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Standard XII

Chemistry

Methods for Ester Synthesis

An organic co...

Question

An organic compound $^{'} A^{'}$ on treatment with ammoniacal silver nitrate gives metallic silver and produces a yellow crystalline precipitate of molecular formula $C_{9} H_{10} N_{4} O_{4}$ , on treatement with Brady's reagent. Give the structure of the organic compound $^{'} A^{'}$ .

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Solution

Since the organic compound $^{'} A^{'}$ reduces ammoniacal silver nitrate (Tollen's reagent), it must be an aldehyde. Moreover, with Brady's reagent (2, 4-dinitro phenylhydrazine) it gives a precipitate of molecular formula $C_{9} H_{10} N_{4} O_{4}$ , it must be propanal $(C H_{3} C H_{2} C H O)$ . The reactions are as follows.

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^{'} A^{'}

(molecular formula

C_{3} H_{8} O

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forms a shining silver mirror on warming with ammoniacal silver nitrate.

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(molecular formula

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forms a shining silver mirror on warming with ammoniacal silver nitrate.

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Q. An excess of 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 H₂NCONHNH_2,HCl and sodium acetate, it gives a product 'C'. Identify the structure of 'C'

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An organic compound ′A′ on treatment with ammoniacal silver nitrate gives metallic silver and produces a yellow crystalline precipitate of molecular formula C9H10N4O4, on treatement with Brady's reagent. Give the structure of the organic compound ′A′.

Since the organic compound ′A′ reduces ammoniacal silver nitrate (Tollen's reagent), it must be an aldehyde. Moreover, with Brady's reagent (2, 4-dinitro phenylhydrazine) it gives a precipitate of molecular formula C9H10N4O4, it must be propanal (CH3CH2CHO). The reactions are as follows.

An organic compound $^{'} A^{'}$ on treatment with ammoniacal silver nitrate gives metallic silver and produces a yellow crystalline precipitate of molecular formula $C_{9} H_{10} N_{4} O_{4}$ , on treatement with Brady's reagent. Give the structure of the organic compound $^{'} A^{'}$ .