Would you please go through this link.

https://www.organic-chemistry.org/synthesis/C2O/ketones/oxidationsalcohols.shtm

Abdelkader BOUAZIZ delkader

thanks but my question isn’t about alcohols

Chromate ion:

Article Fluorenones Formation via Effective Chromium(VI) Oxidation i...

Article Chromium(VI) Oxide-Catalyzed Benzylic Oxidation with Periodic Acid

Dear Sharbel Damouni, sorry for the incorrect attached link. I have attached varied possibilities and choices to perform such an Oxidation. My Regards

https://www.organic-chemistry.org/synthesis/C2O/ketones/oxidationsbenzyls.shtm

https://www.masterorganicchemistry.com/2018/06/13/reactions-on-the-benzylic-carbon-bromination-and-oxidation/amp/

https://doi.org/10.1021/ol300853z

DOI:10.1039/C8CC08768G

Pyridinium chlorochromate

Chromic Acid (H2CrO4)

Nagaraju Karre Any source or book that shows that? it's not an alcohol.

I found it here : http://reag.paperplane.io/00000209.htm

but can you direct me to a book that elaborates it? Thanks!!

Hiteshkumar Gajjar I found some sources that show as been said that it can as we use acetic acid or acetic anhyride as a solvent, but chromic acid alone wont oxidize it fully to COOH and not a ketone? A source would help

Appreciate the help

2,2-Bipyridinium Chlorochromate

Shaema Kh. Mohamed Appreciate it, any source of the reactions of that reagent?

https://www.google.com/url?sa=t&source=web&rct=j&url=https://patents.google.com/patent/US4399281A/en&ved=2ahUKEwj9vdv-_8HmAhUtxaYKHUqiCjgQFjADegQIARAB&usg=AOvVaw0SXKhfeJIeddg_A7rjuR4q&cshid=1576768698115

Hi;

Sodium bichromate/glacial acetic acid mixture.

My regards

Doufnoune RACHIDA Rachida Thanks professor, may i know the purpose of glacial acetic acid? my thought is that it would make the reaction less violent so it wont lead to full oxidation to COOH. but how does it do that?

Hi Sharbel;

Glacial acetic acid is a good solvent for sodium bichromate.

With my best regards

Doufnoune RACHIDA Rachida

Thanks again.

but just to make my confusion clearer, there is a reaction that involves a benzylic carbon with hydrogen reacting with strong oxidizing agents like kmno4 and sodium bichromate to form carboxylic acid, I just wonder why in the case of fluorene it would stop at the ketone.

i really appreciate the help

Hi Sharbel;

In organic chemistry, potassium dichromate is a milder oxidizer than sodium permanganate.

In KMnO4, Manganese is in an oxidation state of (+7), reason why the KMnO4 is a strong oxidizing agent (the elements become more electronegative as the oxidation states of their atoms increase). In addition, the most powerful oxidant will have the highest standard reduction potential (E0). For the (Mn+7/Mn+2 you have E0 = +1.51 V).

MnO4- (+7) + 8H+ + 5e-® Mn2+ (+2) + 4H2O

In Na2Cr2O7, Bichromate is in an oxidation state (+6), For (Cr+6/Cr+3), E0 = +1.33 V.

Cr2O72- (+6) + 14H+ + 6e- ® 2Cr3+ (+3) + 7H2O

This is why the oxidation of fluorene by the Na2Cr2O7/CH3COOH mixture (mild conditions) ends at the stage of the carbonyl function.

With my best regards

You can carry out the oxidation of benzylic carbon to a ketone by DDQ, Chloroform, containing little water under reflux or DDQ aqueous acetoneat r.t . Alternately the oxidation can be carried out with DDQ/moist acetic acid under reflux. This is a method published by Prof. R.G.Harvey (in J. Org. Chem.) and works well in good yield.

Reference is attached bellow:

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in acetic acid, a convenient new reagent for the synthesis of aryl ketones and aldehydes via benzylic oxidatio

Hongmee Lee, Ronald G. Harvey ; J. Org. Chem. 1988, 53, 19, 4587-4589 [doi.org/10.1021/jo00254a035]

In an another method Bimal K. Banik et.al have used the reagent NaBiO3/ AcOH, to oxidize benzylic compound to a ketone (specially to diaryl ketones eg. fluorene derivatives to fluorenone derivatives).