oxidation to the next level

[SaintJude]

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the following rx converts ALL substituents into "COOH" groups..

For real???!

 

[syoung]

the following rx converts ALL substituents into "COOH" groups..

For real???!

http://en.wikipedia.org/wiki/Potassium_permanganate
Yep it's a strong oxidizing agent, and its in conc form. If it were dilute KMnO4, it wouldn't convert all to COOH.

 

[Jarudy]

For real.

 

[MedPR]

KMnO4 + heat is pretty badass.

 

[folktale]

That is amazing. And I love the "for real??" phrase haha.

 

[SaintJude]

http://en.wikipedia.org/wiki/Potassium_permanganate
Yep it's a strong oxidizing agent, and its in conc form. If it were dilute KMnO4, it wouldn't convert all to COOH.

Thank you for making the distinction about concentrated and dilute KMnO4.

Final "Key Concept" review after looking into this further:

cold, basic dilute:
adding alcohols to a double bond/ (syn addition so watch position of alcohols)

hot, basic solution of KMNO4 followed by acid wash (H+):

terminal alkenes --> ketone & CO2 -(I'm sure AAMC would like to trip people up who solely looking for a COOH as an answer choice)

nonterminal alkenes --> 2 molar equivalents of COOH

non-tertiary benzylic carbon (there has to be a hydrogen present on the benzylic C) --> COOH

(Still think it's amazing that an entire alkane chain gets converted into a COOH group)

source: http://masterorganicchemistry.com/r...-alkanes-with-kmno4-to-give-carboxylic-acids/