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Advanced Organic Chemistry: 13C NMR spectrum of 2-methylpropan-2-ol

Interpreting the C-13 NMR spectrum of 2-methylpropan-2-ol (tert-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 2-methylpropan-2-ol

C4H10O (CH3)3COH C-13 nmr spectrum of 2-methylpropan-2-ol analysis of chemical shifts ppm interpretation of 13C chemical shifts ppm of tert-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 - 2-methylpropan-2-ol here.

2-methylpropan-2-ol   C4H10alcohols 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 2-methylpropan-2-ol

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

(CH3)3COH

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

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

Note, because of the symmetry of the molecule, 3 carbon atoms (of the methyl groups) are all equivalent to each other.

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


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