Professional Documents
Culture Documents
Lab 2 Orgo Lab Report
Lab 2 Orgo Lab Report
The objective of this lab was to perform an oxidation reaction and determine different
regioselectivities from different oxidants. In order to see how this can happen, we will use
different reagents to see how they oxidize alcohols to carbonyl compounds. Using my selected
oxidant, which was aqueous NaOCl in Acetic acid, and the starting material, 2-ethyl-1,3-
hexanediol, we were to observe whether both, one, or neither one of the two hydroxyl groups in
the starting material formed a carbonyl, and if one did, to determine which hydroxyl group
converted using H-NMR. The two hydroxyl groups form a primary alcohol and a secondary
The final yield of my product was 0.14g, making my percent yield to be 30% of what was
expected to be (0.47g) This loss could have occurred due to loss during transferring or mistakes
such as possible loss from incomplete extraction. My conclusion from the results of my IR and
H-NMR analysis is that the end product created was structure B, 3-(hydroxymethyl)heptan-4-
one.
My IR spectrum indicated that there was both an -OH group, due to the broad peak around
~3500-3600 cm-1. This can rule out the possibility of both hydroxyl groups reacting to become
carbonyl, therefore ruling out Structure C, if assuming that there was no starting material left
over. There was also a peak around 1700 cm-1 , although smaller than expected, therefore
proving that the reaction did in fact react and that one of the OH groups had reacted.
The NMR spectrum of my product had extra peaks that were to be ignored, including an acetone
peak at ~2.17 ppm, and a chloroform peak at 7.29 ppm, along with the usual TMS peak at 0 ppm.
The two possibilities that were left for me to consider was structure A, where if a carbonyl
formed at where the primary alcohol had occurred, would create an aldehyde. Also to consider, if
the carbonyl was formed at the secondary alcohol, the product would form instead a carboxylic
acid. Due to the absence of the usual aldehyde peak that would typically form at around 9-10
ppm, I ruled out the possibility of structure A, leaving the choice to be structure B, where it
formed a carboxylic acid. However, It is still unclear due to the fact typical peaks that would
have been seen for a carboxylic acid were missing as well, namely the OH peak at around 10-
12. Peaks that matched with the original product could suggest that starting material was still