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Advanced Chemistry: Carbon-13 NMR spectrum of E-pent-2-ene, Z-pent-2-ene

The Carbon-13 NMR spectrum of E-pent-2-ene and Z-pent-2-ene

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 E-pent-2-ene and Z-pent-2-ene

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

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 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.

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).


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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

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

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