Advanced pre-university Organic Chemistry:  13C NMR spectrum of 3-hydroxybutanone (acetoin)

Interpreting and explaining the Carbon-13 NMR spectrum of 3-hydroxybutanone  (acetoin)

[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 spectrometry - analysing the 13C NMR spectra of 3-hydroxybutanone [spectra page updated April 3rd 2026 *]

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Introductory note on the 13C NMR spectrum of 3-hydroxybutanone

Students and teachers please note that my explanation of the carbon-13 NMR spectrum of 3-hydroxybutanone is designed for advanced, but pre-university, chemistry courses.

The description does not involve the chemical shift δ spin-spin coupling effects for 3-hydroxybutanone 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 3-hydroxybutanone molecule.

The most common solvent used for investigating the 13C NMR spectrum of compounds like 3-hydroxybutanone, is CDCl3 and other deuterated solvents.

13C nmr spectrum of 3-hydroxybutanone C4H8O2 CH3COCH(OH)CH3 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of acetoin 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 - 3-hydroxybutanone here.

C4H8O2, 3-hydroxybutanone 3-hydroxybutan-2-one acetoin CH3COCH(OH)CH3 C4H8O2, 3-hydroxybutanone, 3-hydroxybutan-2-one, 'acetoin', CH3COCH(OH)CH3

The molecular structure and naming of aliphatic alcohols

The molecular structure and naming of aldehydes and ketones

Interpreting the C-13 NMR spectrum of 3-hydroxybutanone

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

CH3COCH(OH)CH3

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

13C chemical shifts (a) to (d) on the C-13 NMR spectrum diagram for 3-hydroxybutanone.

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


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Links associated with 3-hydroxybutanone

The mass spectrum of 3-hydroxybutanone (3-hydroxybutan-2-one, 'acetoin')

The H-1 spectrum of 3-hydroxybutanone (3-hydroxybutan-2-one, 'acetoin')

The infrared spectrum of 3-hydroxybutanone (3-hydroxybutan-2-one, 'acetoin')

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