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O-xylene is a benzene ring with two methyl groups in the ortho-positions. Methyl groups on a benzene ring act as o,p-directors, which means that they direct electrophiles to the carbon directly across or directly beside the existing methyl group.

Friedel-crafts acylation creates the electrophile using a Lewis acid catalyst, however because there are two methyl groups side by side on o-xylene, the electrophilic addition is not as straightforward as described above. The two methyl groups direct the electrophile to different carbons, creating a mixture of products.

As a result, there will be two products formed:

One product will be a benzene ring with the electrophile and two methyl groups in a 1,2,3 orientation.

The second product will be a benzene ring with the electrophile and two methyl groups in a 1,3,4 orientation (respectively).

It is my understanding that the second product will be most predominantly formed, because it has the least steric hindrance (it is less crowded).

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Related Questions

What is friedal craft reaction?

when alkyle helide or acyle helide react with benzene ring and there is elemanition of h ATM such reaction called friedal craft reaction ............... there is 2 types 1...... friedal craft Alkylation 2...... friedal craft Acylation


In Freidal craft reactions what is the role of Lewis acids?

Lewis acids help in the generation of electrophiles in Friedel Crafts reactions.


What is the reaction mechanism for the synthesis of formyl ferrocene with triethyl orthoformate and AlCl3?

it's a friedel-craft acylation with the triethyl orthoformate being a formyl synthon. the AlCl3 is a Lewis acid, it coordinates the ethoxy group, which is kicked off by the adjacent oxygen. The ferrocene then is the nucleophile and the rest of the reaction is a standard electrophilic aromatic substitution leaving the formyl oxonium, which is quenched to the formyl on work-up. i think that's how it goes anyway, i haven't read the paper.


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