Sanzida Taslim

February 01, 2017

Experiment 02: Selectivity: Oxidation 1 vs 2 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

alcohol in the starting material.

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

present in my product, although unclear how much of it exactly was present.