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The following proton NMR spectrum is of a compound of molecular formula C3H80.

  1. Propose a structure for this compound.
  2. Assign peaks to show which protons give rise to which signals in the spectrum.

Short Answer

Expert verified

a)

b)


a = δ 4.0 (septet, 1H)

b = δ 2.5 (broad singlet, 1H)

c = δ 1.2 (doublet, 6H)

Step by step solution

01

Explanation of part (a):

From the given NMR spectrum, it was observed that, the chemical shift value occurs at 4.0 which suggests presence of electronegative atom as electronegative atom increases the chemical shift value of an adjacent proton by making the electron density less available and making the environment around that proton deshielded. Further splitting pattern confirmed that the electronegative atom is oxygen and since broad singlet is observed at 2.5 chemical shift value, this indicates presence of hydroxyl group. Chemical shift value of 1.2 indicates presence of methyl group and from the splitting patterns it is confirmed that structure would be propan-2-ol.

Propan-2-ol

02

Step 2:  Explanation of part (b):

A give signal will split and that splitting arises from spin-spin coupling which means the interaction which takes place between neighboring and non-equivalent nuclei. A septet is observed for proton-a, as the proton-a is surrounded by two methyl groups which means 6 hydrogens will split the signal for this one proton into septet. A doublet pattern is observed for both methyl groups as there is only one proton which is present that is of methine carbon which can take part in splitting. A broad singlet is observed for hydroxyl proton, as hydroxyl proton is acidic and thus is rapidly exchangeable and there is no proton present nearby which split this hydroxyl proton, thus a singlet is observed.

a = δ 4.0 (septet, 1H)

b = δ 2.5 (broad singlet, 1H)

c = δ 1.2 (doublet, 6H)

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Most popular questions from this chapter

Draw the NMR spectra you expect for the following complexes.

A small pilot was adding bromine across the double bond of but-2-ene to make 2,3-dibromobutane. A controller malfunction allowed the reaction temperature to rise beyond safe limits. A careful distillation of the product showed that several impurities had formed, including the one having the NMR spectra that appear below. Determine its structure and assign the peaks to the protons in your structure.

A laboratory student was converting cyclohexanol to cyclohexyl bromide by using one equivalent of sodium bromide in a large excess of concentrated sulfuric acid. The major product she recovered was not cyclohexyl bromide, but a compound of formula C6H10that gave the following 13CNMR spectrum:

  1. Propose a structure for this product.
  2. Assign the peaks in the 13CNMR spectrum to the carbon atoms in the structure.
  3. Suggest modifications in the reaction to obtain a better yield of cyclohexyl bromide.

Question:In a 300-MHz spectrometer, the protons in bromomethane absorb at a position 660 Hz downfield from TMS.

(a) What is the chemical shift of these protons?

(b) What is the chemical shift of the bromomethane protons in a 60-MHz spectrometer?

(c) How many hertz downfield from TMS would they absorb at 60 MHz?

Determine the ratios of the peak areas in the following spectra. Then use this information, together with the chemical shifts, to pair up the compounds with their spectra. Assign the peaks in each spectrum to the protons they represent in the molecular structure.

Possible structures:

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