A compound of molecular formula C3H60 forms a yellow precipitate with 2,4-dinitr

Question

A compound of molecular formula C3H60 forms a yellow precipitate with 2,4-dinitrophenyl-hydrazine reagent and gives a silver mirror with Tollens' reagent. Based on this information, draw the structural formula for the compound. What should you see when the following compounds are mixed togethri with the given test solution? Pentanone and valeraldehyde (see Table 4) have close boiling points, 102 and 103 degree respectively. Suggest a way that these two compounds could be distinguished and identified. (A boiling point difference of 1 degree C is too close to measure experimentally.) Use laboratory tests from this experiment and show how you could distinguish between the compounds listed below. Suggest tests that give a clear, positive test result for the listed compound, but are unique to it and thus, different from the others.

Explanation / Answer

1) Since the compund gives yellow precipitate with 2,4-Dinitrophenylhydrazine it is either a alicyclic ketone or aldehyde. but it gives silver ppt. with tollen's reagent so it is a aldehyde. therefore its structure is CH3-CH2-CHO. 2)a) i) ketones gives yellow precipitate with 2,4-Dinitrophenylhydrazine. ii) methyl ketones give pale yellow precipitate with KI-I2 reagent iii)No silver colour because it ketones dont react with tollen's reagent

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