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

Interpreting the Carbon-13 NMR spectrum of ethyl methanoate (ethyl formate)

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 ethyl methanoate

13C nmr spectrum of ethyl methanoate C3H6O2 HCOOCH2CH3 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of ethyl 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 - ethyl methanoate here.

Ethyl methanoate (ethyl formate) C3H6O2  (c) doc b  (c) doc b  (c) doc b  (c) doc b

Interpreting the C-13 NMR spectrum of ethyl methanoate

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

HCOOCH2CH3 

(Note the 3 different colours indicating the 3 different chemical environments of the 3 carbon atoms in ethyl methanoate).

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

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

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


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