n the current experiment, we will use a different electrophile (the tert.-butyl cation) to alkylate 1,4-dimethoxybenzene. This is a Friedel-Crafts Alkylation reaction. LOCH3 (H;C);C. LOCH3 (CH3);COH CH;COOH/H,SO4 H;CO H;CO `C(CH3)3 The primary difference between Friedel-Crafts EAS reactions and other EAS reactions

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...
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Outline a mechanism for the formation of the compound. Please use software to draw the reaction 

 

In the current experiment, we will use a different electrophile (the tert.-butyl cation) to alkylate
1,4-dimethoxybenzene. This is a Friedel-Crafts Alkylation reaction.
LOCH3
(H;C);C.
LOCH3
(CH3);COH
CH;COOH/H,SO4
H;CO
H;CO
`C(CH3)3
The primary difference between Friedel-Crafts EAS reactions and other EAS reactions
(i.e., nitration, halogenation, etc.) is that in a Friedel-Crafts reaction (alkylation or acylation), the
electrophile is a carbon atom (i.e., in this experiment it is a tert.-butyl carbocation). In many cases,
the Friedel-Crafts electrophile is generated using a chlorine-containing molecule (i.e., an acyl
[acid] chloride or an alkyl chloride) and an appropriate Lewis acid (i.e., AlCl3, BF3) catalyst
(examples are shown below):
Acyl halide
8-
+ AlCl3
.AICI3
R
R
`Cl
8+
+ AICI4
A 11u1 helido
Transcribed Image Text:In the current experiment, we will use a different electrophile (the tert.-butyl cation) to alkylate 1,4-dimethoxybenzene. This is a Friedel-Crafts Alkylation reaction. LOCH3 (H;C);C. LOCH3 (CH3);COH CH;COOH/H,SO4 H;CO H;CO `C(CH3)3 The primary difference between Friedel-Crafts EAS reactions and other EAS reactions (i.e., nitration, halogenation, etc.) is that in a Friedel-Crafts reaction (alkylation or acylation), the electrophile is a carbon atom (i.e., in this experiment it is a tert.-butyl carbocation). In many cases, the Friedel-Crafts electrophile is generated using a chlorine-containing molecule (i.e., an acyl [acid] chloride or an alkyl chloride) and an appropriate Lewis acid (i.e., AlCl3, BF3) catalyst (examples are shown below): Acyl halide 8- + AlCl3 .AICI3 R R `Cl 8+ + AICI4 A 11u1 helido
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