June 25, 2024, 02:01:32 PM
Forum Rules: Read This Before Posting


Topic: Correct reaction?  (Read 2710 times)

0 Members and 1 Guest are viewing this topic.

Offline rentj

  • New Member
  • **
  • Posts: 8
  • Mole Snacks: +0/-0
Correct reaction?
« on: May 01, 2024, 02:13:29 AM »
I was learning about ketones and aldehydes until I found this in the book. Isn't the third step supposed to be MCPBA or any peroxy acid? Thank you.

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2243
  • Mole Snacks: +151/-10
Re: Correct reaction?
« Reply #1 on: May 01, 2024, 03:14:03 AM »

You get an aldehyde from the ozonolysis, do you suggest that this can be oxidized to carboxylic acid with a peroy acid?

Offline Meter

  • Full Member
  • ****
  • Posts: 261
  • Mole Snacks: +14/-5
  • Take what I say with a grain of salt
Re: Correct reaction?
« Reply #2 on: May 06, 2024, 07:20:42 AM »

You get an aldehyde from the ozonolysis, do you suggest that this can be oxidized to carboxylic acid with a peroy acid?
Is Bayer Villager not plausible?

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2243
  • Mole Snacks: +151/-10
Re: Correct reaction?
« Reply #3 on: May 07, 2024, 12:30:13 AM »

Offline Meter

  • Full Member
  • ****
  • Posts: 261
  • Mole Snacks: +14/-5
  • Take what I say with a grain of salt
Re: Correct reaction?
« Reply #4 on: May 07, 2024, 05:59:37 AM »
That would give you an ester? From a ketone?

https://en.wikipedia.org/wiki/Baeyer%E2%80%93Villiger_oxidation#cite_note-named-1
Literature is shaky on this because no one in their right mind would oxidize benzaldehyde with BV to yield benzoic acid. Seems like the 'aldehyde' ester needs a bit more exotic reagents than just peroxyacids (Natu, A. D., Burde, A. S., Limaye, R. A., & Paradkar, M. V. (2014). Acceleration of the dakin reaction by trifluoroacetic acid. Journal of Chemical Research, 38(6), 381-382. doi:https://doi.org/10.3184/174751914X14014814873316). Didn't take time to read it thoroughly.

For the record OP, can you think of a way that step 2 could yield the final product?

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2243
  • Mole Snacks: +151/-10
Re: Correct reaction?
« Reply #5 on: May 07, 2024, 08:40:40 AM »

You can do it in just one step with permanganate, it's not a very good scheme

Sponsored Links