[Sush_eera]

Can someone help me with this organic question. i have a chem exam next week. so this is about preparation of methyl red ( an azo compound) from benzene
 so this is what i tried:
1. convert benzene to nitrobenzene by adding HNO₃ / conc. H₂SO₄ at 50^oC
2. later, convert the nitro benzene into an amine benzene by adding Sn/CHCl
3. The convert amide Benzene into diazonium salt by adding NaNo₃and HCL at 5^oC
 
I dont know what to do to form a azo compound after converting the Benzene to a diazonium salt. Can some one help? pleaseee.. This is the question

[orgopete]

You need to look up how to form the diazo bond. That will suggest the route for the preparation.

[Sush_eera]

You need to look up how to form the diazo bond. That will suggest the route for the preparation.

yes I do know how to form a diazonium bond but i cant seem to figur out what happens after the diazonium bond is formed.. like how to get to the sturcture shown in the picture.

[critzz]

If you don't know how to make the azo-functionality, then how do you know you need to make a diazonium compound first? 
Anyways, if I remember correctly you can literally find the reaction in Clayden's organic chemistry book (search for a diazo-coupling or diazonium salt).

1. convert benzene to nitrobenzene by adding HNO₃ / conc. H₂SO₄ at 50^oC
2. later, convert the nitro benzene into an amine benzene by adding Sn/CHCl
3. The convert amide Benzene into diazonium salt by adding NaNo₃and HCL at 5^oC

How and when would you introduce the carboxylic acid moiety?

[orgopete]

yes I do know how to form a diazonium bond but i cant seem to figur out what happens after the diazonium bond is formed.. like how to get to the sturcture shown in the picture.

The route having been suggested gives a "diazonium salt". It can react in a characteristic way to give a diazo bond as shown for the dye. Most textbooks show this. Again, I suggest looking it up. Hint, dimethylaniline is one of the needed reactants.

[CKabes]

1. Make toluene with CH3Cl and AlCl3
2. Nitrate while you still have an o/p director
3. Oxidize the toluene with KMnO4
4. Reduce the amine with SnCl2
5. Make the diazonium salt with NaNO2Cl
6. Couple with dimethylanaline