Question

The structure of `AZT` (azidothymine) is given below. It is used to treat `AIDS` patients. If fights and `AIDS` infection but does not cure it.

Which of the following statements are correct about `AZT` ?
A. It shows acidic property.
B. It undergoes tautomerisation.
C. It gives white precipitate with `(ZnCl_2 + HCl)` (Lucas reagent).
D. Azide ion `(N_3^(Ө))` cannot replace `Br^(Ө))` by `SN^2` reaction.

Answer 1

Correct Answer - A::B::D
For `(a), H` atom attached to `N` is acidic due to the presence of the two electron-withdrawing `(C=O)` groups. Its ion is resonance stabilised.

`( c) 1^@ ROH` does not give Lucas test at room temperature.
`(d)` Strong `(C-N)` bond is not broken by `Br^(Ө)`.