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Topic: lab re: id of unknown ketone/aldehyde  (Read 5419 times)

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a_b_possibly_c

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lab re: id of unknown ketone/aldehyde
« on: October 14, 2005, 11:16:14 AM »
Okay, I know the lab of "Identify the Unknown functional group,aldehyde, ketone, etc." is the rites of passage for any o. chem. student.  I have been successful in id/classifications in the past.  However, I have somehow missed the mark on this one, big time.  The classification test for this lab are Tollens Silver Mirror Test, Schiff Test, Iodoform test, and semicarbazone derivative comparison. Unfortunetly my under-funded school has no way of measuring refractive index as indicated in the lab. My "qualitative" results are as follows:  
Tollens test: + for mirroring, no ppt when comparing it to o-tolualdehyde, the lab instructor (who did not actually hand out the unknown, his pretentious disorganized lackey did), marked it wrong.

Schiff test: - when comparing it to the aforementioned known positive hmmm.

Iodoform test: - again when comparing it to the same known +

mp (degree centigrade): 189, wrongo according to the lab instructor should have been 195

my conclusion based on lit. was a very unpure 2-furaldehyde, or cyclohexane-carbaldehyde, with the possibility of a false + Schiff test.  I realize that I should have repeated this EXPT. again, to rule-out questionable results, but time is of the essence.
His conclusion was that my unknown was 2-methylcyclohexanone. WHAT?!?

At last my question is, shouldn't the Iodoform test, testing for a methyl ketone, have been clearly positive?  Also why would I have had unmistakable + mirror testing results after Tollens test?  Any help/explaination is helpful, the lab instructor is not open to discuss this, he is right and I am wrong.

thanks, wb  

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Re:lab re: id of unknown ketone/aldehyde
« Reply #1 on: October 14, 2005, 11:24:42 AM »
There is no way that you have 2-methylcyclohexanone.  It would be a liquid at room temperature.

a_b_possibly_c

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Re:lab re: id of unknown ketone/aldehyde
« Reply #2 on: October 14, 2005, 11:33:04 AM »
oops sorry I guess I should have listed observed physical properties.
 
clear, liquid at room temp (sorry about that), bp 165-195 celsius

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Re:lab re: id of unknown ketone/aldehyde
« Reply #3 on: October 14, 2005, 05:13:50 PM »
Oh...it said mp in your first post.

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