Advanced Chemistry: 13C NMR spectrum of E-pent-2-ene and Z-pent-2-ene CH3CH=CHCH2CH3

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Interpreting the Carbon-13 NMR spectrum of E-pent-2-ene and Z-pent-2-ene (E/Z geometrical isomers)

[Author © Dr Phil Brown PhD: Doc Brown's advanced level organic chemistry exam revision notes suitable for students of UK A level chemistry courses & US K12 grade 11, grade 12 and AP honors chemistry courses: Molecular spectroscopy analysis of E/Z isomers of pent-2-ene [spectra page updated Mar 25th 2026 *]

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Introductory note on the 13C NMR spectrum of E/Z pent-2-ene (cis/trans isomers)

Students and teachers please note that my explanation of the carbon-13 NMR spectrum of E/Z pent-2-ene (cis/trans isomers) is designed for advanced, but pre-university, chemistry courses.

The description does not involve the chemical shift δ spin-spin coupling effects for E/Z pent-2-ene (cis/trans isomers) and the relative size of the carbon-13 NMR shifts does not give the ratio of the carbon atoms in the different non-equivalent chemical environments of the E/Z pent-2-ene (cis/trans isomers) molecule.

The most common solvent used for investigating the C13 NMR spectrum of compounds like E/Z pent-2-ene (cis/trans isomers), is CDCl3 and other deuterated solvents.

C5H10 C-13 nmr spectrum of E-pent-2-ene 2-pentene analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of trans-pent-2-ene C13 13-C nmr doc brown's advanced organic chemistry revision notes 

The C-13 NMR spectrum of the stereoisomer E-pent-2-ene (trans-2-pentene)

 

C5H10 C-13 nmr spectrum of 2-pentene Z-pent-2-ene analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of cis-pent-2-ene C13 13-C nmr doc brown's advanced organic chemistry revision notes

The C-13 NMR spectrum of the stereoisomer Z-pent-2-ene (cis-2-pentene)

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 - E-pent-2-ene and Z-pent-2-ene here.

Pent-2-ene C5H10, alkenes structure and naming (c) doc b has two E/Z isomers E-pent-2-ene and Z-pent-2-ene

Z/cis- alkenes structure and naming (c) doc b , E/trans- alkenes structure and naming (c) doc b

The molecular structure and naming of alkenes

Interpreting the C-13 NMR spectrum of E-pent-2-ene and Z-pent-2-ene

As you can see from the diagram above there are 5 different 13C chemical shift lines in the C-13 NMR spectrum of both E-pent-2-ene and Z-pent-2-ene indicating 5 different chemical environments of the carbon atoms.

Both carbon-13 NMR spectra are quite similar, the CH carbon atoms of the C=C double bond both have a larger 13C chemical shifts close together, whereas the other three carbon atoms of the linear carbon chain have similar and smaller shifts, also relatively close together.

Although not identical spectra, both pent-2-ene E/Z isomers show a very similar pattern of 13C NMR chemical shifts.

CH3CH=CHCH2CH3

(Note the 5 colours indicating the 5 different chemical environments of the carbon atoms in E-pent-2-ene and Z-pent-2-ene).

The carbon-13 NMR spectra a provides direct evidence of 5 different carbon atom environments in both E-pent-2-ene and Z-pent-2-ene molecule from 5 different chemical shifts (ppm) (a) to (e).

The 13C NMR chemical shifts tend to much higher for the unsaturated carbon atoms of the C=C double bond compared to those not so.

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Links associated with E-pent-2-ene and Z-pent-2-ene

The chemistry of ALKENES revision notes INDEX

C-13 NMR spectroscopy index

The infrared spectra of the E/Z isomers of pent-2-ene (cis/trans isomers of 2-pentene)

The mass spectra of the E/Z isomers of pent-2-ene (cis/trans isomers of 2-pentene)

The H-1 NMR spectra of the E/Z isomers of pent-2-ene (cis/trans isomers of 2-pentene)

ALL SPECTROSCOPY INDEXES

STEREOISOMERISM general definition, E/Z (geometric/geometrical cis/trans) isomerism

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