Problem 2. Closely examine the structures of morphine-related drugs in the table

Question

Problem 2. Closely examine the structures of morphine-related drugs in the table below. They are fairly similar, yet, may be discriminated by IR techniques. Consult IR absorption tables to assist you to answer the questions in the table below to distinguish each of these from the others: give specific functional groups whose presence or absence would assist you best. If a structure would be easy to distinguish from the others, note it as Unique; if it would be difficult to distinguish it from the others, note it as Not-unique ?? N-CH3 N-CH CH3 Morphine Oxycodone Heroin Hydromorphone Distinctive IR Absorption(s) that help distinguish it from others. Give group and estimate of freq., if you can. Indicate if ths molecule provides a unique IR spectrum, or, can it be confused with another molecule here - not unique?

Explanation / Answer

How to distinguish the IR spectra of the following compounds?

Morphine will give 2 peaks for 2 OH at 3500-3300 cm-1 and N-CH3 will give a peak at 3500-3100 cm-1.

Oxycodone will give 1 peak at 1715 cm-1 for ketone group, OCH3 will give around 1710 and one more OH will give between 3500-3300 cm-1

heroin will give 2 peak at 1735 cm-1 for OCOCH3 (ester) and no alcohol peak and no ketone peak here.

Hydromorphone – peaks at 3300-3500 range for 1 OH and one peak at 1715 cm-1 for ketone.

The three benzene rings will give same spectra but the functional groups present in them will change its over all spectra from each other.

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