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Advanced Organic Chemistry: Carbon-13 NMR spectrum of 1-bromopropane

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The Carbon-13 NMR spectrum of 1-bromopropane

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-bromopropane

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C-13 NMR spectroscopy - spectra index

C3H7Br CH3CH2CH2Br C-13 nmr spectrum of 1-bromopropane analysis of chemical shifts ppm interpretation of 13C chemical shifts ppm of n-propyl bromide 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-bromopropane here.

1-bromopropane, C3H7Br, CH3CH2CH2Br, (c) doc b , (c) doc b

Interpreting the C-13 NMR spectrum of 1-bromopropane

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

CH3CH2CH2Br

(Note the 3 different colours indicating the 3 different chemical environments of the carbon atoms in 1-bromopropane).

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

Note the decreasing effect on the chemical shift as the carbon atom is further from the more electronegative oxygen atom of 1-bromopropane.

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


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