Question

a. Distinguish between `1^(@),2^(@)`, and `3^(@)` amines by using succine anhydride `(A)`.
b. What are the limitations of Hinsberg reagent?
c. Give the structural formula of a chiral compound `C_(8)H_(11)N(X)`, which dissolves in dilute `HCl` and evolves `N_(2)` gas with `HNO_(2)`.

Answer 1

(iii) `3^(@)` amine does not react with `(A)`, the unreacted amine dissolve in aqueous acid `(H_(3)O^(o+))`.
b. The amines must be water-insoluble liquids.
c. `D.U.` in `(X)=((2n_(C)+2)-(n_(H)-n_(N)))/(2)=(18-10)/(2)=4^(@)`
(i) `4 D.U.` in `(X)` suggests that it contains benzene ring.
(ii) `(X)` is a `1^(@)` amine since it dissolve in `HCl` and gives `N_(2)` with `HNO_(2)`.
(iii) The remaning `C` atom the `NH_(2)` must form a chiral molecule. So, `(X)` is :