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Advanced Organic Chemistry: 1H NMR spectrum of chlorobenzene

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

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 chlorobenzene

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H-1 proton NMR spectroscopy - spectra index

C6H5Cl low and high resolution 1H proton nmr spectrum of chlorobenzene analysis interpretation of chemical shifts ppm spin spin line splitting diagram H1 H-1 nmr for chlorobenzene 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 - chlorobenzene here.

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

chlorobenzene, C6H5Cl, (c) doc b 

Interpreting the H-1 NMR spectrum of chlorobenzene

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

Chemical shifts (a) to (c) on the H-1 NMR spectrum diagram for chlorobenzene.

(a) to (b) 1H Chemical shift 7.14 to 7.43 ppm

All three proton resonances are close together, but you need very high resolution to sort them out.

Theoretically for the 1H NMR resonance peaks

(a) is for the proton attached to carbon atom C4.

(b) is for the protons attached to carbon atoms C3 and C5.

(c) is for the protons attached to carbon atoms C2 and C6.

The integrated proton ratio would be (1) : (2) : (2)

The group of these spectral lines is typical of a benzene ring group of protons e.g. in the molecule of chlorobenzene.

Number of directly adjacent protons 1H causing splitting Splitting pattern produced from the n+1 rule on spin-spin coupling 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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