Question

Two compunds with the formula C4H8O,A+B, are run through test with the following results. predict the...

Two compunds with the formula C4H8O,A+B, are run through test with the following results. predict the structure of each.
A) A forms a silver mirror in the tollen's test but does not react to iodiform.
B) B forms a yellow precipitate with iodiform but does not react in the tollens test

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Answer #1

(A) Since A forms silver mirror in the tollen's test, it is aldehyde and it does not give iodoform test, so it does not contain CH3 - CO - group.

So, the compound 'A' is CH3CH2CH2CHO

CH3CH2HC2CHO + Ag2O --------> Ag (s) + CH3CH2CH2COOH

                        tollen's reagent           silver mirror

CH3CH2HC2CHO + I2 + NaOH -------> No reaction

(B) B froms yellow precipitate of iodoform.

CH3COCH2CH3 + I2 + NaOH ---------> CHI3 + CH3CH2COONa

                                                             Iodoform(yellow ppt.)

CH3COCH2CH3 + Ag2O (tolle's reagent) ---------> no reaction.

So, compound 'B' is CH3COCH2CH3

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