science bump

I know you won't be able to help but i need to determine which alcohol group(s) (the primary, secondary or both) in 2-ethyl-1,3-hexanediol becomes oxidized when NaOCl in acetic acid is used as the oxidizing agent by looking at the infrared spectrum of the final compound. After pulling my hair out for about an hour and examining my IR i believe it was the secondary alcohol but that is only an educated guess. Thanks for the response though.

@Bocephus said:

When I took organic chem 1 the easiest thing for me was to commit all the absorption energies to memory. Once you know the absorption range of carbonyls, double bonds, triples bonds, etc.. you can compare it with the actual spectrum and recognize the patterns in the peaks of each type of bond. Eventually you'll be able to look at a compound and know immediately the types of peaks that the spectrum will have. I wasnt a fan of IR so some of my logic might be confusing.

Not confusing at all. I definitely have a broad alcohol peak so that eliminates both of them getting oxidized. So its between a keytone with a primary alcohol and an aldehyde with a secondary alcohol. I haven't been able to locate the actual IRs of the two compounds and they're very similar compounds so I have to use the fingerprint region to determine which one it is. I've used some websites to compare the peaks of aldehydes and keytones (b/c my text book doesn't go into much detail about the fingerprint regions) but I wasn't able to get a definitive answer on which one it is and don't wanna screw up my results/discussion/conclusion. Contradicting what I mentioned above I meant to say I believe it is the keytone with a primary alcohol but that is only a guess. It would have helped if I would have selected to print where the peaks are located (cm-1) on my print off.

Yeah IR only made sense if i had nmr data w it...its been so long! I believe aldehydes and ketones have distinct numbers associated around the 1700? range so that should be easy. Same with primary and 2° alcohols at whatever range. Dont psych yourself out w the graphs (which is what i used to do. Make an educated giess based off the nimbers you have, dont think too much

Edit: remember highest energy bonds are at the left and decrease in energy as you go to the right

This might help:

http://soundcloud.com/demoralize-unique/01-i-am-a-filter-next