Essay On The Synthesis Of 4-Methyl-2-Pentanol

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Oxidation of a Secondary Alcohol with Chromic Acid in Diethyl Ether to Produce a Ketone Compound

Amber Breakspear 15202075 – 12th January 2016
Year 1 Full Report 1 – Organic

Abstract
An effective oxidation of the secondary alcohol with chromic acid to produce the corresponding ketone. In this report the synthesis of 4-methyl-2-pentanone from 4-methyl-2-pentanol via an adapted jones oxidation1, using diethyl ether as the solvent and concentrated sulphuric acid, is described. An overall yield of 35.74 % was achieved and the product was characterised by NMR, IR and boiling point analysis.
Introduction
The conversion of an alcohol into a carbonyl compound is of great importance to the chemistry discipline. Oxidation of alcohols …show more content…

This takes place by addition of the alcohol oxygen to chromium, forming a zwitterion. Water removes a proton which is transferred to the chromate ester. After hydrolysis, the carbonyl compound is formed (fig.5). By limiting the amount of water and oxidant present in the reaction , the second oxidation can be stopped and an aldehyde forms (see fig 1 where R1 = H).3 Tertiary alcohols are resistant to oxidation because you need at least one alpha hydrogen attached to the carbinol …show more content…

Cr(VI) oxidants are able to oxidise any CH bonds on a carbinol carbon as far as possible and no carbon-carbon bonds are broken so allows for selective oxidation. They have strong oxidising power and consequently will oxidise both secondary alcohols to ketones and primary alcohols to carboxylic acids. An example of this is Jones reagent (see fig.2) which was discovered in and is typically a solution of chromium trioxide in dilute sulphuric acid and acetone. In some cases only the aldehyde is required so Cr(VI) oxidants are not required; therefore a weak oxidising agent, with milder conditions is useful such as pyridinium dichromate. 1’

Figure 2-Typical Jones oxidation of 1⁰ and 2⁰ alcohols
With uses of carbonyls ranging from flavouring agents to acting as intermediates to make pharmaceuticals, results and further research could have a potential impact on both the chemical industry and the public. In particular, the product formed in the experiment, 4-methy-2-pentone, is used for organic solvents and as a material used in the preparation of many chemical compounds and paints. 5

Materials and Experimental

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