OC help!

[Emmie]

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I'm working on kaplan OC ST 3 and I believe the ans key is wrong but I want to get your opinion.

benzene with 3 substituents...

1) COOH
2) ethyl
3) propenyl

solvent: KMnO4 (conc.) with heat

predict the product

 

[Valigator00]

I'm working on kaplan OC ST 3 and I believe the ans key is wrong but I want to get your opinion.

benzene with 3 substituents...

1) COOH
2) ethyl
3) propenyl

solvent: KMnO4 (conc.) with heat

predict the product

Do you get 3 carboxylic acids? I think that is the answer. IM not sure.

 

[Emmie]

I was taught that alkyl group can't be converted with KMnO4.

The ans key said benzene with 3 COOH groups! ??? 😕

 

[Valigator00]

I was taught that alkyl group can't be converted with KMnO4.

I thought that it could if it was attached to benzene. Am I correct though?

 

[yumi43]

if the alkyl substituent attached to the benzene ring has a benzylic hydrogen, the entire thing will be oxidized into a COOH group. it doesn't matter how long the chain is, as long as a benzylic H is present, it will turn into COOH. that said, it won't work for a tert-butyl substituent (no benzylic hydrogens). i hope this makes sense!

 

[NumbaOneStunna]

This is slightly off topic but can KMNO4 do dihydroxylation on an Alkene? I saw this in Topscore, never seen it used as a reagent this way - was wondering if its true and what other oxidizing agents do this as well. The only reagent i was aware of that did this was OsO4. Also is it true that dihydroxylation is not affected by sterics? There's a problem on topscore that says this and I wanted to make sure.

 

[yumi43]

This is slightly off topic but can KMNO4 do dihydroxylation on an Alkene? I saw this in Topscore, never seen it used as a reagent this way - was wondering if its true and what other oxidizing agents do this as well. The only reagent i was aware of that did this was OsO4. Also is it true that dihydroxylation is not affected by sterics? There's a problem on topscore that says this and I wanted to make sure.

in my kaplan book, it says KMnO4 will produce vicinal diols on alkenes only if it's a "cold, dilute, aqueous KMnO4". it's with syn orientation.