Will acetyl chloride react with the amino or aromatic part of aniline?

[thereddevils]

Homework Statement

Give the structural formula of the organic product formed from the following reaction:

CH3COCl + C6H5NH2

Homework Equations

The Attempt at a Solution

The ethanoyl chloride will break into CH3CO(+) and Cl(-) due to polarity. Then, which part of the aminobenzene will the electrophile attack?

 

[zorro]

I don't think you can conclude that ethanoyl chloride will break by itself. We can't use a Lewis acid for this purpose as it will react with aniline.

If you somehow break the compound, the electrophile will attack at ortho-para positions as aniline group is a ring activator (infact the reaction will be very vigorous and it over-reacts to form a tri substituted compound).

 

[Borek]

I don't think ring will be involved.

 

[thereddevils]

Thanks, so what's the correct mechanism for this? Borek, could you pls elaborate on that?

 

[Borek]

Just googling for aniline and acyl chloride should give you the correct answer.

 

[zorro]

Borek, could you pls elaborate on that?

Lol...do you expect Borek to elaborate? He always writes one liners