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#1 2010-03-23 02:29:34


Potassium permanganate oxidation of an alkene

Yahoo!Answers in chemistry wrote:

Organic alkene synthesis with KMnO4?
In a basic solution it will form a diol, but in acid, will it form an aldehyde, a carboxylic acid or a keytone?

What will 2-butene form with KMnO4?

A: A carboxylic acid or a ketone. See the example below.

At higher temperatures, the manganate ester (A) will decompose with cleavage of the C-C bond. If the double bond contains a hydrogen atom, then the oxidation will con- tinue to a carboxylic acid. In the example, an intermediate aldehyde is formed. This can add water and form another manganate ester from the hydrate-OH. This ester will decompose to a carboxylic acid. The oxidation forms hydroxide which forms the salt of the carboxylic acid, therefore, a step in a permanganate oxidation, if heated, must be a neutralization step. If it is the final step, then neutral impurities can be easily removed.

So, for 2-butene, it will form two moles of acetic acid.


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