Advanced Organic Chemistry: 13C NMR spectrum of 2-methylpropanoic acid (CH3)2CHCOOH

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Interpreting and explaining the C-13 NMR spectrum of 2-methylpropanoic acid (isobutyric acid)

[Author © Dr Phil Brown PhD: Doc Brown's advanced level organic chemistry exam revision notes suitable for students of UK A level chemistry courses & US K12 grade 11, grade 12 and AP honors chemistry courses: Molecular spectroscopy analysis of 2-methylpropanoic acid (13C NMR spectra) [spectra page updated April 3rd 2026 *]

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Introductory note on the 13C NMR spectrum of 2-methylpropanoic acid

Students and teachers please note that my explanation of the carbon-13 NMR spectrum of 2-methylpropanoic acid is designed for advanced, but pre-university, chemistry courses.

The description does not involve the chemical shift δ spin-spin coupling effects for 2-methylpropanoic acid and the relative size of the carbon-13 NMR shifts does not give the ratio of the carbon atoms in the different non-equivalent chemical environments of the 2-methylpropanoic acid molecule.

The most common solvent used for investigating the 13C NMR spectrum of compounds like 2-methylpropanoic acid, is CDCl3 and other deuterated solvents.

13C nmr spectrum of 2-methylpropanoic acid C4H8O2 (CH3)2CHCOOH analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of isobutyric acid 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-methylpropanoic acid here.

2-methylpropanoic acid (isobutyric acid), C4H8O2  (c) doc b   (c) doc b   (c) doc b

The molecular structure and naming of carboxylic acids and derivatives

Interpreting the C-13 NMR spectrum of 2-methylpropanoic acid

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

CH3CH(CH3)COOH  or  (CH3)2CHCOOH

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

13C chemical shifts (a) ,(b) and (c) on the C-13 NMR spectrum diagram for 2-methylpropanoic acid.

The two methyl group carbon atoms are equivalent to each other, due to the symmetry of the 2-methylpropanoic acid molecule, and therefore have the same 13C NMR chemical shift.

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

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


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