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Topic: Can Someone please clear the aromatic oxidation issue?  (Read 303 times)

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Offline sharbeldam

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Can Someone please clear the aromatic oxidation issue?
« on: February 09, 2020, 02:03:26 PM »
I've honestly looked it up everywhere online and tried to search in the organic chem books in the library, it doesnt say anything about the products of these organic chemistry 2 reactions.
It is known that alkyl chain gets oxidized  to COOH if it was benzylic, but what about such cases? (Last two)

some site did say that acetophenone does get oxidized to benzoic acid but shouldn't the benzylic carbon contain atleast 1 hydrogen for this reaction to happen in O-chem 2?

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Offline hollytara

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Re: Can Someone please clear the aromatic oxidation issue?
« Reply #1 on: February 09, 2020, 02:57:52 PM »
So this is relevant:

https://hal.archives-ouvertes.fr/hal-01099843/document

For the first example (the cyclic structure with one tertiary on the benzene ring) - there are a variety of possible products since the hydroperoxide can form at any position.

Offline AWK

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Re: Can Someone please clear the aromatic oxidation issue?
« Reply #2 on: February 09, 2020, 04:00:52 PM »
Acetophenone reacts with KMnO4/H+ giving benzoic acid
For 1,1-dimethyltetraline my guess is dicarboxylic acid + 1 molecule of CO2
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Offline sharbeldam

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Re: Can Someone please clear the aromatic oxidation issue?
« Reply #3 on: February 09, 2020, 04:20:12 PM »
AWK, correct me please if I'm wrong, The benzyl ketone oxidizes to benzoic acid because of the enol formation which has a double bond that can be oxidized(cut) and hence forms a benzoic acid, It doesn't have to do with the benzylic carbon oxidation since it has no hydrogens right?

About the cyclic compound, (1,1-dimethyltetraline as you called it), can you please inform me how you think, if you oxidize the upper benzylic carbon to COOH (benzylic carbon oxidation since it has hydrogens), what happens to the lower alkyl chain since it cant be oxidized by that specific reaction.

- Holly thanks you for the reference, Ill give it a read.
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Offline AWK

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Re: Can Someone please clear the aromatic oxidation issue?
« Reply #4 on: February 09, 2020, 05:42:05 PM »
I reasoned by analogy. Since tetralin gives phthalic acid and carbon atoms without hydrogen do not oxidize, such a product may be formed. In the milder condition, you can expect tetralone.
AWK

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