Interpreting the carbon-13 C13 NMR spectrum of butan-2-ol

CH₃CH(OH)CH₂CH₃ (2-butanol, sec-butyl alcohol)

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 butan-2-ol

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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 - butan-2-ol here.

Interpreting the C-13 NMR spectrum of butan-2-ol

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

CH₃CH(OH)CH₂CH₃

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

¹³C chemical shifts (a) to (d) on the C-13 NMR spectrum diagram for butan-2-ol.

(a) 22.8 ppm for the CH₃ carbon nearest  the OH group.

(b) 69.3 ppm for the CH carbon nearest (attached) to the OH group.

Note the effect on the C-13 NMR shift of the very electronegative oxygen.

(c) 32.1 ppm for the CH₂ group carbon

(d) 10.0 ppm for the carbon of the CH₃ group farthest from OH group, the smallest chemical shift.

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

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