Arrange the compounds by their reactivity toward electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward
electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward electrophilic aromatic substitution.

General guidance

Concepts and reason
The concept used to solve this problem is the concept of (electrophilic aromatic substitution). The electrophilic aromatic substitution represents an organic reaction, which is characterized by the replacement of an atom attached to the aromatic ring (usually benzene) by an electrophile.

Fundamentals

In the , the aromatic ring (usually benzene) acts as a nucleophile and replaces a substituent atom with an electrophile. It means benzene tends to donate electrons from inside its ring. Thus, benzene become less reactive in the when electron-withdrawing groups (deactivating groups) are attached with it. On the other hand, the ring become more activating towards the when electron-donating group is attached with it.

Step-by-step

Step 1 of 2

The functional group present in the aniline and toluene activates the ring toward . On the other hand, the functional group attached with the fluorobenzene, nitrobenzene and acetophenone deactivates the ring towards the .

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The group attached with the ring represents an electron-donating group in the case of aniline. Similarly, the group attached with the ring in the case of toluene also represents an electron-donating group. These electron-donating groups activates the ring towards the .
The group attached with the ring represents an electron-withdrawing group in the case of fluorobenzene. Similarly, the group associated with the nitrobenzene and the acetyl group associated with the acetophenone represent an electron-withdrawing group. These electron-withdrawing groups deactivates the ring towards the .

The electron-withdrawing and electron-donating groups can be mistaken. This mistake can be avoided by properly studying the concepts of electrophilic aromatic directing groups properly.

The order of reactivity depends on the degree of activating the benzene ring.

Step 2 of 2

The compounds can be sorted by their reactivity towards electrophilic aromatic substitution in the following order:

The compounds can be sorted by their reactivity towards the in the following order:

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The group attached with the ring in the case of aniline represents an electron-donating group and donates electrons through resonance, which makes the benzene ring more reactive towards the . The group present in the toluene donates electron through its bond, thus activates the ring towards the . However, the electron donating tendency of aniline is more as compared to that of toluene.
Benzene is an aromatic compound with no substituents attached. Thus, it is more reactive towards electrophile as compared to the aromatic compounds, which have electron withdrawing substituents but less reactive than the aromatic compounds with electron donating substituents.
The group attached with the ring in the case of fluorobenzene, fluorine represents an electron-withdrawing group. This group weakly deactivates the ring towards the . The acetyl group associated with the acetophenone is also an electron-withdrawing group and moderately deactivates the ring. Lastly, the group associated with the nitrobenzene represents a strong electron-withdrawing group, thus, deactivates the ring very strongly.

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The order of reactivity towards the can be mistaken. This mistake can be avoided by studying the concepts of the properly.

Answer

The compounds can be sorted by their reactivity towards the in the following order:

Answer only

The compounds can be sorted by their reactivity towards the in the following order:

(-NH,)
(-CH,)
(-NO2)
(-COCH)
Most Reactive NH, CH Least Reactive
(-NH,)
(-CH,)
(-COCH)
(-NO2)
Most Reactive NH, CH Least Reactive
Most Reactive NH, CH Least Reactive
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Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution. Sort the following compounds by their reactivity toward
electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution.

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