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Advanced Organic Chemistry: Carbon-13 NMR spectrum of 2-chloropropane

The Carbon-13 NMR spectrum of 2-chloropropane

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-chloropropane

C3H7Cl CH3CHClCH3 C-13 nmr spectrum of 2-chloropropane analysis of chemical shifts ppm interpretation of 13C chemical shifts ppm of  isopropyl chloride 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-chloropropane here.

2-chloropropane  C3H7Cl  (c) doc b  (c) doc b  (c) doc b

Interpreting the C-13 NMR spectrum of 2-chloropropane

As you can see from the diagram above there are 2 different chemical shift lines in the C-13 NMR spectrum of 2-chloropropane indicating 2 different chemical environments of the 3 carbon atoms of 2-chloropropane.

CH3CHClCH3

(Note the 2 different colours indicating the 2 different chemical environments of the 3 carbon atoms in 2-chloropropane).

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

Note the decreased effect on the 13C chemical shift as the carbon atom is further from the more electronegative chlorine atom of 2-chloropropane.

The carbon-13 NMR spectra provides direct evidence of 2 different carbon atom environments for the 3 carbon atoms in the 2-chloropropane molecule, deduced from the presence of 2 different 13C chemical shifts (ppm).


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