Advanced Organic Chemistry: H-1 NMR spectrum of butan-1-olSITEMAP * HOME PAGE * SEARCH * GCSE Level Chemistry age ~14-16 * Advanced Level Chemistry age ~16-19
Interpreting the H-1 hydrogen-1 (proton) NMR spectrum of butan-1-ol
(1-butanol, prim-butyl alcohol, n-butyl alcohol) CH3CH2CH2CH2OH
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
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Chemical shift 2.24 ppm OH proton
Chemical shift 2.24 ppm 3rd CH2 protons
Note the increase in chemical shift as the alkyl protons are closer to the electronegative oxygen of the OH group.
Extra 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.
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.
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.
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