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Advanced Organic Chemistry: Carbon-13 NMR spectrum of 3-ethylpentane

The Carbon-13 NMR spectrum of 3-ethylpentane

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 3-ethylpentane

See also comparing the 1H NMR and 13C NMR spectra of the nine alkane structural isomers of C7H16

C7H16 C-13 nmr spectrum of 3-ethylpentane analysis of chemical shifts ppm interpretation of 13C chemical shifts ppm of 3-ethylpentane 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 - 3-ethylpentane here.

3-ethylpentane alkanes structure and naming (c) doc b alkanes structure and naming (c) doc b alkanes structure and naming (c) doc b alkanes structure and naming (c) doc b

For more see The molecular structure, classification and naming of alkanes

Interpreting the C-13 NMR spectrum of 3-ethylpentane

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

(CH3CH2)3CH

(Note the 3 different colours indicating the 3 different chemical environments of the 7 carbon atoms in 3-ethylpentane).

Chemical shifts (a) to (c) on the C-13 NMR spectrum diagram for 3-ethylpentane.

The higher symmetry of the 3-ethylpentane molecules reduces the chemical environments of the protons compared to seven of the other isomers of C7H16. (see comparison table below)

The carbon-13 NMR spectra a provides direct evidence of 3 different carbon atom environments for the 7 carbon atoms in the 3-ethylpentane molecule, deduced from the presence of 3 different 13C chemical shifts (ppm).

Comparing the 1H NMR and 13C NMR spectra of the nine alkane structural isomers of C7H16

You can distinguish all 9 isomers from a data combination of their number of 1H NMR chemical shifts,

and their resulting integrated 1H proton ratios, plus, their number of 13C chemical shifts.

Name of the alkane structural isomer of molecular formula C7H16 Abbreviated structural formulae of the nine isomers of molecular formula C7H16 (interpretation complications with 3-methylhexane and 2,3-dimethylpentane because they exhibit R/S isomerism due to a chiral carbon) Skeletal formula of the nine alkane isomers of  molecular formula C7H16 Number of 1H NMR chemical shifts (δ) and proton ratio (links to spectrum) Number of 13C chemical shifts (δ) (links to spectrum)
heptane structural formula skeletal formula alkanes molecular structure naming (c) doc b heptane skeletal formula alkanes molecular structure naming (c) doc b 4 δ: proton ratio: 3:2:2:1 (6:4:4:2 in the molecule) 4 δ shifts
2-methylhexane structural formula skeletal formula alkanes molecular structure naming (c) doc b 2-methylhexane skeletal formula alkanes molecular structure naming (c) doc b 6 δ: proton ratio : 6:3:2:2:2:1 6 δ shifts
3-methylhexane structural formula skeletal formula alkanes molecular structure naming (c) doc b 3-methylhexane skeletal formula alkanes molecular structure naming (c) doc b 7 δ: proton ratio: 3:3:3:2:2:2:1 (simplification) !!! 7 δ shifts
3-ethylpentane structural formula skeletal formula alkanes molecular structure naming (c) doc b 3-ethylpentane skeletal formula alkanes molecular structure naming (c) doc b 3 δ: proton ratio: 9:6:1 3 δ shifts
2,2-dimethylpentane structural formula skeletal formula alkanes molecular structure naming (c) doc b 2,2-dimethylpentane skeletal formula alkanes molecular structure naming (c) doc b 4 δ: proton ratio: 9:3:2:2 5 δ shifts
2,3-dimethylpentane structural formula skeletal formula alkanes molecular structure naming (c) doc b 2,3-dimethylpentane skeletal formula alkanes molecular structure naming (c) doc b 6 δ: proton ratio: 6:3:3:2:1:1 (simplification) !!! 6 δ shifts (simplification) !!!
2,4-dimethylpentane structural formula skeletal formula alkanes molecular structure naming (c) doc b 2,4-dimethylpentane skeletal formula alkanes molecular structure naming (c) doc b 3 δ: proton ratio: 12:2:2 3 δ shifts
3,3-dimethylpentane structural formula skeletal formula alkanes molecular structure naming (c) doc b 3,3-dimethylpentane skeletal formula alkanes molecular structure naming (c) doc b 3 δ: proton ratio: 3:3:2 (6:4:4 in the molecule) 4 δ shifts
2,2,3-trimethylbutane structural formula skeletal formula alkanes molecular structure naming (c) doc b 2,2,3-trimethylbutane skeletal formula alkanes molecular structure naming (c) doc b 3 δ: proton ratio: 9:6:1 4 δ shifts

Key words & phrases: C7H16 Interpreting the C-13 NMR spectra of 3-ethylpentane, C-13 nmr spectrum of 3-ethylpentane, understanding the carbon-13 nmr spectrum of 3-ethylpentane, explaining the line pattern in the high resolution C-13 nmr spectra of 3-ethylpentane, revising the C-13 nmr spectrum of 3-ethylpentane, ppm chemical shifts of the C-13 nmr spectrum of 3-ethylpentane, how to construct the diagram of the C-13 nmr spectrum of 3-ethylpentane, how to analyse the chemical shifts in the carbon-13 NMR spectrum of 3-ethylpentane deducing the chemical environment of all the carbon atoms in 3-ethylpentane examining the c13 nmr spectrum of  3-ethylpentane analysing the 13-c nmr spectrum of 3-ethylpentane how do you sketch and interpret the C-13 NMR spectrum of 3-ethylpentane interpreting interpretation of the C-13 NMR spectrum of 3-ethylpentane 13C NMR spectrum of 3-ethylpentane (CH3CH2)3CH CH3CH2CH(CH2CH3)CH2CH3

Molecular structure diagram of the carbon-13 NMR diagram for the 13C NMR spectrum of 3-ethylpentane. Deducing the number of different chemical environments of the carbon atoms in the 3-ethylpentane molecule from the 13C chemical shifts in the carbon-13 NMR spectrum of 3-ethylpentane. Revision notes on the carbon-13 NMR spectrum of 3-ethylpentane. Matching and deducing the structure of the 3-ethylpentane molecule from its 13C NMR spectrum. Carbon-13 NMR spectroscopy of aliphatic alkanes, 13C NMR spectra of 3-ethylpentane, a structural isomer of molecular formula C7H16


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