms in propyl methanoate).

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

Note the decreasing effect on the 13C chemical shift as the carbon atom is further from the more electronegative oxygen atoms in the propyl group of propyl methanoate.

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


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