I\'m not sure about the second question Draw the expected structure of bupropion

Question

I'm not sure about the second question Draw the expected structure of bupropion hydrochloride dissolved in D_2O in the product box above. nothing changes (i.e. no reaction occurs with D_2O), then write "no reaction" in the box. We were able to record the H-NMR in D_2O and not our more typical solvent, CDCI_3. Which one of the following statements best explains why we couldn't use CDCI_3 as the solvent to obtain our NMR spectrum? i. Because the hydrochloride salt is the ionic form of bupropion, which we would expect to NOT be soluble in an organic solvent like CDCI_3. II. Because CDCI_3 would add a CI atom to the alpha-carbon, replacing the amine group. iii. Because CDCI_3 is less dense than D_2O.

Explanation / Answer

The correct choice for the second question will be (i).

The compound is a salt and we know that salts are usually very polar and ionic so it will dissolve in water(D2O) which is a strong polar solvent. CDCl3 being an organic solvent will not be able to dissolve the ionic compound and we know that the prerequisite for choosing NMR solvent is that, the compound must be soluble in the solvent. Hence , we cannot use CDCl3.

Now, as far as the addition of Cl to alpha-carbon is concerned, this is very unlikely. CDCl3 is a stable solvent and in the absence of any base or a catalyst, no reaction of CDCl3 with any compound will take place.

Lastly, we know that CHCl3 has higher density than H2O, so the third statement is a wrong statement.

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