Chemistry Homework Solutions
Problem
#8761

Alcohol Oxidation puzzle

We oxidized 2-ethyl-1,3-hexanediol with NaOCl.  3 products could be produced.  The product obtained was run through an IR spectrum (see attached).  2 of the possible products contain an OH and C=O while the 3rd contains 2 C=O functional groups.  With the 2 that contained an OH group, 1 had the C=O in an aldehyde position, while the other had the C=O in a ketone position.  From my spectrum, I know my product was one which contained an OH functional group.  My question is: From the spectrum, how do I know which product the spectrum represents?  The aldehyde-positioned C=O or the ketone-positioned C=O?  Aldehydes and ketones are in the same range on the spectrum, so I am confused.  We were given no other information, like chemical shifts or integrations.

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