Advanced Organic Chemistry: Carbon-13 NMR spectrum of 2-methoxypropane

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Interpreting the Carbon-13 NMR spectrum of 2-methoxypropane

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 2-methoxypropane

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C-13 NMR spectroscopy - spectra index

13C nmr spectrum of 2-methoxypropane C4H10O CH3CH(OCH3)CH3 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of methyl isopropyl ether 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 - 2-methoxypropane here.

2-methoxypropane    C4H10    alcohols and ether structure and naming (c) doc b    alcohols and ether structure and naming (c) doc b    alcohols and ether structure and naming (c) doc b

Interpreting the C-13 NMR spectrum of 2-methoxypropane

As you can see from the diagram above there are 3 different chemical shift lines in the C-13 NMR spectrum of 2-methoxypropane indicating 3 different chemical environments of the 4 carbon atoms of 2-methoxypropane.

CH3CH(OCH3)CH3  or  (CH3)2CHOCH3

(Note the 3 different colours indicating the 3 different chemical environments of the 4 carbon atoms in 2-methoxypropane).

13C chemical shifts (a) to (c) on the C-13 NMR spectrum diagram for 2-methoxypropane.

Due to the symmetry of the molecule, the carbon atoms of the methyl groups directly attached to the CH group are equivalent to each other (shown in blue).

Note the decreasing effect on the 13C chemical shift as the carbon atom is further from the more electronegative oxygen atom in 2-methoxypropane.

The carbon-13 NMR spectra provides direct evidence of 3 different carbon atom environments for the 4 carbon atoms in the 2-methoxypropane molecule, deduced from the presence of 3 different 13C NMR chemical shifts (ppm).

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