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Why is the answer C? Can someone draw out a mechanism for how C and D work?
Difficult Chen MCAT question
- Thread starter SonhosDaVida
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If I remember correctly from orgo I, I think it's because KMnO4 is not specified as hot and concentrated. When it is cold and reacted with a base, it will form syn diols. If KMnO4 and H+ were to react with added heat, it would cleave and the resulting product would not be hexanoic acid. Although the question didn't specify conditions, I don't believe you would get hexanoic acid either way. Hopefully this helps. Someone please correct me if I'm wrong.
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(C) can only go to ketone. To get oxidized further carbon - carbon bonds would have to be broken.
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The option C, the double bond will be broken up and further oxidized into two carboxylic acid on two ends.
All other options will give you the target compound gradually.
All other options will give you the target compound gradually.
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2ketones or 2COOH?
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Canada to the rescue: https://home.cc.umanitoba.ca/~hultin/chem2220/Support/oxidative_cleavage.pdf
@hellocakes appears to be correct. C will produce two carboxylic acid groups on opposite ends of an alkyl chain, which would not be hexanoic acid.
The mechanism for D is that KMnO4 just oxidizes the hell out of the alkyne group. KMnO4 is a very strong oxidizing agent and appears to generally always progress to COOH if appropriate substrate material is available.
@hellocakes appears to be correct. C will produce two carboxylic acid groups on opposite ends of an alkyl chain, which would not be hexanoic acid.
The mechanism for D is that KMnO4 just oxidizes the hell out of the alkyne group. KMnO4 is a very strong oxidizing agent and appears to generally always progress to COOH if appropriate substrate material is available.
