${\mathrm{C}}_3{\mathrm{H}}_9\mathrm{N}\underset{{\mathrm{KMnO}}_4}{\overset{\left(\mathrm{O}\right)}{\to }}$Mixture of A+B

Mixture of A+B$\underset{2.{\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{1.{\mathrm{CH}}_3\mathrm{MgBr}}{\to }}$Mixture of C+D

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Mixture of A+B can't be identified by tollen's reagent

Mixture of C+D can't be identified by lucas test

Mixture of C+D can be identified by iodoform test

Mixture of A+B can be identified by 2,4-DNP reagent