Complete the mechanism for the generation of the electrophile used for Friedel-Crafts acylation with the following…
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Question “Complete the mechanism for the generation of the electrophile used for Friedel-Crafts acylation with the following…”
Complete the mechanism for the generation of the electrophile
used for Friedel-Crafts acylation with the following acyl halide.
Add curved arrows, bonds, electron pairs, and charges where
indicated.
Answer
This question was solved by the concept of describing the mechanism for formation of electrophiles in Friedel Crafts acylation reaction. The reaction of acyl halid with Lewis acids such as {\rm{Al}}{{\rm{X}}_{\rm{3}}} creates the electrophile in Friedel-Crafts’ acylation reaction.
Friedel-Crafts Acylation: This is an aromatic electrophilic substitution reaction. This reaction involves the addition of Lewis acids to the acyl halide. The reaction of acylhalide and Lewis acids such as {\rm{Al}}{{\rm{X}}_{\rm{3}}} creates the electrophile.
The reaction of acetyl chlorineide with {\rm{FeC}}{{\rm{l}}_{\rm{3}}} results in the formation of the electrophile acetylium Ion.
Mechanism for a Reaction: This diagram shows the process of a reaction. Curved arrows are used in this diagram to show the electron flow. A curved arrow shows the location of electrons coming from, while the tail indicates where they are going.
The tail of the curving arrow should be placed on either an electron-rich or bond, and the head must be placed upon the electron deficient. The moment electrons change from an electron-rich to an electron-poor state is represented by the curved arrows.
Given,
The structure of acid chloride (butyryl chlorineide) can be found here:
The Lewis acid is $math_tag_2
The first step in the mechanism is the curved arrow. It goes from an electron richer, more electronegative chlorine atom to an electron deficient Fe-atom of {\rm{FeC}}{{\rm{l}}_{\rm{3}}}.
You can write the first step by putting the curving arrow from a chlorine atom to a Fe atom. This step sees the single pair of electrons from chlorine move to an empty orbital of Fe at {\rm{FeC}}{{\rm{l}}_{\rm{3}}}.
The second step of this mechanism also draws its curved arrow from C-Cl bond electrons to electron deficient Cl atoms. This equation is available.
You can write the second step by drawing a curving arrow connecting bond pair electrons in C-Cl bond with electron deficient Cl.
The electron-deficient carbonyl carbon is able to give $math_tag_6 and acylium Ion.
You can write the second step of this mechanism as follows:
Ans Part A
Below is the curved arrow that will lead to the first step in the mechanism.
Part B
Below is the structure of species as well as the curve arrow for step two of the mechanism.
Part C
The species structures formed in the second stage of the mechanism are the following:
Conclusion
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