[Steenrod]

I was looking up my school question papers and one of the questions was:
"How would you distinguish between ethyl alcohol and 1-propanol using a chemical test?"

I hope someone would please tell me the answer.I have an exam in 4 days and the exam's syllabus is not rigorous(it does not discuss reaction mechanisms, so I am in a bit of trouble and the questions look ad hoc), so I am not able to solve this.
Thank you..

[Arkcon]

OK, but maybe you can use some reaction mechanisms from your class notes or textbook, to try to learn for yourself what possible reactions you'd find only in one or the other.  You might not find this exact problem on the exam, so it would be better for you if you tried to pick this problem apart.

[Rutherford]

You can do it with the haloform reaction, ethyl alcohol gets oxidized and it reacts with a hypohalite by the mechanism given here http://en.wikipedia.org/wiki/Haloform_reaction.

[manofohm]

There are certainly a seemingly unlimited amount of possible methods of testing chemically.

 The first 100% chemical test I can think of is to react in anhydrous conditions with phosphorus oxychloride (POCl3) followed by adding water if a layer forms on top you have n-propyl chloride if all the product left as a gas upon POCl3 reaction you have ethyl chloride.

Really, its all based upon the reactions that you have already been taught though.

[curiouscat]

 The first 100% chemical test I can think of is to react in anhydrous conditions with phosphorus oxychloride (POCl3) followed by adding water if a layer forms on top you have n-propyl chloride if all the product left as a gas upon POCl3 reaction you have ethyl chloride.

I hate these questions, they are so artificial: after reacting with POCl3 you are forced to eventually distinguish between a gas and a liquid; now that's a physical distinction.

Why not distinguish between a liquid and gas, with the pristine sample as it is. Just do it at, say 85 C.

/rant 

[discodermolide]

Sorry, but Raderford is correct. The haloform reaction is the way to go and it is a 100% chemical test.

[Steenrod]

Thank you Raderford.

[manofohm]

I dont know, I used to prepare chloroform for distribution and I tried every possibility for the production of it on a small scale at least. I seem to remember ethanol reacted really sluggishly with Ca(OCl)2 and NaOCl. I seem to remember however through my limited research involving POCl3 that the reaction was kind of quick and that the exitinguising of it would mearly be adding cold water to dissolve the phosphoric acid.

I think it would be a perfectly acceptable method for determining the alcohol with an undergrads knowledge of chemistry.

Hey but why couldnt you just use a GC.