Question

Three organic compounds A, B and C are non cyclic functional isomers of carbonyl compounds with molecular formula C₄H₈O. Isomers A and C give positive Tollen’s test while compound B does not give positive Tollen’s test but gives positive iodoform test. Compounds A and B on reduction with Zn amalgam and conc. HCl give the same product.

1. Write the structures of the compounds A, B and C.
2. Out of the compounds A, B and C, which one will be the least reactive towards addition of HCN.

Answer 1

(a)  [A] = CH₃CH₂CH₂CHO

[B] = CH₃COCH₂CH₃

[C] = CH₃CH(CH₃)CHO

(b) [B] will be least reactive towards addition of HCN.