Compound A (molecular formula `C_(3)H_(8)O` ) is treated with acidified potassium dichromate to form a product B (molecular formula `C_(3)H_(6)O`) . B forms a shining silver mirror on warming with ammonical silver nitrate , B when treated with an aqueous solution of `NH_(2)NHCONH_(2)` and sodium acetate gives a product C . identify the structure of C .

Options

A. `CH_(3)CH_(2)CH=N NHCONH_2`
B. `CH_(3)-underset(CH_(3))underset(|)(C)=N NHCONH_(2)`
C. `CH_(3)-underset(CH_(3))underset(|)(C)=N CONHNH_(2)`
D. `CH_(3)CH_(2)CH=NCONHNH_(2)`

Answer

A

Explanation

Since (B), M.F. `C_(3)H_(6)O` forms a shining silver mirror on warming with ammonical `AgNO_(3)` (Tollens' reagent), (B) must be an aldehyde, i.e., `CH_(3)CH_(2)CHO and 'A'` with M.F. `C_(3)H_(8)O` must be a `1^(@)` alcohol, i.e., `CH_(3)CH_(2)CH_(2)OH`. during the reaction of 'B' with `H_(2)NCONHNH_(2)`. HCl, the more nucleophilic `NH_(2)` i.e., `NH_(2)` next to NH reacts giving product (C), i.e., option (a) is correct.
`underset("1-Propanol (A) "(M.F.C_(3)H_(8)O))(CH_(3)CH_(2)CH_(2)OH) underset(H_(2)SO_(4))overset(K_(2)Cr_(2)O_(7))to underset("Propanal (B) "(M.F.C_(3)H_(6)O))(CH_(3)CH_(2)CHO) underset("Sod. acetate "(-HCl,-H_(2)O))overset(H_(2)NCONHNH_(2).HCl)to CH_(3)CH_(2)CH=N NHCONH_(2)`.