Interpretation of 1H NMR

Every organic compound produces a unique spectrum when analyzed by 1H NMR. The NMR spectrum (shown below) is made up of individual resonances (indicated with arrows). Every unique proton within a compound produces an individual resonance in the 1H NMR spectrum.

&'"(" !" #" $" %"

In both 13C NMR and 1H NMR, the chemical shift of each resonance (shown on the X-axis) is determined by the environment of the atom that produces it. Unlike in 13C NMR, the resonances in 1H NMR appear in complex splitting patterns due to the interactions of neighboring protons. Also, in 1H NMR, the integration of each resonance is proportional to the number of equivalent protons that produced the resonance. Questions: 1.! An organic compound is shown at the right. How many 1H NMR spectra does this compound have? 2.! How many 1H NMR resonances does this compound produce?

O
3.! The 1H NMR spectrum of this compound is shown above. Suppose you integrate resonances A and B. What do you expect the integration of each resonance to be? 4.! When you integrate the resonances, you find that the integration of each resonance is 4.5. How is this possible?

5.! If the integration of resonance A is 4.5, what should the combined integration of the E, F resonances be?

6.! Label the unique hydrogen below and assign the NMR spectrum using the letters provided.

Interpretation of 1H NMR
A similar molecule is shown below:

O Cl

CD3 CD3

Compared to the previous structure, this molecule has two features that complicate the interpretation of its 1H NMR spectrum. Identify these feature below: 1.

2.

Label the unique hydrogen atoms on this structure:

O Cl

CD3 CD3

Predict the 1H NMR spectrum. For each resonance, be sure to consider the splitting, chemical shift, and peak integration.

!"##########################################################################################################$#######################################################################################################"#