In Friedel-Crafts acylation, why is water needed? Why does the entire step 4 mechanism need to occur?   Also in the step 4 mechanism, what are the exact arrow-pushing mechanisms for the addition of water?

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In Friedel-Crafts acylation, why is water needed? Why does the entire step 4 mechanism need to occur?

 

Also in the step 4 mechanism, what are the exact arrow-pushing mechanisms for the addition of water? 

MECHANISM 17-6 Friedel-Crafts Acylation
Friedel-Crafts acylation is an electrophilic aromatic substitution with an acylium ion acting as the electrophile.
Step 1: Formation of an acylium ion.
acylbenzene
î
R-C -AICI,
R C 1: + AlCl3 →
acyl chloride
complex
acylium ion
Steps 2 and 3: Electrophilic attack forms a sigma complex, and loss of a proton regenerates the aromatic system.
(+)
C
ofkoeleno
R
H
Cl AICI₂
H
sigma complex
R
+ AlCl3
AICI4+ [R
[R-C=O
(+)
acylbenzene
Step 4: Complexation of the product. The product complex must be hydrolyzed (by water) to release the free acylbenzene.
ĀIC13
Dod
R
product complex
R + AlCl3
+
HC1
excess H₂O
R-C=0:]
R
free acylbenzene
+ aluminum salts
Transcribed Image Text:MECHANISM 17-6 Friedel-Crafts Acylation Friedel-Crafts acylation is an electrophilic aromatic substitution with an acylium ion acting as the electrophile. Step 1: Formation of an acylium ion. acylbenzene î R-C -AICI, R C 1: + AlCl3 → acyl chloride complex acylium ion Steps 2 and 3: Electrophilic attack forms a sigma complex, and loss of a proton regenerates the aromatic system. (+) C ofkoeleno R H Cl AICI₂ H sigma complex R + AlCl3 AICI4+ [R [R-C=O (+) acylbenzene Step 4: Complexation of the product. The product complex must be hydrolyzed (by water) to release the free acylbenzene. ĀIC13 Dod R product complex R + AlCl3 + HC1 excess H₂O R-C=0:] R free acylbenzene + aluminum salts
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