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Advanced Organic Chemistry: Infrared spectrum of cyclopropane

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Interpreting the infrared spectrum of cyclopropane

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 infrared spectra of cyclopropane

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Infrared spectroscopy - spectra index

See also comparing the infrared, mass, 1H NMR and 13C NMR spectra of propane, cyclopropane and propene

infrared spectrum of cyclopropane C3H6 wavenumbers cm-1 functional group detection fingerprint pattern identification of cyclopropane doc brown's advanced organic chemistry revision notes 

Spectra obtained from a liquid film of cyclopropane. The right-hand part of the of the infrared spectrum of cyclopropane, wavenumbers ~1500 to 400 cm-1 is considered the fingerprint region for the identification of cyclopropane and most organic compounds. It is due to a unique set of complex overlapping vibrations of the atoms of the molecule of cyclopropane.

Cyclopropane C3H6, alkanes structure and naming (c) doc b , alkanes structure and naming (c) doc b

Interpretation of the infrared spectrum of cyclopropane

The most prominent infrared absorption lines of cyclopropane

C-H stretching vibrations peak at wavenumbers ~3080 to 3040  cm-1 for cyclopropane.

Not sure what vibrations cause the sharp band at ~2200 cm-1.

-CH2- deformation vibrations peak at wavenumbers 1480 to 1440 cm-1 for cyclopropane.

Cyclopropane shows -CH2- skeletal vibration absorption bands peaking at wavenumbers 1020 to 1000 cm-1.

Cyclopropane shows many absorption bands in common with aliphatic hydrocarbon molecules.

The absence of other specific functional group bands will show that a particular functional group is absent from the cyclopropane molecular structure.

Comparing the infrared, mass, 1H NMR and 13C NMR spectra of propane, cyclopropane and propene

NOTE: The images are linked to their original detailed spectral analysis pages AND can be doubled in size with touch screens to increase the definition to the original ethane and ethene image sizes.

Comparing the infrared spectra of propane, propene and cyclopropane.

Cyclopropane and propene are structural isomers of molecular formula C3H6.

Propane and propene exemplify the infrared spectra of lower members of  the alkane and alkene homologous series of CnH2n+2 and CnH2n hydrocarbon molecules where n = 3.

INFRARED SPECTRA (above): Apart from the significant differences in the fingerprint region at wavenumbers 1500 to 400 cm-1, the most striking differences are: (i) propene shows the characteristic absorption at ~1700 cm-1 for the C=C stretching vibrations, absent in the other two spectra, (ii) cyclopropane shows an absorption band at 2200 cm-1, absent in the other two spectra, (iii) propane has an absorption band at ~750 cm-1, absent in the other two spectra.

Comparing the mass spectra of propane, propene and cyclopropane.

Cyclopropane and propene are structural isomers of molecular formula C3H6.

Propane and propene exemplify the mass spectra of lower members of  the alkane and alkene homologous series of CnH2n+2 and CnH2n hydrocarbon molecules where n = 3.

MASS SPECTRA (above): All three hydrocarbons show some similarities in their mass spectra e.g. m/z ions 26 to 28 for [C2Hx]+ (x = 2 to 4) and m/z 14 and 15 ions - but these are found in most aliphatic hydrocarbon spectra. The molecular ion peaks will be the same for the isomeric propene and cyclopropane (m/z 42) but that of propane will be 2 mass units higher at m/z 44. The base ion peak m/z values are all different, propane 29, propene 41 and cyclopropane 42.

Comparing the 1H proton NMR spectra of propane, propene and cyclopropane.

Cyclopropane and propene are structural isomers of molecular formula C3H6.

Propane and propene exemplify the 1H proton NMR spectra of lower members of  the alkane and alkene homologous series of CnH2n+2 and CnH2n hydrocarbon molecules where n = 3.

1H NMR SPECTRA (above): The 1H NMR spectra of all three molecules give different proton ratios i.e. propane 3:1 (actually 6:2 in the molecule), propene 2:1:3 (spectrum and molecule) and cyclopropane just a singlet for the six protons, so all three can be distinguished from each other by their 1H NMR spectra..

Comparing the carbon-13 NMR spectra of propane, propene and cyclopropane.

Cyclopropane and propene are structural isomers of molecular formula C3H6.

Propane and propene exemplify the carbon-13 NMR spectra of lower members of  the alkane and alkene homologous series of CnH2n+2 and CnH2n hydrocarbon molecules where n = 3.

13C NMR SPECTRA (above): The 13C NMR spectra of the three molecules show different numbers of carbon-13 chemical environments i.e propane 2, propene 3 and cyclopropane only 1, so all three could be distinguished from each other.

Key words & phrases: C3H6 image and diagram explaining the infrared spectrum of cyclopropane, complete infrared absorption spectrum of cyclopropane, comparative spectra of cyclopropane, prominent peaks/troughs for identifying functional groups in the infrared spectrum of cyclopropane, important wavenumber values in cm-1 for peaks/troughs in the infrared spectrum of cyclopropane, revision of infrared spectroscopy of cyclopropane, fingerprint region analysis of cyclopropane, how to identify cyclopropane from its infrared spectrum, identifying organic compounds like cyclopropane from their infrared spectrum, how to analyse the absorption bands in the infrared spectrum of cyclopropane detection of functional groups in the cyclopropane molecule example of the infrared spectrum of a molecule like cyclopropane with a ? functional group  interpreting interpretation of the infrared spectrum of cyclopropane shows presence of cycloalkane functional group Diagram of absorption of wavenumber peaks in the infrared spectrum of cyclopropane. Characteristic peak wavenumbers in the infrared spectrum of cyclopropane. Finger print identification pattern using the infrared spectrum of cyclopropane. Revision notes on the infrared spectrum of cyclopropane. Matching and deducing the structure of the cyclopropane molecule from  its infrared spectrum.

Links associated with cyclopropane

The chemistry of ALKANES revision notes INDEX

The mass spectrum of cyclopropane

The H-1 NMR of cyclopropane

The C-13 NMR spectrum of cyclopropane

Infrared spectroscopy index

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