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Advanced Organic Chemistry: Carbon-13 NMR spectrum of butan-2-ol  (2-butanol)

Interpreting the C13 NMR spectrum of butan-2-ol  (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

C4H10O CH3CH(OH)CH2CH3 C-13 nmr spectrum of butan-2-ol analysis of chemical shifts ppm interpretation of 13C chemical shifts ppm of 2-butanol sec-butyl alcohol 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 - butan-2-ol here.

Butan-2-ol    C4H10O    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 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.

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).


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