[GaryGlobetrotter]

..

[Coursework.info]

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[TiTo20]

(Original post by GaryGlobetrotter)
Help required

"For the following reactions predict and NAME the main products formed"

3. Ethyl methyl amine with cold Nitrous acid

4. Phenol with concentrated Nitric acid at room temp.

5. Methyl benzene with concentrated Nitric and concentrated Sulphuric acids at room temp.

6. But-2-ene with bromine water at room temp

7. Salicylic acid and Ethanoic anhydride at 85 degrees celsius

8. Propanamide with dilute Sodium hydroxide and pure Brominee Br2 at room temp and in the fume cupboard

Any help appreciated

Thanks

3. Ethylmethylnitrousamine

4. Most likely 4-nitrophenol, it can be 2-nitrophenol, but the nitro and hydoxyl groups will repel each other and make it less stable.

5. 2-nitromethylbenzene

6. This is weird, because the normal answer would be 2,3-dibromobutane, but you can have 3-bromobutan-2-ol as well, depending on whether there is a greater concentration of water or bromine molecules in the bromine water solution.

7. I know what it makes, I just don't know how to name it - Sorry! Just know that the ethanoic anhydride reacts with the hydroxy group on the salicylic acid.

8. The propanamide is hydrolysed by the NaOH... But I'm unsure as to what happens when Bromine is added. Sorry!

Hope this has helped, no matter how late it is =]


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[Jakelee]

Surely 7 is aspirin?

[Kyri]

(Original post by TiTo20)
8. The propanamide is hydrolysed by the NaOH... But I'm unsure as to what happens when Bromine is added. Sorry!

The reaction of an amide with Br2 and NaOH is called the Hofmann degradation. I don't think you need to know the mechanism for A level but basically you end up with an amine with one less carbon atom (which is lost as CO2). The product for that question would be ethylamine.

[TiTo20]

(Original post by Jakelee)
Surely 7 is aspirin?

I was trying to think of the ILPAC name for it, with 3% battery on my phone =P I also haven't done chemistry in a while since I finished with it in March... My bad =P

(Original post by Kyri)
The reaction of an amide with Br2 and NaOH is called the Hofmann degradation. I don't think you need to know the mechanism for A level but basically you end up with an amine with one less carbon atom (which is lost as CO2). The product for that question would be ethylamine.

I got wrecked! =[ +1 chem knowledge =P



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[thegodofgod]

(Original post by Jakelee)
Surely 7 is aspirin?

, I think

Acetylsalicylic acid, formed via nucleophilic addition-elimination

2-hydroxybenzoic acid + ethanoic anhydride ----> acetylsalicylic acid + ethanoic acid