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 AcylationFriedel-Crafts acylation is an electrophilic aromatic substitution with an acylium ion acting as the electrophile.Step 1: Formation of an acylium ion.acylbenzeneîR-C -AICI,R C 1: + AlCl3 →acyl chloridecomplexacylium ionSteps 2 and 3: Electrophilic attack forms a sigma complex, and loss of a proton regenerates the aromatic system.(+)CofkoelenoRHCl AICI₂Hsigma complexR+ AlCl3AICI4+ [R[R-C=O(+)acylbenzeneStep 4: Complexation of the product. The product complex must be hydrolyzed (by water) to release the free acylbenzene.ĀIC13DodRproduct complexR + AlCl3+HC1excess H₂OR-C=0:]Rfree acylbenzene+ aluminum salts

We have to explain the role of water in Friedel-Crafts acylation product. Also, we have to give the…

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?

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?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter15: Benzene And Aromaticity

Section15.SE: Something Extra

Problem 52AP

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Question

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

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