Advanced Organic Chemistry: 1H NMR spectrum of 2-iodo-2-methylpropane (CH3)3CI

HOME PAGE * SEARCH * GCSE Level Chemistry age ~14-16 * Advanced Level Chemistry age ~16-19

Interpreting and explaining the H-1 hydrogen-1 (proton) NMR spectrum of 2-iodo-2-methylpropane (tert-butyl iodide)

[Author © Dr Phil Brown PhD: Doc Brown's advanced level organic chemistry exam revision notes suitable for students of UK A level chemistry courses & US K12 grade 11, grade 12 and AP honors chemistry courses: Molecular spectroscopy analysis of 2-iodo-2-methylpropane (1H NMR spectra) [spectra page updated April 1st 2026 *]

 email doc brown Re-edit  1H NMR spectrum of (CH3)3CI

 Links associated with 2-iodo-2-methylpropane

 This is a BIG chemistry website, PLEASE take time to explore it

 H-1 proton NMR spectroscopy - spectra index  *  [privacy policy, cookies and disclaimer]

See also comparison of the infrared, mass, 1H NMR and 13C NMR spectra of the four isomers of C4H9I

Introductory note on the 1H NMR spectra of 2-iodo-2-methylpropane

Students and teachers please note my explanation of the proton NMR spectrum of 2-iodo-2-methylpropane is designed for advanced, but pre-university, chemistry courses.

The chemical shift δ splitting pattern effects for 2-iodo-2-methylpropane are confined to a proton spin-spin coupling effects analysed using the n+1 rule for adjacent non-equivalent proton fields (n is the number of neighbouring protons in a non-equivalent different chemical environment for the 2-iodo-2-methylpropane molecule).

It is assumed that the integrated intensities of the δ chemical shifts give the ratio of the protons in the different non-equivalent chemical environments of the 2-iodo-2-methylpropane molecule.

The most common solvent used for investigating the 1H NMR spectrum of compounds like 2-iodo-2-methylpropane, is CDCl3 and other deuterated solvents to avoid confusion with a 1H NMR signal, 2D (2H) has a different chemical shift.

1H proton nmr spectrum of 2-iodo-2-methylpropane low/high resolution diagrams (CH3)3CI analysis interpretation of chemical shifts ppm spin spin line splitting diagram H1 H-1 nmr for tert-butyl iodide explaining spin-spin coupling for line splitting 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 resonances, called chemical shifts, are measured with respect to the TMS, and depend on the individual (electronic) chemical environment of the hydrogen atoms in an organic molecule - 2-iodo-2-methylpropane here.

The chemical shifts quoted in ppm on the diagram of the H-1 NMR spectrum of 2-iodo-2-methylpropane 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 2-iodo-2-methylpropane molecule.

2-iodo-2-methylpropane (tert-butyl iodide), C4H9I, (CH3)3C-I

The molecular structure and naming of haloalkanes

Interpreting the H-1 NMR spectrum of 2-iodo-2-methylpropane

In terms of spin-spin coupling from the possible proton magnetic orientations, for 2-iodo-2-methylpropane I have only considered the interactions of non-equivalent protons on adjacent carbon atoms e.g. -CH2-CH3, -CH2-CH2- protons, but non of this applies to 2-iodo-2-methylpropane.

(CH3)3C-I

The 1H NMR spectrum

Chemical shifts (a)  on the H-1 NMR spectrum diagram for 2-iodo-2-methylpropane.

All nine protons are equivalent to each other due to the symmetry of the 2-iodo-2-methylpropane molecule with its three methyl groups attached to the same central carbon atom.

All you see is a single singlet 1H proton resonance line, chemical shift δ of 1.95 ppm.

Evidence of no non-equivalent C-H protons adjacent to each other, because no splitting is observed,

Although there are 9 hydrogen atoms in the molecule, the proton NMR spectrum shows there is only one possible chemical environment for all 9 hydrogen atoms in 2-iodo-2-methylpropane molecule.

