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Advanced Organic Chemistry: H-1 NMR spectrum of 1-chlorobutane

The H-1 hydrogen-1 (proton) NMR spectrum of 1-chlorobutane

low and high resolution H-1 proton nmr spectrum of 1-chlorobutane analysis interpretation of chemical shifts ppm spin spin line splitting diagram n-butyl chloride doc brown's advanced organic chemistry revision notes

TMS is the acronym for tetramethylsilane, formula Si(CH3)4, whose protons are arbitrarily given a chemical shift of 0.0 ppm. This is the 'standard' in 1H NMR spectroscopy and all other proton shifts, called chemical shifts, depend on the individual (electronic) chemical environment of the hydrogen atoms in an organic molecule, 1-chlorobutane here.

The chemical shifts quoted in ppm on the diagram of the H-1 NMR spectrum of 1-chlorobutane represent the peaks of the intensity of the chemical shifts (which are often groups of split lines at high resolution) AND the relative integrated areas under the peaks gives you the ratio of protons in the different chemical environments of the 1-chlorobutane molecule.

 1-chlorobutane C4H9Cl, (c) doc b , (c) doc b

Interpreting the H-1 NMR spectrum of 1-chlorobutane

For relatively simple molecules, the low resolution H-1 NMR spectrum of 1-chlorobutane is a good starting point - just blur the above 4 sets of chemical shift lines above - which clearly show that there 4 sets of protons in different chemical environments.

You can illustrate this with a coloured structural formula of 1-chlorobutane.

CH3CH2CH2CH2Cl  (this is the nearest I get to an art installation!)

(note the 4 colours indicating the 4 different chemical environment of the hydrogen atoms).

The proton ratio is 3 : 2 : 2 : 2 for the four different proton environments giving four principal and different chemical shift peaks.

As you can see, the high resolution spectrum of 1-chlorobutane is complex

The left-hand end CH3 is split by the adjacent CH2 into a 1 : 2 : 1 triplet at 0.92 ppm.

The right-hand end CH2 is split into a 1 : 2 : 1 triplet by the adjacent CH2 at 3.42.

All three sets of CH2 protons are split on both sides by adjacent non-equivalent protons into multiple resonance lines.

CH3CH2CH2CH2Cl

The 1.41 ppm chemical shift:

From the n+1 rule, the 'left-hand' CH2 protons (H2) are split by CH3 protons (H3) and by the middle CH2 protons (H2), (5 protons in total), into a 1:5:10:10:5:1 sextet of resonance lines.

This is pattern of resonances is a good indication of a propyl group (CH3CH2CH2).

The 1.68 ppm chemical shift:

The middle CH2 protons (H2) are split on both sides by CH2 protons (H2 and H2), (4 protons in total), into a 1:4:6:4:1 quintet of resonance lines.

Neither of these is clear on the on the H-1 NMR spectra of 1-chlorobutane shown above.


Number of protons 1H causing splitting Splitting pattern produced from the n+1 rule and the theoretical ratio of line intensities
0 means no splitting             1            
1 creates a doublet           1   1          
2 creates a triplet         1   2   1        
3 creates a quartet       1   3   3   1      
4 creates a quintet     1   4   6   4   1    
5 creates a sextet   1   5   10   10   5   1  
6 creates a septet 1   6   15   20   15   6   1

Key words & phrases: Interpreting the proton H-1 NMR spectra of 1-chlorobutane, low resolution & high resolution proton nmr spectra of 1-chlorobutane, H-1 nmr spectrum of 1-chlorobutane, understanding the hydrogen-1 nmr spectrum of 1-chlorobutane, explaining the line splitting patterns in the high resolution H-1 nmr spectra of 1-chlorobutane, revising the H-1 nmr spectrum of 1-chlorobutane, proton nmr of 1-chlorobutane, ppm chemical shifts of the H-1 nmr spectrum of 1-chlorobutane, explaining and analyzing spin spin line splitting in the H-1 nmr spectrum, how to construct the diagram of the H-1 nmr spectrum of 1-chlorobutane, how to work out the number of chemically different protons in the structure of the 1-chlorobutane organic molecule, how to analyse the chemical shifts in the hydrogen-1 H-1 proton NMR spectrum of 1-chlorobutane


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