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Advanced Organic Chemistry: Carbon-13 NMR spectrum of 1,3-dioxane

Interpreting the Carbon-13 NMR spectrum of 1,3-dioxane

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 1,3-dioxane

13C nmr spectrum of 1,3-dioxane C4H8O2 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of meta-dioxane 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 - 1,3-dioxane here.

Interpreting the C-13 NMR spectrum of 1,3-dioxane

As you can see from the diagram above there are 3 different chemical shift lines in the C-13 NMR spectrum of 1,3-dioxane indicating 3 different chemical environments of the 4 carbon atoms of 1,3-dioxane.

13C chemical shifts (a) to (c) on the C-13 NMR spectrum diagram for 1,3-dioxane.

The b CH2 carbon atoms are equivalent to each other because of the symmetry of the 1,3-dioxane molecule.

The carbon-13 NMR spectra provides direct evidence of 3 different carbon atom environments for the 4 carbon atoms in the 1,3-dioxane molecule, deduced from the presence of 3 different 13C NMR chemical shifts (ppm).


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