Jubrail (Hive Bee)
07-05-03 05:59
No 444680
      Simple question (curiosity)  Bookmark   

This is an orgo. theory question:

If I have a benzene ring with NH2 attached and want to replace this with COOH:

 _           _
/ \_NH2 --> / \_COOH
\_/         \_/

I believe that the text book way to do this is to convert the molecule to a disulfide salt with NaNO2 and HCl, then use Cupric Cyanide / Potassium CN to change it into a benzen ring with a CN on it.  Then it can be reacted in an acidic aqueous solution to get the desired molecule.

First off, is this correct?  Secondly, is there another route that can be used? 

No, I am not a college orgo student, that needs help on his homework.  I am an ignorant man trying to teach myself some chemistry.

Rainbows & Butterflies Forever :)
(Stoni's sexual toy)
07-05-03 06:42
No 444685
      1. NaNO2/H(+) ----> diazonium compound 2.  Bookmark   

1. NaNO2/H(+) ----> diazonium compound
2. React with CuCN ----> benzonitrile
3. hydrolyse to produce the acid

I'm not fat just horizontally disproportionate.
(Hive Bee)
07-05-03 07:35
No 444690
      Thanks, Os  Bookmark   

But my question was if that was the only path to the final compound?

Rainbows & Butterflies Forever :)
(Hive Addict)
07-05-03 07:45
No 444693
      the one pot low yield method  Bookmark   


...and you may have some problems retrieving the product.tongue
(Hive Bee)
07-05-03 08:13
No 444697
      Thanks  Bookmark   

Definitely appreciated.  I can now sleep at night.

Rainbows & Butterflies Forever :)