DAT DESTROYER Org. #10

[Denizen]

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Since an R group is an ortho/para director, why doesn't an ortho product show up in this solution?

Also, I have never seen K2Cr2O7/H3O+ in my Chad's Videos review. Does is always perform the same reaction 1. KMnO4, OH-, ∆ 2. H3O+ would (i.e. benzylic oxidation)?

Thanks!

 

[Mrhyde]

Since an R group is an ortho/para director, why doesn't an ortho product show up in this solution?

Also, I have never seen K2Cr2O7/H3O+ in my Chad's Videos review. Does is always perform the same reaction 1. KMnO4, OH-, ∆ 2. H3O+ would (i.e. benzylic oxidation)?

Thanks!

EAS reactions , Benzilic Oxidation , which can be done by Chromic Acids or KMNO4 . I actually remember it being in chads videos . The give away when looking at this problem is noticing first 1) it can be an EAS reaction since there is benzene and 2) the Cr2O7 part looks like a version of Chromic Acid .

"Since an R group is an ortho/para director, why doesn't an ortho product show up in this solution?"

--> It does and it did and you drew it 🙂 ... The BR added Para to the R group on the EAS ............................... THEN sepeartley in the next step , Ortho/Para/Meta does not apply at all anymore since its just straight benzilic oxidation.

 

[DAT Destroyer]

Since an R group is an ortho/para director, why doesn't an ortho product show up in this solution?

Also, I have never seen K2Cr2O7/H3O+ in my Chad's Videos review. Does is always perform the same reaction 1. KMnO4, OH-, ∆ 2. H3O+ would (i.e. benzylic oxidation)?

Thanks!

The ortho isomer does indeed form, by is the minor product. For this reaction, I would estimate the ortho isomer as being 15%, but we normally don't need to show the minor products. To oxidize a side chain, the two methodologies you have referenced are the most common.

Hope this helps.

Dr. Romano