Author Topic: Simple question (curiosity) (Read 1976 times)

Jubrail · « **on:** July 05, 2003, 05:59:00 AM »

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.

Osmium · « **Reply #1 on:** July 05, 2003, 06:42:00 AM »

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

Jubrail · « **Reply #2 on:** July 05, 2003, 07:35:00 AM »

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

acid_egg · « **Reply #3 on:** July 05, 2003, 07:45:00 AM »

http://www.chem.leeds.ac.uk/delights/texts/Demonstration_09.htm

...and you may have some problems retrieving the product.

Jubrail · « **Reply #4 on:** July 05, 2003, 08:13:00 AM »

Definitely appreciated. I can now sleep at night.

News:

Author Topic: Simple question (curiosity) (Read 1976 times)

Jubrail

Simple question (curiosity)

Osmium

1. NaNO2/H(+) ----> diazonium compound 2.

Jubrail

Thanks, Os

acid_egg

the one pot low yield method

Jubrail

Thanks