Why do an substitution rather than EAS?

[deleted862553]

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Can someone help me understand question 269 on the Destroyer?

An acetyl chloride reacts with anilene. Why does a substitution occur rather than a EAS reaction? I thought the amide would add the acetyl group to the o or p position

 

[averageasian]

no, an acyl chloride is highly reactive with amines. You would need an acid catalyst to power the addition of the acyl group to the ring, such as AlCl3.

 

[NextStepTutor_2]

Hi AARM,

The amino group on aniline is nucleophilic like other amines and therefore preferentially reacts during acylation. Acylation is even used to protect the amino group and to make aniline less reactive during other EAS reactions. A brief review of aniline reactions is shown here:
http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ref/ch22arylamines.html