April 28, 2024, 04:24:12 AM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Difficulty naming this rearrangement  (Read 4481 times)

0 Members and 1 Guest are viewing this topic.

Offline Eddzzz_2012

  • Regular Member
  • ***
  • Posts: 20
  • Mole Snacks: +1/-2
Difficulty naming this rearrangement
« on: February 12, 2013, 09:21:46 AM »
I'm having trouble naming this rearrangement so I know how to do the mechanism. Any help is appreciated. Cheers,

Ed
Logged

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
Re: Difficulty naming this rearrangement
« Reply #1 on: February 12, 2013, 01:04:49 PM »
Quote from: Eddzzz_2012 on February 12, 2013, 09:21:46 AM
I'm having trouble naming this rearrangement so I know how to do the mechanism

You would learn more by trying to figure out the mechanism, rather than trying to remember the name so you can just look it up.

KOH is a base, phthalimide is relatively acidic.
What kind of a reagent is Br2 (acid/base/electrophile/nucleophile?)
Logged
My research: Google Scholar and Researchgate

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Difficulty naming this rearrangement
« Reply #2 on: February 12, 2013, 06:03:57 PM »
It looks like a Hofmann rearrangement.
Logged
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
Re: Difficulty naming this rearrangement
« Reply #3 on: February 12, 2013, 07:03:53 PM »
Never mind...
Logged
My research: Google Scholar and Researchgate

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Difficulty naming this rearrangement
« Reply #4 on: February 13, 2013, 08:43:53 AM »
Quote from: Dan on February 12, 2013, 07:03:53 PM
Never mind...

I gave the name because I did not think it was obvious how the named reaction would lead to isatoic anhydride or anthranilic acid.
Logged
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Eddzzz_2012

  • Regular Member
  • ***
  • Posts: 20
  • Mole Snacks: +1/-2
Re: Difficulty naming this rearrangement
« Reply #5 on: February 13, 2013, 09:26:59 AM »
Cheers for the answers. I was thinking the Hofmann but I thought it was only for primary amides not secondary like this one, even though it has the same catalyst.
« Last Edit: February 13, 2013, 10:02:04 AM by Eddzzz_2012 »
Logged

Offline Eddzzz_2012

  • Regular Member
  • ***
  • Posts: 20
  • Mole Snacks: +1/-2
Re: Difficulty naming this rearrangement
« Reply #6 on: February 13, 2013, 10:50:33 AM »
so this means I have to convert this into a primary amide by attacking the carbonyl group with an OH.
Logged

Offline Eddzzz_2012

  • Regular Member
  • ***
  • Posts: 20
  • Mole Snacks: +1/-2
Re: Difficulty naming this rearrangement
« Reply #7 on: February 13, 2013, 12:41:52 PM »
Cheers, got this in the end!
Logged
Pages: [1]   Go Up
« previous next »
Sponsored Links