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Topic: How does the reaction occur  (Read 1941 times)

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Offline Steenrod

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How does the reaction occur
« on: October 21, 2012, 01:48:27 AM »
When cyclohexene is treated with potassium permanganate and sulphuric acid and heated,the product is Hexane-1,6-dioc acid.I am unable to understand how the reaction occurs. Can anyone please explain how it takes place?Thanks.
I am horrible at chemistry.I am always liable to fail my chemistry exams.So, sorry for stupid questions.

Offline discodermolide

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Re: How does the reaction occur
« Reply #1 on: October 21, 2012, 04:59:42 AM »
Development Chemists do it on Scale, Research Chemists just do it!
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Offline orgopete

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Re: How does the reaction occur
« Reply #2 on: October 21, 2012, 09:00:48 AM »
There are several reagents that act similarly, osmium tetroxide, periodate, and permanganate. You can write a cyclic reaction that is similar to a Diels-Alder reaction when OsO4 reacts with a double bond. The product does not react further. Periodate does not react with an alkene, but it can react with a diol from the osmium reaction to give a similar structure to the osmium intermediate. The difference between these is the periodate structure will undergo a cyclic reversion which cleaves the C-C bond to give two carbonyl groups and reduces the iodine. The osmium intermediate does not cleave the C-C bond and must be hydrolyzed to obtain a diol.

Permanganate will perform both steps if heated. (Cold permanganate can be used to isolate a diol as an alternate to OsO4.) It will add to a double bond as OsO4 does and cleave the C-C bond as periodate does. The product will be two C=O bonds. If these are aldehydes, as they are from cyclohexene, they are also very easily oxidized, and permanganate can also react as an oxidant. It will oxidize the aldehydes to carboxylic acids.
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