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Topic: Permanganate Organic Reaction  (Read 8263 times)

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Chrataxe

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Permanganate Organic Reaction
« on: November 08, 2005, 03:18:39 AM »
Ok...we were told that they don't teach this reaction in entry level organic anymore but they used to.  When our teacher gave us our handout, it was on there.  He said if we could figure it out, we would get extra credit.  I'm having trouble finding the reaction....

CH3-CH2-CH=CH2 + MnO4(-)--->?

I've seen reactions dealing with acidic and basic conditions....but, that is all we are given.  Any ideas?
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Offline Borek

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Re:Permanganate Organic Reaction
« Reply #1 on: November 08, 2005, 04:05:06 AM »
Quote from: Chrataxe on November 08, 2005, 03:18:39 AM
CH3-CH2-CH=CH2 + MnO4(-)--->?
Any ideas?

Best idea always: Google double bond and permanganate.
« Last Edit: November 08, 2005, 04:11:31 AM by Borek »
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Offline movies

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Re:Permanganate Organic Reaction
« Reply #2 on: November 08, 2005, 11:31:53 AM »
Another idea is to think about any other reagents that you know that have a similar structure to MnO4- and think about the reactivity of those reagents.
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Offline fran008

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Re:Permanganate Organic Reaction
« Reply #3 on: November 08, 2005, 12:35:29 PM »
The reagent KMnO4 (conc and hot) is used to oxidise alkenes to determine position of C=C bond

CH3-CH2-CH=CH2 + MnO4(-)--->CH3-CH2CHO + CH2O
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Offline Borek

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Re:Permanganate Organic Reaction
« Reply #4 on: November 08, 2005, 12:53:07 PM »
Quote from: fran008 on November 08, 2005, 12:35:29 PM
->CH3-CH2CHO + CH2O

Are you sure the reaction stops here?
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Offline Alberto_Kravina

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Re:Permanganate Organic Reaction
« Reply #5 on: November 08, 2005, 01:00:04 PM »
Quote
->CH3-CH2CHO + CH2O

Are you sure the reaction stops here?

I think i t reacts so:

H3C-H2-CHO + H2CO ------> H3C-(CH2)2-COOH

I'm not totally sure about this...an aldehyde reacts with another to form an acid ???
« Last Edit: November 08, 2005, 01:00:41 PM by Alberto_Kravina »
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Offline Mitch

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Re:Permanganate Organic Reaction
« Reply #6 on: November 08, 2005, 01:26:33 PM »
The reaction turns an alkene into a diol if you work it up in aqueous solution.
« Last Edit: November 08, 2005, 01:26:53 PM by Mitch »
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Offline Albert

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Re:Permanganate Organic Reaction
« Reply #7 on: November 08, 2005, 01:38:08 PM »
Quote from: Chrataxe on November 08, 2005, 03:18:39 AM
CH3-CH2-CH=CH2 + MnO4(-)--->?
Yes, the product is a diol: CH3-CH2-CHOH-CH2OH...and MnO2

These are the conditions: T=0°C, pH = 7, solvent: pure water.

Please, pay attention: the OH groups are CIS.
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Offline HP

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Re:Permanganate Organic Reaction
« Reply #8 on: November 08, 2005, 02:20:53 PM »
The formed diol could ferder oxidize to corresponding propionate salt  CH3-CH2-COO:-K+ and HCOO-:K+ especially in heating. I am not sure if potassium formiate could ferder oxidise to CO2.
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Offline Mitch

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Re:Permanganate Organic Reaction
« Reply #9 on: November 08, 2005, 02:30:03 PM »
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