1997_1997
Badges: 0
Rep:
?
#1
Report Thread starter 5 years ago
#1
Hey guys,

I'm struggling with this question, I'm meant to make this compound of an azo-dye (picture attached) starting from Benzene.

This is what I've done so far, please help.

Thanks 😊

Attachment 469521469523
Attached files
0
reply
InadequateJusticex
Badges: 18
Rep:
?
#2
Report 5 years ago
#2
(Original post by 1997_1997)
Hey guys,

I'm struggling with this question, I'm meant to make this compound of an azo-dye (picture attached) starting from Benzene.

This is what I've done so far, please help.

Thanks 😊

Attachment 469521469523
The substitution part of your working out is not incorrect, but it's not very practical as you'd need to do this under vigorous conditions. If you wish to make phenol from benzene you'd have to go through the diazonium ion to do that (make nitrobenzene, reduce to phenylamine, convert to diazonium ion, etc)
0
reply
Pigster
Badges: 19
Rep:
?
#3
Report 5 years ago
#3
Also, you go from phenol to benzoic acid by oxidation, but there is an extra carbon atom in benzoic.

Which spec are you doing?
0
reply
Sunshine98
Badges: 8
Rep:
?
#4
Report 5 years ago
#4
Start with benzene
Nitrate it (add NO2 group) to make nitrobenzene
Reduce it (so the NO2 group becomes an NH2 group) to form a phenyl amine
Then the NH2 changes into NA+Cl- which I have no idea how but that's the azo dye derivative

Sorry, hope it helps a bit
0
reply
charco
Badges: 17
Rep:
?
#5
Report 5 years ago
#5
(Original post by 1997_1997)
Hey guys,

I'm struggling with this question, I'm meant to make this compound of an azo-dye (picture attached) starting from Benzene.

This is what I've done so far, please help.

Thanks 😊

Attachment 469521469523
You wish to make an azo-dye you need to make a diazonium salt and react it with a phenol derivative, so it looks like you will need to make two different reagents, the hydroxybenzoic acid as well as the diazonium salt.

If you're starting with benzene the diazonium salt is made by nitration (conc. sulfuric and nitric acid) followed by reduction (tin and HCl) to make phenylamine. Then you react phenylamine with nitrous acid (sodium nitrite and HCl) below 5ºC. This makes phenyldiazonium chloride.

A sample of phenol made by allowing the some of the diazonium salt to heat up above can be acylated (AlCl3, ethanoyl chloride) in a Freidel Crafts reaction and then hydrolysed to make the hydroxycarboxylic acid.

This will then react with the diazonium salt to form the azo-dye
0
reply
X

Quick Reply

Attached files
Write a reply...
Reply
new posts
Back
to top
Latest
My Feed

See more of what you like on
The Student Room

You can personalise what you see on TSR. Tell us a little about yourself to get started.

Personalise

Do you have the space and resources you need to succeed in home learning?

Yes I have everything I need (87)
64.44%
I don't have everything I need (48)
35.56%

Watched Threads

View All
Latest
My Feed

See more of what you like on
The Student Room

You can personalise what you see on TSR. Tell us a little about yourself to get started.

Personalise