Advanced Organic Chemistry: Carbon-13 NMR spectrum of 1-methylethyl methanoate

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Interpreting the Carbon-13 NMR spectrum of 1-methylethyl 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 1-methylethyl methanoate

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C-13 NMR spectroscopy - spectra index

13C nmr spectrum of 1-methylethyl methanoate C4H8O2 HCOOCH(CH3)2 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of isopropyl 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 - 1-methylethyl methanoate here.

HCOOCH(CH3)2  1-methylethyl methanoate, propan-2-yl methanoate,

is an example of an ester, some old names: isopropyl methanoate, isopropyl formate

Interpreting the C-13 NMR spectrum of 1-methylethyl methanoate

As you can see from the diagram above there are 3 different chemical shift lines in the C-13 NMR spectrum of 1-methylethyl methanoate indicating 3 different chemical environments of the 4 carbon atoms of 1-methylethyl methanoate.

HCOOCH(CH3)2

(Note the 3 different colours indicating the 3 different chemical environments of the4 carbon atoms in 1-methylethyl methanoate).

13C chemical shifts (a) to (c) on the C-13 NMR spectrum diagram for 1-methylethyl methanoate.

The methyl group carbon atoms are equivalent to each other due to the symmetry of the 1-methl methanoate molecule.

Note the decreasing effect on the 13C chemical shift as the carbon atom of the alkyl group is further from the more electronegative oxygen atoms in 1-methylethyl methanoate.

The carbon-13 NMR spectra provides direct evidence of 3 different carbon atom environments for the 4 carbon atoms in the 1-methylethyl methanoate molecule, deduced from the presence of 4 different 13C NMR chemical shifts (ppm).

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