Kainui
  • Kainui
How does an arenium ion's resonance structure show us that it favors either ortho/para or meta directing? @Somy
Organic
  • Stacey Warren - Expert brainly.com
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SOLVED
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jamiebookeater
  • jamiebookeater
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Somy
  • Somy
idk u explain lol ♥
Kainui
  • Kainui
While I prepare, try to draw the mechanism of the reaction of aniline with AlCl3 and Cl2. I'm going to take a while to explain the mechanism behind the reaction so that you can work it out. I think being able to work out organic chemistry problems kind of like math problems is the best way. If this doesn't make sense, hopefully it will very soon!
Kainui
  • Kainui
You have two options. We can do the full mechanism for this reaction or we can simplify it so that we assume that AlCl3 and Cl2 really just puts Cl+ into solution for the aromatic ring to act as an electrophile.

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Somy
  • Somy
AlCl3 +Cl2 --> im kinda confused
Somy
  • Somy
ohhh we put them into benzene ring?
Somy
  • Somy
oh ok i didn't know whats aniline
Kainui
  • Kainui
Wait, I'm sorry I just realized that I made this reaction up on the spot, and doing the exact reaction I describe will fail. Aniline is the common name for aminobenzene.
Somy
  • Somy
|dw:1403634997582:dw|
Somy
  • Somy
|dw:1403635104840:dw|
Kainui
  • Kainui
Alright, now the problem with adding chlorine through using AlCl3 and Cl2 is that we'll instead make a salt that interacts with the lone electron pair on the nitrogen. So we're going to have to pick something else. In general what you might want to do is reduce a nitro group to an amine group. Which you can use metal and an acid. So instead lets start out with something else, I feel like I've needlessly confused you haha we'll do a better example. Nitrobenzene will be our starting compound and we'll react it with AlCl3 and Cl2 to add.
Somy
  • Somy
AlCl3 and Cl2 this reaction would be substitution right?
Kainui
  • Kainui
Yes, although it's not exactly a normal substitution as we'll see. It's not quite SN2 or SN1, instead we call it "Electrophilic aromatic substitution" and this is the subject of the lesson today. How does this substitution happen?
Somy
  • Somy
hmmm electrophilic that would mean electron wanting
Somy
  • Somy
so that means something that we are going to add has to want an electron and the benzene ring has to have that electron to donate
Kainui
  • Kainui
|dw:1403635189768:dw| Yep exactly. To test your knowledge, finish drawing the formal charges and bonds and electron pairs on the nitro group of nitrobenzene.
Somy
  • Somy
hmmm|dw:1403635465614:dw|
Somy
  • Somy
it looks like dative bonding
Kainui
  • Kainui
Nope, chlorine will only end up on the right side, I just mean draw the structure of nitrobenzene with charges and bonds shown. Chlorine will add to the meta position since nitro is a meta director right?
Somy
  • Somy
i remember NH2 and carboxylic group being meta director alright so nitro is also meta director
Somy
  • Somy
|dw:1403635624964:dw|
Kainui
  • Kainui
NH2 is an ortho/para director, carboxylic acid is a meta director though.
Kainui
  • Kainui
Here, let's start over I put too much information and now I think it's confusing you. Let's close this and start fresh.
Somy
  • Somy
eeeehh ok gimme a sec to refresh my memory

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