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Advanced Organic Chemistry: H-1 NMR spectrum of butan-1-ol

The H-1 hydrogen-1 (proton) NMR spectrum of butan-1-ol (1-butanol)

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 H-1 NMR spectra of butan-1-ol 1-butanol

low resolution H-1 proton nmr spectrum of butan-1-ol analysis interpretation of chemical shifts ppm spin spin line splitting diagram H1 1-H nmr for 1-butanol 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 - butan-1-ol here.

The chemical shifts quoted in ppm on the diagram of the H-1 NMR spectrum of butan-1-ol represent the peaks of the intensity of the chemical shifts of (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 butan-1-ol molecule i.e. 3 : 2 : 2 : 2 :1.

Butan-1-ol C4H10O , alcohols and ether structure and naming (c) doc b . alcohols and ether structure and naming (c) doc b

Interpreting the H-1 NMR spectrum of butan-1-ol (1-butanol, n-butyl alcohol)

For relatively simple molecules, the low resolution H-1 NMR spectrum of butan-1-ol is a good starting point.

The hydrogen atoms (protons) of butan-1-ol occupy 5 different chemical environments so that the low resolution NMR spectra should show 5 peaks of different H-1 NMR chemical shifts (diagram above for butan-1-ol).

CH3CH2CH2CH2OH

Note the ratio 3:2:2:2:1 of the 5 colours of the protons in the 5 chemically different environments

Although there are 10 hydrogen atoms in the molecule, there only 5 possible chemical environments for the hydrogen atoms in butan-1-ol molecule.

The proton ratio 3:2:2:2:1 observed, corresponds with the structural formula of butan-1-ol.

The high resolution spectrum of butan-1-ol

high resolution H-1 proton nmr spectrum of butan-1-ol analysis interpretation of chemical shifts ppm spin spin line splitting diagram H1 1-H nmr for 1-butanol doc brown's advanced organic chemistry revision notes

The low and high resolution spectra of butanal show 5 groups of protons and in the ratio expected from the formula of butan-1-ol, namely 3:2:2:2:1, but the high resolution spectrum is very complex.

The ppm quoted on the diagram represent the peak of resonance intensity for a particular proton group in the molecule of butan-1-ol - since the peak' is at the apex of a band of H-1 NMR resonances due to spin - spin filed splitting effects - see high resolution notes on butan-1-ol below.

CH3CH2CH2CH2OH (below I will refer to the 1st, 2nd and 3rd CH2 groups from left to right)

So, using the chemical shifts and applying the n+1 rule to butan-1-ol

Chemical shift 0.94 ppm CH3 protons

The end methyl group proton resonance is split into a 1:2:1 triplet by the first CH2 group (2 protons, n+1 = 3 = triplet).

Evidence for the presence of a CH2 group in the molecule of butan-1-ol.

Chemical shift 1.39 ppm 1st CH2 protons

The first CH2 proton resonance is split by the CH3 protons AND the 2nd CH2 protons into a 1:5:10:10:5:1 sextet (5 protons, n+1 = 6 = sextet).

Evidence for the presence of a CH3CH2CH2 group in the molecule of butan-1-ol

Chemical shift 1.53 ppm 2nd CH2 protons

The 2nd CH2 proton resonance is split on either side by the 1st and 3rd CH2 protons into a 1:4:6:4:1 quintet (4 protons, n+1 =5 = quintet).

Evidence for the presence of a CH2CH2CH2 group in the molecule of butan-1-ol.

Chemical shift 2.24 ppm OH proton

The OH proton resonance is often seen and 'portrayed' as a singlet.

Normally the O-H proton resonance is not split by adjacent carbon atom protons and neither does it, in turn, split the resonance of the same adjacent protons (see extra note below).

Chemical shift 2.24 ppm 3rd CH2 protons

You can consider that the 3rd CH2 proton resonance is split by the 2nd CH2 protons into a 1:2:1 triplet (2 protons, n+1 = 3 = triplet, as on diagram).

Note that no splitting due to OH proton is detected.

 

Note on the OH proton resonance

If the alcohol is impure, containing water or any source of labile protons, because water and the alcohol exchange protons e.g.

R-O-H  +  H-O-H    R-O-H  +  H-O-H

This means the CH2 protons no longer experience a 'simple' local field from one singlet proton from two possible orientations, but, over a finite period, experience the averaging effect of exchanging protons.

This removes the spin - spin coupling effect and the OH proton resonance just shows up as a singlet if the butan-1-ol contains even a trace of water (or acid).

This sort of exchange cannot happen with the alkyl protons, but is common with molecules containing a hydroxylic (OH) hydrogen atom like alcohols and carboxylic acids.

Not only that, you also get proton transfer between the alcohol molecules i.e.

R-O-H  +  H-O-R    R-O-H  +  H-O-R

which gives the same effect as traces of water of acid.

So, in butan-1-ol, all you usually see in the H-1 NMR spectrum is the mutual splitting of the CH2 and CH3 proton resonances plus a singlet line for the OH proton resonance.

 


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: 1-butanol n-butyl alcohol Interpreting the proton H-1 NMR spectra of butan-1-ol, low resolution & high resolution proton nmr spectra of butan-1-ol, H-1 nmr spectrum of butan-1-ol, understanding the hydrogen-1 nmr spectrum of butan-1-ol, explaining the line splitting patterns in the high resolution H-1 nmr spectra of butan-1-ol, revising the H-1 nmr spectrum of butan-1-ol, proton nmr of butan-1-ol, ppm chemical shifts of the H-1 nmr spectrum of butan-1-ol, 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 butan-1-ol, how to work out the number of chemically different protons in the structure of the butan-1-ol organic molecule, how to analyse the chemical shifts in the hydrogen-1 H-1 proton NMR spectrum of butan-1-ol using the n+1 rule to explain the spin - spin coupling ine splitting in the proton nmr spectrum of butan-1-ol deducing the nature of the protons from the chemical shifts ppm in the H-1 nmr spectrum of butan-1-ol examining the 1H nmr spectrum of  butan-1-ol analysing the 1-H nmr spectrum of butan-1-ol how do you sketch and interpret the H-1 NMR spectrum of butan-1-ol 1-butanol n-butyl alcohol


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