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Advanced Organic Chemistry: Carbon-13 NMR spectrum of benzaldehyde

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The Carbon-13 NMR spectrum of benzaldehyde

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 benzaldehyde

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C-13 NMR spectroscopy - spectra index

C7H6O C6H5CHO C-13 nmr spectrum of benzaldehyde analysis of chemical shifts ppm interpretation of 13C chemical shifts ppm of benzaldehyde 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 - benzaldehyde here.

 benzaldehyde C7H6O, C6H5CHO , (c) doc b , (c) doc b 

Interpreting the C-13 NMR spectrum of benzaldehyde

As you can see from the diagram above there are 5 different chemical shift lines in the C-13 NMR spectrum of benzaldehyde indicating 5 different chemical environments of the carbon atoms.

Chemical shifts (a) to (d) on the C-13 NMR spectrum diagram for benzaldehyde.

13C resonance (a) is for benzene ring carbon 4, chemical shift 134.4 ppm.

13C resonance (b) is for benzene ring carbons 3 and 5, chemical shift 129.0 ppm.

13C resonance (c) is for benzene ring carbons 2 and 6, chemical shift 129.7 ppm.

13C resonance (d) is for benzene ring carbon 1, chemical shift 136.5 ppm.

13C resonance (e) is for the carbon atom of the aldehyde group, chemical shift 192.3 ppm - significantly higher than the closely 'packed' benzene ring carbon atom resonances.

The carbon-13 NMR spectra a provides direct evidence of 5 different carbon atom environments for the 7 carbon  atoms in the benzaldehyde molecule, deduced from 5 different 13C chemical shifts (ppm).


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