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Advanced Organic Chemistry: Infrared spectrum of 1-chloro-2-methylpropane

Interpreting the infrared spectrum of 1-chloro-2-methylpropane

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 1-chloro-2-methylpropane

See also Comparing infrared, mass, 1H NMR & 13C NMR spectra of the 4 structural isomers of C4H9Cl

C4H9Cl (CH3)2CH2Cl infrared spectrum of 1-chloro-2-methylpropane wavenumbers cm-1 functional group detection fingerprint pattern identification of  isobutyl chloride doc brown's advanced organic chemistry revision notes 

Spectra obtained from a liquid film of 1-chloro-2-methylpropane. The right-hand part of the of the infrared spectrum of 1-chloro-2-methylpropane, wavenumbers ~1500 to 400 cm-1 is considered the fingerprint region for the identification of 1-chloro-2-methylpropane and most organic compounds. It is due to a unique set of complex overlapping vibrations of the atoms of the molecule of 1-chloro-2-methylpropane.

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For more see Molecular structure, classification and naming of halogenoalkanes (haloalkanes)

Interpretation of the infrared spectrum of 1-chloro-2-methylpropane

The most prominent infrared absorption lines of 1-chloro-2-methylpropane

For 1-chloro-2-methylpropane you observe C-H stretching vibrations at wavenumbers ~2880 to 3080 cm-1,

and C-H bending vibrations at wavenumbers ~1300 to 1500 cm-1.

These are typical infrared absorptions of molecules like 1-chloro-2-methylpropane with alkyl structures in them.

C-C-C skeletal vibrations from the CH3-C-CH3 grouping occur at wavenumbers ~1140 to 1175 cm-1. and 840 to 790 cm-1.

Characteristic groups of C-Cl vibration absorptions at wavenumbers ~580 to 780 cm-1 that you expect in halogenoalkane molecules like 1-chloro-2-methylpropane.

The absence of other specific functional group bands will show that a particular functional group is absent from the 1-chloro-2-methylpropane molecular structure.

Comparing the infrared, mass, 1H NMR and 13C NMR spectra of the 4 halogenoalkane isomers of C4H9Cl

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 1-chlorobutane, 2-chlorobutane, 1-chloro-2-methylpropane and 2-chloro-2-methylpropane image sizes.  These four molecules are structural isomers of molecular formula C4H9Cl and exemplify the infrared, mass, 1H NMR and 13C NMR spectra of lower aliphatic halogenoalkanes (haloalkanes, alkyl halides, chloroalkanes, alkyl chlorides).

INFRARED SPECTRA (above): Apart from the significant differences in the fingerprint region at wavenumbers 1500 to 400 cm-1, there are no other great striking differences, but each could be identified from its infrared spectrum. The infrared spectrum of 2-chloro-2-methylpropane is noticeably simpler in the fingerprint region, perhaps due to the greater symmetry of the molecule.

MASS SPECTRA (above): Theoretically, all four can give the parent molecular ions of m/z 92 and 94, but they are all relatively tiny peaks. 2-chlorobutane and 2-chloro-2-methylpropane give a base ion peak of m/z 57. The base ion peak for 1-chlorobutane is m/z 56 and that of 1-chloro-2-methylpropane is m/z 43. Each gives different patterns of pairs of m/z values two mass units apart, in the peak height ratio of 3:1, if the positive fragment contains a chlorine atom (35Cl or 37Cl) e.g look for m/z pairs 49/51, 63/65 and 77/79 in their mass spectra.

1H NMR SPECTRA (above): The 1H NMR spectra of all four molecules give different integrated proton ratios i.e.1-chlorobutane four peaks of ratio 3:2:2:2; 2-chlorobutane four peaks of ratio 3:3:2:1, 1-chloro-2-methylpropane three peaks of ratio 6:2:1 and 2-chloro-2-methylpropane gives just one peak '1' (effectively no ratio involved), so all four molecular structures can be distinguished from each other by their 1H NMR spectra proton ratios, numbers of peaks and (n+1) rule splitting patterns.

13C NMR SPECTRA (above): The 13C NMR spectra of the four molecules show various numbers of carbon-13 chemical environments i.e 1-chlorobutane and 2-chlorobutane show four 13C NMR resonances, 1-chloro-2-methylpropane three 13C NMR resonances and 2-chloro-2-methylpropane only two 13C resonances (3 and 2 chemical environments respectively. Therefore 1-chloro-2-methylpropane and 2-chloro-2-methylpropane can be distinguished from the other three by their number of resonances in their 13C NMR spectra, but 1-chlorobutane and 2-chlorobutane cannot be distinguished from each other from their number of 13C NMR resonance lines - other data would be required.

Key words & phrases: C4H9Cl (CH3)2CH2Cl image and diagram explaining the infrared spectrum of 1-chloro-2-methylpropane, complete infrared absorption spectrum of 1-chloro-2-methylpropane, comparative spectra of 1-chloro-2-methylpropane, prominent peaks/troughs for identifying functional groups in the infrared spectrum of 1-chloro-2-methylpropane, important wavenumber values in cm-1 for peaks/troughs in the infrared spectrum of 1-chloro-2-methylpropane, revision of infrared spectroscopy of 1-chloro-2-methylpropane, fingerprint region analysis of 1-chloro-2-methylpropane, how to identify 1-chloro-2-methylpropane from its infrared spectrum, identifying organic compounds like 1-chloro-2-methylpropane from their infrared spectrum, how to analyse the absorption bands in the infrared spectrum of 1-chloro-2-methylpropane detection of functional groups in the 1-chloro-2-methylpropane molecule example of the infrared spectrum of a molecule like 1-chloro-2-methylpropane with a functional group  interpreting interpretation of the infrared spectrum of 1-chloro-2-methylpropane shows presence of functional group  isobutyl chloride

Diagram of absorption of wavenumber peaks in the infrared spectrum of 1-chloro-2-methylpropane. Characteristic peak wavenumbers in the infrared spectrum of 1-chloro-2-methylpropane. Finger print identification pattern using the infrared spectrum of 1-chloro-2-methylpropane. Revision notes on the infrared spectrum of 1-chloro-2-methylpropane. Matching and deducing the structure of the 1-chloro-2-methylpropane molecule from  its infrared spectrum. Infrared spectroscopy of aliphatic halogenoalkanes haloalkanes alkyl halides alkyl chlorides chloroalkanes, infrared spectra of 1-chloro-2-methylpropane, an isomer of molecular formula C4H9Cl


Links associated with 1-chloro-2-methylpropane

The chemistry of HALOGENOALKANES (haloalkanes) revision notes INDEX

The mass spectrum of 1-chloro-2-methylpropane (isobutyl chloride)

The H-1 NMR spectrum of 1-chloro-2-methylpropane (isobutyl chloride)

The C-13 NMR spectrum of 1-chloro-2-methylpropane (isobutyl chloride)

Infrared spectroscopy index

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