Chemistry Forums for Students > Problem of the Week Archive

Problem of the week - 13/05/2013

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Borek:
Organic compounds X (molar mass 26 g/mol) and Y (60 g/mol) react in the presence of catalyst, yielding compound Z (86 g/mol). Z decolorizes bromine water, but it doesn't react with ammoniacal solution of disilver oxide. Left in acidic solution Z undergoes hydrolysis, and products of the reaction don't react with bromine water, but they do react with the ammoniacal solution of silver dioxide, producing silver mirror on the test tube surface (plus ammonium acetate). What are compounds X, Y and Z, and what are the reaction equations? Please use SMILES for answers.

iamback:
Please also mention the level of question. Like I am a high school student, I am not able to solve it, even though it looked like I would be able to solve it. I spent half and hour on it, and  was only able to get some clues.

I have studied everything which the question mentions, but I think it's difficult.

Any hint.

Borek:
Definitely HS, can be difficult if you have not taken any organic chemistry yet.

kriggy:
Man this one is good. I think I have it, so lets see:
compound X -
compound Y -
which together in catalyzed by acid
gives compound Z -

Which undergoes adition of Br2 (aq) on double bond

but esters arent reduced by Tollen´s reagent.
By hydrolysis we got acetic acid

and ethene-1-ol
which is unstable and by keto-enol tautomery isomerizes to acetaldehyde
which reduces Tollens reagent but doesnt react with bromine water.
__
btw HS? And I thought we had good chemistry teacher at grammar school. I couldnt solve it with only my HS chemistry.

Borek:
HBr?

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