1. Tardigrade
  2. Question
  3. Chemistry
  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'.

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Q. Compound '$A$' (molecular formula $C_3H_8O$ ) is treated with acidified potassium dichromate to form a product '$B$' (molecular formula $C_3H_6O$) '$B$' forms a shining silver mirror on warming with ammoniacal silver nitrate. '$B$' when treated with an aqueous solution of $H_2NCONHNH_2$ and sodium acetate gives a product -$C$ Identify the structure of '$C$'.

IIT JEEIIT JEE 2002Alcohols Phenols and Ethers

Solution:

$A$ is an alcohol and its oxidation product gives Tollen's test, i.e. $B$ must be an aldehyde $(CH_3CH_2CHO)$.
$CH_3CH_2CHO + \underset{\text{semicarbazide}}{H_2NHN - CO - NH_2} \rightarrow CH_3CH_2 - CH = N -NH - CONH_2$