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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Eddzzz_2012 on February 12, 2013, 09:21:46 AM

Title: Difficulty naming this rearrangement
Post by: 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. Any help is appreciated. Cheers,

Ed
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Title: Re: Difficulty naming this rearrangement
Post by: Dan 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?)

Title: Re: Difficulty naming this rearrangement
Post by: orgopete on February 12, 2013, 06:03:57 PM

It looks like a Hofmann rearrangement.

Title: Re: Difficulty naming this rearrangement
Post by: Dan on February 12, 2013, 07:03:53 PM

Never mind...

Title: Re: Difficulty naming this rearrangement
Post by: orgopete 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.

Title: Re: Difficulty naming this rearrangement
Post by: Eddzzz_2012 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.

Title: Re: Difficulty naming this rearrangement
Post by: Eddzzz_2012 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.

Title: Re: Difficulty naming this rearrangement
Post by: Eddzzz_2012 on February 13, 2013, 12:41:52 PM

Cheers, got this in the end!