Question #386fb

1 Answer
Jun 13, 2015

A para directing group directs incoming electrophiles to the para position of a benzene ring. A meta directing group directs incoming electrophiles to the meta position of a benzene ring.

Explanation:

Ortho-para directors

Groups with unshared pairs of electrons, such as the methoxy group of anisole and the amino group of aniline, are ortho-para directing.

Through resonance, they donate those unshared electrons to the π system.

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This puts extra electron density on the ortho and para carbons and makes them more attractive to an attacking electrophile.

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When the electrophile attacks the para position of aniline, the nitrogen atom can donate electron density to the π system.

This gives four resonance structures, as opposed to three if the #"NH"_2# group were absent.

This further stabilizes the cationic intermediate, lowers the activation energy, and increases the reaction rate.

So groups like #"CH"_3"O"# and #"NH"_2# are ortho-para directing groups.

Meta directors

Groups with double and triple bonds, such as nitro groups, are meta directing.

Through resonance, they remove electrons from the π system.

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This removes electron density from the ortho and para carbons.

The meta carbons have higher electron density, so they are more attractive to an attacking electrophile.

So groups like #"NO"_2# are meta directing groups.