Week 14: Electrophilic Aromatic Substitution Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system Cl2 .CI (usually hydrogen) is replaced by an electrophile. FeCl, This is a two-step reaction mechanism with a carbocation intermediate. First step: Aromatic rings (like alkenes) can also act as nucleophiles. The clectrons of the ring are only attracted to very strong electrophiles. Ci--Ci--FeCla H. FeCla What mechanism does this resemble? What is the nucleophile? What is the electrophile? What is the role of the FeCl3? ond cto linte ronidlur dergoe elimination to reform the

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I think I understand most of this except for what mechanisms these resemble. Thanks!
Week 14: Electrophilic Aromatic Substitution
Electrophilic aromatic substitution is an organic reaction
in which an atom that is attached to an aromatic system
(usually hydrogen) is replaced by an electrophile.
CI
FeCl,
This is a two-step reaction mechanism with a carbocation
intermediate.
First step: Aromatic rings (like alkenes) can also act as nucleophiles. The electrons of the
ring are only attracted to very strong electrophiles.
H
CI
Ci-CI--FeCla
Fecl.
What mechanism does this resemble?
What is the nucleophile?
What is the electrophile?
What is the role of the FeCl3?
Second step: The cationic intermediate rapidly undergoes elimination to reform the
aromatic ring.
.CI
CI -FeCl3
What mechanism does this resemble?
Why does this step occur so rapidly? What is the driving force?
Transcribed Image Text:Week 14: Electrophilic Aromatic Substitution Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. CI FeCl, This is a two-step reaction mechanism with a carbocation intermediate. First step: Aromatic rings (like alkenes) can also act as nucleophiles. The electrons of the ring are only attracted to very strong electrophiles. H CI Ci-CI--FeCla Fecl. What mechanism does this resemble? What is the nucleophile? What is the electrophile? What is the role of the FeCl3? Second step: The cationic intermediate rapidly undergoes elimination to reform the aromatic ring. .CI CI -FeCl3 What mechanism does this resemble? Why does this step occur so rapidly? What is the driving force?
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