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Question

An organic compound A with molecular formula C2H7N on reaction with nitrous acid gives a compound B. B on controlled gives compound C. C reduces Tollen's reagent to given silver mirror and D. B reacts with D in the presence of concentrated sulphuric acid to give sweet smelling compound E. Identify A,B,C,D and E. Give the reaction of C with ammonia?

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Solution

The compounds A,B,C,D and E are ethyl amine C2H5NH2 , ethanol C2H5OH, ethanal CH3CHO, ethanoic acid CH3COOH and ethyl acetate CH3COOC2H5.
Ethylamine on reaction with nitrous acid gives ethanol.
C2H5NH2HNO3−−−C2H5OH
Ethanol on controlled oxidation gives acetaldehyde.
C2H5OHcontrolled oxidation−−−−−−−−−−−CH3CHO
Acetaldehyde reduces Tollen's reagent to given silver mirror and ethanoic acid.
CH3CHO+2[Ag(NH3)2]++3OHheatCH3COO+2Ag+2H2O+4NH3
Ethanol reacts with ethanoic acid in the presence of concentrated sulphuric acid to give sweet smelling compound ethyl acetate.
C2H5OH+CH3COOHconc sulphuric acid−−−−−−−−−−CH3COOC2H5
The reaction of ethanal with ammonia is as shown in image.
626451_599068_ans_1ca0870e6a5a479e861c3b9c0de55c9a.png

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