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Advanced Organic Chemistry: Carbon-13 NMR spectrum of 3-hydroxybutanone

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

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 3-hydroxybutanone

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

Interpreting the C-13 NMR spectrum of 3-hydroxybutanone

As you can see from the diagram above there are 4 different 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 chemistry of ALCOHOLS revision notes INDEX

The chemistry of ALDEHYDES and KETONES revision notes INDEX

C-13 NMR spectroscopy index

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