Chemistry, 14.01.2020 23:31 diontna29

As the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens. p-nitroaniline, for example, is planar. write a resonance contributor for p-nitroaniline that shows how the nitro group increases electron delocalization.

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Answer from: unkown77

As the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens. p-Nitroaniline, for example, is planar. Write a resonance contributor for p-nitroaniline that shows the nitro group increases electron delocalization:

This happen due to electron-withdrawing effect of Nitro group

see the attached in the image

Explanation:

What are delocalized electrons ?

The electrons present in a molecule which are not associated with a singlke atom or bond .

In benzene Ring electrons are declocalized because elctrons can be found equally on any of the six- carbons

How to show delocalization of electron ?

1. Electron moves towards positive charge atom or away from electron-rich atom

2. The movment of electron is shown by the arrow

3. Any group which stablise the excess charge, will increase the delocalization

Delocalisation of Aniline : look at the attached image

In free - NH3 group , The electron Pair (lone pair) of Nitrogen are easily available for donation and NH3 act as base. It has pyramidal shape

But in aniline ( one H of NH3 is replaced by the benzene ring ):

lone-pair of Nitrogen are deloclized over the benzene ring. Hence NH2- group become planar (flattened) and comes in the plane of benzene. The lone pair of electrons increase the electron density at ortho and para position of the benzene ring .

In p-Nitroaniline

Nitro(NO2)- group is present at the para position with respect to -NH2 This NO2- group is electron withdrawing in nature.Electron - withdrawing : those groups that draws the electron density towards themself . Hence they stablise the negative charge.NO2- stablises the increased electron density created by -NH2 of aniline . Hence it increases the electron delocalization
As the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens.

As the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens.

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As the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens....

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