Oxidation of Borneol

04-24-2013

Exp. 7 Oxidation of Borneol

The purpose of this experiment is to convert the secondary alcohol Camphor to the ketone – Borneol in the following oxidation reaction –

This reaction can be completed with different reagents which are quite effective but most of them are quite toxic and this is not good in a lab environment. According to the lab manual we are to use sodium hypochloride – house bleach. This is so because it is a safe substance to use, as well as readily available and not costly. There will also be an evaluation of the melting point which will be taken after the product’s IR has been taken using special machinery. The IR will help us understand the accuracy of our product to see if the reaction was successful. The melting point will help with the recognition of the correct presence based on the original melting point to the product.

Observation and result –

the IR evaluation showed the following wavelength values present –

i. 1285.82

ii. 1742.09

iii. 2298.34

Our result was satisfactory to the purpose of the experiment because we had very good results throughout the lab. The TLC was a good way to evaluate our result; the product was a little short on the RF with only .375 but this is because this is more polar compared to the original because of the structure. The moiré polar a substance is, the less distance it travels up the TLC plate. The percentage yield calculation is the following –

The melting point found for the sample was C and it is quite close to the reference point of 176 C. The IR values show the correct peaks representing what should be represent. This is discussed in more detail below.

*these results were not from our group, we made the foolish mistake of throwing the sample away before having the opportunity to dry it and evaluate its MP to corroborate the rest of the results*

1. Interpret the IR spectra peaks

i. 1285.82 – not major carboxylic acid –...