Comparing the infrared, mass, 1H NMR and 13C NMR spectra of the 4 halogenoalkane isomers of C4H9I

NOTE: The images are linked to their original detailed spectral analysis pages AND can be doubled in size with touch screens to increase the definition to the original 1-iodobutane, 2-iodobutane, 1-iodo-2-methylpropane and 2-iodo-2-methylpropane image sizes.  These four molecules are structural isomers of molecular formula C4H9I and exemplify the infrared, mass, 1H NMR and 13C NMR spectra of lower aliphatic halogenoalkanes (haloalkanes, alkyl halides, iodoalkanes, alkyl iodides).

INFRARED SPECTRA (above): Apart from the significant differences in the fingerprint region at wavenumbers 1500 to 400 cm-1, there are no other great striking differences, but each could be identified from its infrared spectrum.

MASS SPECTRA (above): All four give the parent molecular ion of m/z 184, but it is only a relatively tiny peak for 2-iodo-2-methylpropane. All four give the base ion peak of m/z 57. All four give prominent peaks for m/z ions 29 and 41 and all give a tiny peak from an ionised iodine atom at m/z 127. They look quite similar to me and lack a clear fingerprint fragmentation pattern.

1H NMR SPECTRA (above): The 1H NMR spectra of all three molecules give different proton ratios i.e.1-iodobutane four peaks 3:2:2:2, 2-iodobutane four peaks 3:3:2:1, 1-iodo-2-methylpropane three peaks 6:2:1 and 2-iodo-2-methylpropane one peak '1' (effectively no ratio involved), so all four molecular structures can be distinguished from each other by their 1H NMR spectra proton ratios, numbers of peaks and (n+1) rule splitting patterns.

13C NMR SPECTRA (above): The 13C NMR spectra of the four molecules show various numbers of carbon-13 chemical environments i.e 1-iodobutane and 2-iodobutane show four 13C NMR resonances, 1-iodo-2-methylpropane three 13C NMR resonances and 2-iodo-2-methylpropane only two 13C resonances. Therefore 1-iodo-2-methylpropane and 2-iodo-2-methylpropane can be distinguished from the other three by their number of resonances in their 13C NMR spectra, but 1-iodobutane and 2-iodobutane cannot be distinguished from each other from their number of 13C NMR resonance lines - other data would be required.

The splitting pattern from proton spin-spin coupling effects is analysed using the n+1 rule for adjacent non-equivalent proton fields (n is the number of neighbouring protons in a non-equivalent different chemical environment) and applied to the 1H NMR spectrum of 2-iodo-2-methylpropane.
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

