Electrophilic Aromatic Substitution: NO2 & NO Groups

In summary, the NO2 group directs meta with-deactivation in electrophilic aromatic substitution, while the nitroso group (-NO or -ONO) directs ortho-para with-deactivation. The difference in behavior can be explained by the different resonance forms that these groups can take on in the aromatic ring. When a halide, such as bromine, is added to form p-bromonitrosobenzene, it directs ortho-para substitution while also deactivating the ring. This can be justified by considering both the electronic and steric effects of the halide on the aromatic ring.
  • #1
ddrplayboy
2
0
The NO2 group directs meta with-deactivation in electrophilic aromatic substitution. The nitroso group - NO directs ortho-para with - deactivation. Write out the electroinc structures of - NO2 and -NO and explain the differences in behavior. Show all pertinent resonance forms for the addition of bromonium ino to form p-bromonitrosobenzene.
thanks for looking
 
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  • #2
What is your question? We can't just answer your textbook question. What are you having trouble with in the problem?
 
  • #3
First off, nitroso is written as -ONO. Please show where you are stuck; if you don't understand anything, be sure to post your question after you have studied to understand our responses.
 
  • #4
Start by writing out the resonance structures for the aryl cation, "move the electrons around" as you have learned before, or should have. You should be able to notice why the nitroso group is supposed to direct ortho para ("supposed" since I haven't looked into this before). Ortho para with deactivation? doesn't ring a bell to me.
 
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  • #5
Halides like bromine on the aromatic ring will direct ortho/para while deactivating the ring as well. To justify this observation you will need to consider two different effects.
 
  • #6
chem_tr said:
First off, nitroso is written as -ONO. Please show where you are stuck; if you don't understand anything, be sure to post your question after you have studied to understand our responses.

Edit: Nitroso may also be in the form of N=O, as we are dealing with organic substances; inorganic nitroso compounds are written as -ONO.
 

Related to Electrophilic Aromatic Substitution: NO2 & NO Groups

1. What is electrophilic aromatic substitution?

Electrophilic aromatic substitution is a type of organic reaction in which an electrophile (a positively charged or electron-deficient atom or molecule) replaces a hydrogen atom on an aromatic ring.

2. What is the role of the NO2 group in electrophilic aromatic substitution?

The NO2 group, also known as a nitro group, is a strong electron-withdrawing group that can activate the aromatic ring towards electrophilic substitution. It does this by increasing the electron density in the ring, making it more susceptible to attack by electrophiles.

3. How does the NO group affect the reactivity of aromatic compounds in electrophilic substitution?

The NO group, also known as a nitroso group, is an electron-withdrawing group that deactivates the aromatic ring towards electrophilic substitution. This is because the nitrogen atom is highly electronegative and pulls electron density away from the ring, making it less reactive towards electrophiles.

4. What are some examples of electrophilic aromatic substitution reactions involving NO2 and NO groups?

Some common examples of electrophilic aromatic substitution reactions involving NO2 and NO groups include the nitration of benzene, the Friedel-Crafts reaction, and the Sandmeyer reaction.

5. How do the positions of the NO2 and NO groups on the aromatic ring affect the reactivity in electrophilic aromatic substitution?

The position of the NO2 and NO groups on the aromatic ring can greatly impact the reactivity in electrophilic aromatic substitution. Generally, groups located in the ortho and para positions (relative to the electrophile) will increase reactivity, while groups in the meta position will decrease reactivity.

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