NMR Practice Practice Problems

Draw the ¹H NMR spectrum of the following molecule making sure to show the integration of each peak, without thinking about the relative placement of the signals (i.e., the chemical shift) or the splitting patterns. Label each signal according to the set of equivalent hydrogens to which it belongs.

For the following compound, draw an estimated ¹H NMR spectrum, and show the multiplicity, integration, and chemical shift of each signal. Mark the signals according to the sets of equivalent hydrogens.

For the given compound, draw an estimated ¹H NMR spectrum, and show the multiplicity, integration, and chemical shift of each signal. Mark the signals according to the sets of equivalent hydrogens.

Draw the expected ¹H NMR spectrum for the following molecule.

Match the peaks in the 1H NMR spectrum of the given molecule with their corresponding hydrogens.

Produce a table of chemical shifts, integrations, and multiplicities of each ¹H NMR peak expected from the labeled protons of the following compound.

Draw the expected 1H NMR spectrum for the molecule shown below.

From the given ¹H NMR spectra of the reactant and the product below. Draw a plausible mechanism for the reaction.

Draw the expected ¹H NMR spectrum for the following compound.

From the given ¹H NMR spectra below, draw the structure of the reactants and the product.

¹H NMR is frequently used to confirm that a reaction has proceeded as anticipated by comparing the spectrum of the product with what is anticipated. Draw the spectrum you would expect to see for the resulting product using the following ¹H NMR spectrum of the reactant.

What is the structure of the compound that has the following ¹H NMR spectrum data and molecular formula of C₅H₁₁Cl? 

1 H quintet at 3.38 ppm, 1 H octet at 1.91 ppm, 3 H doublet at 1.55 ppm, 6 H doublet at 0.88 ppm

Which compound produced the following ¹H NMR spectrum?

Describe the expected ¹H NMR spectrum and indicate the relative position of the signals for the given compound.

Describe the expected ¹H NMR spectrum and indicate the relative position of the signals for the given compound.

Describe the expected ¹H NMR spectrum and indicate the relative position of the signals for the given compound.

Determine the structure of the compound with the molecular formula C₁₄H₂₂O₂, which produces the following spectrum. (Note: The integral ratios are given across the spectrum from left to right.) 

A ¹H NMR spectrum containing two singlets with integral ratios of 2:9.

Differentiate two isomers (a primary alcohol and an ether) with the molecular formula C₃H₈O using ¹H NMR.

What are the chemically nonequivalent proton ratios in the compound if the integration curve steps from left to right across the spectrum are 61, 122, 61, and 366 mm? Which of the following compounds would exhibit this sequence of integrals in a ¹H NMR spectrum?

i.  ii.  

iii.  iv.

True or False. The ¹H NMR spectrum below corresponds to the given compound.

Which of the three isomers with the molecular formula C₆H₁₁Cl has the following ¹H NMR spectrum?

Which of the three isomers with the molecular formula C₅H₈Cl₂ has the following ¹H NMR spectrum?

Which of the three isomers with the molecular formula C₅H₁₀Cl₂ has the following ¹H NMR spectrum?

The ¹H NMR spectrum of the compound created by the reaction of an alkyl halide and an alkoxide ion is shown here. What are the structures of the alkyl halide and alkoxide ion?

Which of the three isomers with the molecular formula C₆H₁₂O has the following ¹H NMR spectrum?

What is the structure of the compound with a molecular formula of   C₄H₈O₂ that has the following ¹H NMR and IR spectra? 

What is the structure of the compound with a molecular formula of C  ₄H₈O₂ that has the following ¹H NMR and IR spectra?

Assign the protons responsible for each of the signals in the ¹H NMR spectrum for 2,4-dimethyl-3-pentanol.

Describe the ¹H NMR spectrum for an anhydrous sample of 3-chloro-3-methylbutan-1-ol.

Describe the ¹H NMR spectrum for a sample of 3-chloro-3-methylbutan-1-ol with a trace amount of acid.

The ¹H NMR spectrum below is produced by a compound with the molecular formula C₅H₁₀O₂. What is its structure?

What is the structure of the compound with a molecular formula of C ₉H₁₈O that has the following ¹H NMR and IR spectra?

The IR spectrum of compound A with the molecular formula C ₃H₆O is shown below.

It undergoes reduction to produce compound B whose ¹H NMR spectrum is displayed below. 

Determine the structure of the compounds.

Draw the most probable NMR spectra for the compound below:

Draw the possible NMR spectra for the compound below:

Using the proton NMR spectra specify the characteristic difference in peaks between the pair of compounds in each of the following. 

Predict the possible NMR spectra for the molecule below.  

Below are characteristic proton NMR signals for each of the four structures. Each has the molecular formula C₆H₁₂O₂. Match the correct proton NMR signals with their corresponding structure. 

(I) 3H triplet at 1.1 ppm and 2H quartet at 2.3 ppm 

(II) 6H doublet at 0.9 ppm and 3H singlet at 3.7 ppm 

(III) 6H doublet at 0.9 ppm and 1H broad singlet at 11.0 ppm 

(IV) 3H singlet at 2.3 ppm and 1H broad singlet at 3.6 ppm

Propose a structure of the compound with molecular formula C₅H₁₂O that gives the following NMR spectrum. Assign the molecule's protons, giving rise to labeled peaks in the spectrum. 

One Strong and another medium IR absorption at 1650 cm⁻¹ and 1700 cm⁻¹ were observed for an unknown compound with molecular formula C₃H₃BrO. The proton NMR spectrum of the compound shows two doublets at 6.7 ppm and 7.3 ppm, respectively, with J = 14 Hz and one singlet at 9.7 ppm. Predict the structure consistent with the above information.

Predict the possible NMR spectra for the molecule below.  

Determine the structure for the following NMR spectrum and molecular formula. Also, state the type of protons that give the peaks at 2.5 ppm and 2.7 ppm. 

Molecular Formula: C₆H₁₀O₃

Predict the spectral assignments for the protons in 3-methylbutan-2-ol along with the multiplicity and integration. Note: Integration refers to area or number of protons corresponding to a particular peak. 

A proton NMR spectrum along with the molecular formula is given below. Identify the structure that is consistent with the given NMR spectrum and molecular formula.

Proton NMR spectrum of an unknown compound with molecular formula C₁₃H₁₃BrO₆ has three singlets:

At 3.9 ppm for 9H 

At 4.6 ppm for 2H

At 8.1 ppm for 2H

Identify the most probable structure for this compound.

Using the proton NMR spectra specify the characteristic difference in peaks between the pair of compounds in each of the following. 

Identify the NMR spectrum for ethyl isobutyrate from the options below and identify the two main peaks that make it different from the spectrum of isopropyl propionate.  

An unknown compound with a molecular formula C₈H₈O₂ shows the following NMR spectra. Propose a structure consistent with the observed absorptions.

An unknown compound with a molecular formula C₄H₆O₂ shows the following NMR spectrum. Propose a structure consistent with the observed absorptions.