Key words & phrases: isomer of molecular formula (CH3)3CI Interpreting the proton H-1 NMR spectra of 2-iodo-2-methylpropane, low resolution & high resolution proton nmr spectra of 2-iodo-2-methylpropane, H-1 nmr spectrum of 2-iodo-2-methylpropane, understanding the hydrogen-1 nmr spectrum of 2-iodo-2-methylpropane, explaining the line splitting patterns from spin-spin coupling  in the high resolution H-1 nmr spectra of 2-iodo-2-methylpropane, revising the H-1 nmr spectrum of 2-iodo-2-methylpropane, proton nmr of 2-iodo-2-methylpropane, ppm chemical shifts of the H-1 nmr spectrum of 2-iodo-2-methylpropane, explaining and analyzing spin spin line splitting in the H-1 nmr spectrum, how to construct the diagram of the 1H nmr spectrum of 2-iodo-2-methylpropane, how to work out the number of chemically different protons in the structure of the 2-iodo-2-methylpropane organic molecule, how to analyse the chemical shifts in the hydrogen-1 H-1 proton NMR spectrum of 2-iodo-2-methylpropane using the n+1 rule to explain the spin - spin coupling ine splitting in the proton nmr spectrum of 2-iodo-2-methylpropane deducing the nature of the protons from the chemical shifts ppm in the H-1 nmr spectrum of 2-iodo-2-methylpropane examining the 1H nmr spectrum of 2-iodo-2-methylpropane analysing the 1H nmr spectrum of 2-iodo-2-methylpropane how do you sketch and interpret the H-1 NMR spectrum of 2-iodo-2-methylpropane interpreting interpretation of the 1H proton spin-spin coupling causing line splitting in the NMR spectrum of 2-iodo-2-methylpropane  assignment of chemical shifts in the proton 1H NMR spectrum of 2-iodo-2-methylpropane formula explaining spin-spin coupling for line splitting for 2-iodo-2-methylpropane  alkyl iodide haloalkane halogenoalkane tert-butyl iodide functional group Molecular structure diagram of the proton NMR diagram for the 1H NMR spectrum of 2-iodo-2-methylpropane. The proton ratio in the 1H NMR spectrum of 2-iodo-2-methylpropane. Deducing the number of different chemical environments of the protons in the 2-iodo-2-methylpropane molecule from the 1H chemical shifts in the hydrogen-1 NMR spectrum of 2-iodo-2-methylpropane. Analysing the high resolution 1H NMR spectrum of 2-iodo-2-methylpropane. Analysing the low resolution 1H NMR spectrum of 2-iodo-2-methylpropane. You may need to know the relative molecular mass of 2-iodo-2-methylpropane to deduce the molecular formula from the proton ratio of the 1H NMR spectrum of 2-iodo-2-methylpropane. Revision notes on the proton NMR spectrum of 2-iodo-2-methylpropane. Matching and deducing the structure of the 2-iodo-2-methylpropane molecule from its hydrogen-1 NMR spectrum. Proton NMR spectroscopy of halogenoalkanes iodoalkanes, 1H NMR spectra of 2-iodo-2-methylpropane, an isomer of molecular formula C4H9I How do you interpret the H-1 NMR spectrum of 2-iodo-2-methylpropane How to interpret the H-1 NMR spectrum of 2-iodo-2-methylpropane Explanatory diagram of the chemical shifts of the 1H H-1 proton NMR spectrum of the 2-iodo-2-methylpropane molecule in terms of its molecular structure. Listing data of all the chemical shift peaks in ppm in the proton NMR spectrum of 2-iodo-2-methylpropane. How to explain the H-1 NMR spectrum of 2-iodo-2-methylpropane. The chemical shifts and  integrated values of the proton ratios in the 1-H NMR spectrum of the 2-iodo-2-methylpropane molecule. How to work out the molecular structure of the 2-iodo-2-methylpropane molecule from its proton NMR spectrum. The uses and distinctive features of the proton NMR spectrum of the 2-iodo-2-methylpropane molecule explained. What does the H-1 proton NMR spectrum chemical shifts tell us about the structure and properties of the 2-iodo-2-methylpropane molecule? explaining the spin-spin proton coupling effects in the 1H NMR spectrum of 2-iodo-2-methylpropane. interpretation diagram explaining the proton splitting pattern produced from the n+1 rule and the theoretical ratio of chemical shift δ and values of intensities for the proton NMR spectrum lines of 2-iodo-2-methylpropane

Links associated with 2-iodo-2-methylpropane

The chemistry of HALOGENOALKANES (haloalkanes) revision notes INDEX

The infrared spectrum of 2-iodo-2-methylpropane (tert-butyl iodide)

The mass spectrum of 2-iodo-2-methylpropane (tert-butyl iodide)

The C-13 NMR spectrum of 2-iodo-2-methylpropane (tert-butyl iodide)

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

Use My Google search site box

Email doc b: chem55555@hotmail.com

Website content © Dr Phil Brown 2000+. All copyrights reserved on revision notes, images, quizzes, worksheets etc. Copying of Doc Brown's pre-university advanced level chemistry website material is NOT permitted. Exam revision summaries & references to science course specifications are unofficial. These organic chemistry revision notes on spectroscopy (on the 1H NMR spectrum of 2-iodo-2-methylpropane) are suitable for use of pre-university students studying AQA advanced level chemistry, Edexcel advanced level chemistry, OCR advanced level chemistry, IB advanced level chemistry, WJEC (Eduqas) advanced level chemistry, CIE advanced level chemistry, CCEA advanced level chemistry, US grade 11-12 AP honors chemistry courses and they will also prove useful to 1st year undergraduate students of chemistry.

TOP OF PAGE