Compound 'A' (molecular Formula C3H8O ) Is Treated With Acidified ...

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4. Compound 'A' (molecular formula C3H8O ) is treated with acidified potassium dichromate to form a product 'B' (molecular formula C3H6O) 'B' forms a shining silver mirror on warming with ammoniacal silver nitrate. 'B' when treated with an aqueous solution of H2NCONHNH2 and sodium acetate gives a product -C Identify the structure of 'C'.

Q. Compound 'A' (molecular formula C3​H8​O ) is treated with acidified potassium dichromate to form a product 'B' (molecular formula C3​H6​O) 'B' forms a shining silver mirror on warming with ammoniacal silver nitrate. 'B' when treated with an aqueous solution of H2​NCONHNH2​ and sodium acetate gives a product -C Identify the structure of 'C'. 7490 272 IIT JEEIIT JEE 2002Alcohols Phenols and Ethers Report Error A

CH3​CH2​CH=NNHCONH2​

36% B 22% C 31% D

CH3​CH2​OH+NCONHNH2​

11%

Solution:

A is an alcohol and its oxidation product gives Tollen's test, i.e. B must be an aldehyde (CH3​CH2​CHO). CH3​CH2​CHO+semicarbazideH2​NHN−CO−NH2​​→CH3​CH2​−CH=N−NH−CONH2​