Chapter 18- Reaction of Aromatics (Part I)
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Electrophilic Aromatic Substitution
The addition of a strong electrophile to a ring.
Examples of Electrophilic Aromatic Substitution
-Halogenation -Nitration -Sulfonation -Alkylation -Acylation
The three steps of Electrophilic Aromatic Substituion
Step 1: Formation of electrophile (E+), aka Super Electrophile. Step 2: Attack on electrophile forms the sigma complex. This makes a C-E bond. (Slow step, high activation energy (Ea). Step 3: Loss of a proton gives a substitution aromatic product. (Fast step).
Reactants for Nitration
-Benzene ring -HNO3 -H2SO4
How do you make a nitronium ion? (Hint: Draw it out!)
How is a nitro group reduced? What molecule is attached to the benzene ring now?
To reduce a nitro group use Zn, Sn or Fe in HCl and then use NaOH. This then forms an NH2 group on the benzene ring.
What is an alternative to reducing a nitro group without the transition metals?
H2 and Pd/C or Pt (if you have money lol)
What reactants are needed for the bromination of a benzene?
-Br2 -FeBr3 or AlBr3
Provide the preliminary step of a bromination of a benzene. (Hint: Draw it out!)
Can fluorination occur with benzene?
No, the reaction is too violent.
Reactants of Iodination
-1/2 I2 -HNO3
What are the reactants of Sulfonation?
-SO3 (Sulfur Trioxide) -H2SO4
Write out the mechanism and product for the following reaction:
Write out the mechanism and product for the following reaction:
What reactants are involved in desulfonation?
-Benzenesulfonic acid -H2) -H+ -Heat