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Kainui

  • 5 months ago

How does an arenium ion's resonance structure show us that it favors either ortho/para or meta directing? @Somy

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  1. Somy
    • 5 months ago
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    idk u explain lol ♥

  2. Kainui
    • 5 months ago
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    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!

  3. Kainui
    • 5 months ago
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    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.

  4. Somy
    • 5 months ago
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    AlCl3 +Cl2 --> im kinda confused

  5. Somy
    • 5 months ago
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    ohhh we put them into benzene ring?

  6. Somy
    • 5 months ago
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    oh ok i didn't know whats aniline

  7. Kainui
    • 5 months ago
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    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.

  8. Somy
    • 5 months ago
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    |dw:1403634997582:dw|

  9. Somy
    • 5 months ago
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    |dw:1403635104840:dw|

  10. Kainui
    • 5 months ago
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    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.

  11. Somy
    • 5 months ago
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    AlCl3 and Cl2 this reaction would be substitution right?

  12. Kainui
    • 5 months ago
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    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?

  13. Somy
    • 5 months ago
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    hmmm electrophilic that would mean electron wanting

  14. Somy
    • 5 months ago
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    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

  15. Kainui
    • 5 months ago
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    |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.

  16. Somy
    • 5 months ago
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    hmmm|dw:1403635465614:dw|

  17. Somy
    • 5 months ago
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    it looks like dative bonding

  18. Kainui
    • 5 months ago
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    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?

  19. Somy
    • 5 months ago
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    i remember NH2 and carboxylic group being meta director alright so nitro is also meta director

  20. Somy
    • 5 months ago
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    |dw:1403635624964:dw|

  21. Kainui
    • 5 months ago
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    NH2 is an ortho/para director, carboxylic acid is a meta director though.

  22. Kainui
    • 5 months ago
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    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.

  23. Somy
    • 5 months ago
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    eeeehh ok gimme a sec to refresh my memory

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