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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Hubert on November 19, 2005, 11:27:03 AM

Title: how oxidation work in hydrocarbon in the presence of KMnO4
Post by: Hubert on November 19, 2005, 11:27:03 AM
how oxidation work in hydrocarbon in the presence of KMnO4. For e.g this.
cyclohexene + KMnO4 = cis-1,2-cyclohenanediol


i tot oxidation onli works when it removes one hydrogen atom from a hydroxyl grp attached to the carbon and another hydrogen attached to the same carbon...so how does this work from this equation i wrote above
Title: Re:difficult question...i need help
Post by: FeLiXe on November 19, 2005, 11:57:33 AM
cis means they are both on the same side

you go through a cyclic ester

you end up with Mn(V) in MnO3- (which will disproportionate and react again)
Title: Re:difficult question...i need help
Post by: Arsenic on November 19, 2005, 12:25:01 PM
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fwww.ipfw.edu%2Fchem%2F262%2FImage1837.gif&hash=67499815183969d980c2eafda15587558e2bd742)
Title: Re: how oxidation work in hydrocarbon in the presence of KMnO4
Post by: Mitch on November 19, 2005, 12:41:44 PM
Hubert: Spell check your posts and write better topic subjects or be banned. Review forum policy on how to write subjects titled "Read This Before Posting!"
Title: Re: how oxidation work in hydrocarbon in the presence of KMnO4
Post by: Hubert on November 19, 2005, 09:06:54 PM
hey...ok...now this is the part...oh...where did the hydrogen come from....how cum it attaches to the oxgen atom form nowhere
Title: Re: how oxidation work in hydrocarbon in the presence of KMnO4
Post by: Hubert on November 19, 2005, 09:10:14 PM
and to what i learn in class...oxidation only involve the lose of a hydrogen attached to the carbon and a hydrogen of a hydroxyl grp attached to the same carbon...then how did oxidation work in the above diagram...sorrie...i'm realli confused
Title: Re: how oxidation work in hydrocarbon in the presence of KMnO4
Post by: Arsenic on November 19, 2005, 10:38:30 PM
see if this sheds any light on things
Title: Re: how oxidation work in hydrocarbon in the presence of KMnO4
Post by: Hubert on November 20, 2005, 02:41:58 AM
i mean with only cyclohexene and pottaium permanganate...how do they oxidise to becum an alcohol?
Title: Re: how oxidation work in hydrocarbon in the presence of KMnO4
Post by: Albert on November 20, 2005, 12:12:40 PM
To quote the poet, 'Water,water, water, nor any drop to drink!'

Water plays its role in this reaction by 'giving' H-atoms to the diol. Arsenic posted a complete mechanism for this reaction, where you can appreciate how water 'completes' the diol.
Not only does water take part in the reaction: also OH- does it!

However, if you want to see the electrons moving, look at the arrows (every arrow is a couple of electrons)