Q.39. - Organic Chemistry

Question

Question: AZT was the first drug approved to treat HIV, the virus that causes AIDS. Explain why the six-membered ring of AZT is aromatic.

Step-by-Step Solution

Answer

Answer

 

The lone pair of electrons on the nitrogen atom takes part in resonance and leads to the enol formation, making AZT aromatic.

Step 1: AZT

Azidothymidine(AZT) is familiar with another name Zidovudine(ZDV). It belongs to the category of drugs noted as nucleoside reverse transcriptase inhibitors(NRTIs). It can be consumed via the mouth or could be injected via the vein.

Step 2: Aromatic compounds

Aromatic compounds are unreactive and are employed as solvents for numerous non-polar compounds. There are several aromatic compounds, and some of them include phenol and aniline.

Step 3: Aromaticity of AZT

The lone electron pair on the nitrogen atom takes part in resonance and leads to the enol formation. The resonance structure of AZT can be given as:

Resonance structure of AZT

 

The structure of AZT is cyclic, planar, completely conjugated, and comprised of  $6\mathrm{\pi } \mathrm{i}.\mathrm{e}. \left(4\times 1+2\right)\mathrm{\pi }$ electrons. Hence, this compound is aromatic.