Reactions of Aromatic Compounds Flashcards
How is aromaticity regained?
By the loss of a proton.
Name 5 reactions of electrophilic aromatic substitution.
Halogenation
Nitration
Sulfonation
Friedel-Crafts alkylation
Friedel-Crafts acylation
Explain halogenation.
Replacement of H (on benzene) by Br or Cl.
Explain nitration.
Replacement of H (on benzene) by NO2.
Explain sulfonation.
Replacement of H (on benzene) by SO3H.
Explain Friedel-Crafts alkylation.
Replacement of H (on benzene) by R.
Explain Friedel-Crafts acylation.
Replacement of H (on benzene) by RCO.
Give the 2-step mechanism of all electrophile aromatic substitution reactions.
- Addition of the electrophile to form resonance stabilized carbocation
- Followed by deprotonation with base
Is bromination of benzene exothermic or endothermic?
Exothermic
What compound is used most often as a catalyst in chlorination?
AlCl3 (FeCl3 will also work).
What catalyst is used in nitration? And what does it react with?
Sulfuric acid (H2SO4); HNO3
Sulfuric acid is used as a catalyst in nitration for…
the reaction to be faster and at lower temperatures.
Toluene reacts ___ times faster than benzene.
25
Why are ortho and para attacks preferred in nitration reactions?
Because their resonance structures include one tertiary carbocation.
Are nitro groups activators or deactivators?
Deactivators.
NO2 is also called a…
meta director.
Electrophilic substitution reactions for nitrobenzene are how many times faster/slower than what?
100,000 times slower than benzene.