Advanced Organic Chemistry: H-1 NMR spectrum of propanamide

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H-1 hydrogen-1 (proton) NMR spectrum of propanamide (propionamide)

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 propanamide

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H-1 proton NMR spectroscopy - spectra index

low and high resolution H-1 proton nmr spectrum of propanamide analysis interpretation of chemical shifts ppm spin spin line splitting diagram propionamide H1 1-H nmr 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 - propanamide here.

The chemical shifts quoted in ppm on the diagram of the H-1 NMR spectrum of propanamide 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 propanamide molecule.

propanamide (propionamide), C3H7NO, (c) doc b, (c) doc b, (c) doc b

Interpreting the H-1 NMR spectrum of propanamide

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

The hydrogen atoms (protons) of propanamide occupy 3 different chemical environments so that the low resolution NMR spectra should show 3 peaks of different H-1 NMR chemical shifts (diagram above for propanamide).

CH3CH2CONH2

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

Although there are 7 hydrogen atoms in the molecule, there only 3 possible chemical environments for the hydrogen atoms in propanamide molecule.

The proton ratio 3:2:2 observed, corresponds with the structural formula of propanamide.

The high resolution spectrum of propanamide

So, using the chemical shifts and applying the n+1 rule to propanamide

At 1.15 ppm the methyl proton resonance is split into a 1:2:1 triplet by the CH2 protons.

Evidence for the presence of a CH2 group in the molecule of propanamide

At 2.24 ppm the CH2 proton resonance is split into a 1:3:3:1 quartet by the CH3 protons.

Evidence for the presence of a CH3 group in the molecule of propanamide.

At 6.20 ppm there is a broad 'singlet' resonance band from the protons of the amino group.

Is it broadened due to some hydrogen bonding effect?

It appears as a singlet resonance because there is no proton on the adjacent atom to cause a splitting effect.

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

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Links associated with propanamide

The chemistry of CARBOXYLIC ACIDS and DERIVATIVES revision notes INDEX

H-1 proton NMR spectroscopy index  (Please read 8 points at the top of the 1H NMR index page)

ALL SPECTROSCOPY INDEXES

All Advanced Organic Chemistry Notes

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