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Advanced Organic Chemistry: Carbon-13 NMR spectrum of propanone

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The Carbon-13 NMR spectrum of propanone (acetone)

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 propanone

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C-13 NMR spectroscopy - spectra index

C-13 nmr spectrum of propanone analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of acetone 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 shifts, called chemical shifts, depend on the individual (electronic) chemical environment of the 13C atoms in an organic molecule - propanone here.

propanone (acetone, dimethyl ketone), C3H6O,  aldehydes and ketones nomenclature (c) doc b, aldehydes and ketones nomenclature (c) doc b, aldehydes and ketones nomenclature (c) doc b , aldehydes and ketones nomenclature (c) doc b

Interpreting the C-13 NMR spectrum of propanone  (acetone)

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

CH3COCH3  or  (CH3)2C=O

(Note the 2 colours indicating the 2 different chemical environments of the carbon atoms in propanone).

Note the big effect on the chemical shift on the carbon atom bonded to the highly electronegative oxygen atom.

The carbon-13 NMR spectra a provides direct evidence of 2 different carbon atom environments in the propanone molecule from 2 different chemical shifts (ppm).


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