Question

In: Chemistry

through a mechanistic analysis of the electrophilic aromatic substitution of acetamidobenzene, explain why this compound mainly...

through a mechanistic analysis of the electrophilic aromatic substitution of acetamidobenzene, explain why this compound mainly substitutes mainly para. Suggest a reason why the reaction rate of acetamidobenzene with electophiles is slower than the rate of the reaction of aniline with electrophiles.

Solutions

Expert Solution

  1. Acetamido group is electron donationg and so it is ring activating.
  2. Acetamido group is ortho or para directing.
  3. There is pumped electron density by acetamido group attached to the benzene ring.
  4. This electron density is accumulated at ortho and para positions.
  5. Now acetamido group is bulky it obstructs the incoming electrophile attacking at ortho positions.
  6. para position in acetamidobenzene (acetanilide) is more free comparatively, to be attacked by electrophile in electrophylic substitution of acetamido benzene.
  7. if the incoming or attacking group is also bulkier then the electrophile without any hesitations attacks the para positopns. only
  8. So steric hidrance is the main role player in deciding the para postions in acetamido benzene and electrophylic substution occurs mainly at para positions comparitive to ortho position is acetamidobenzene.

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  1. amino group and acetamido group both are electron donating and ring activating groups.
  2. Amino group is more strong electron donating group than acetamido group.
  3. so the rate of electrophylic substituion is slower in acetamido benzene than aniline.
  4. The electron density on nitrogen atom is dragged by the more electronegative atom oxygen in R-(c=o)-NH (acetamido group).Rimg activation becomes slow in acetanilide.Also incoming eletrophile is hindered by bulkier acetamido group
  5. By the time electrophile orients itself to the attacking site in acetanillide , the reaction completes in aniline.

Aatawlide


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