How many nitrated products would you get from the nitration of methylbenzene?
The nitration of methylbenzene (toluene)
You get a mixture of mainly two isomers formed: 2-nitromethylbenzene and 4-nitromethylbenzene.
Why does methylbenzene react faster than benzene?
Methylbenzene is more reactive than benzene because of the tendency of the methyl group to “push” electrons towards the ring. The effect of this greater reactivity is that methylbenzene will react with fuming sulfuric acid at 0°C, and with concentrated sulfuric acid if they are heated under reflux for about 5 minutes.
Does methylbenzene react with nitric acid?
Reacting methylbenzene with a mixture of concentrated nitric and sulphuric acids gives both 2-nitromethylbenzene and 4-nitromethylbenzene. The mechanism is exactly the same as the nitration of benzene.
What will be the products of nitration of chlorobenzene?
Nitration of chlorobenzene gives ortho nitro chloro benzene and para nitro chloro benzene .
What can be made by nitrating Methylbenzene?
You get a mixture of mainly two isomers formed: 2-nitromethylbenzene and 4-nitromethylbenzene. Only about 5% of the product is 3-nitromethylbenzene.
Is no2 meta directing?
These positions are then deactivated in the direction of electrophilic aromatic substitution. Hence, as we all discovered in organic chemistry, NO2 is a meta-director.
Why reactivity of NO2 benzene is slow in comparison to benzene?
Notice that nitrobenzene is less reactive than benzene because the nitro group is a deactivating substituent. Notice also that meta-substitution reactions on nitrobenzene are faster than para-substitution reactions because the nitro group is a meta-directing group.
Which is the most reactive in electrophilic substitution?
Hence, the electron density on benzene ring is maximum in aniline. Hence, aniline is the most reactive towards electrophilic aromatic substitution.
What is the role of h2so4 in nitration of benzene?
In the protonation of nitric acid by sulfuric acid, the source of the nitronium ion induces the removal of a water molecule and the creation of a nitronium ion. The first step in benzene nitration is to activate HNO3 with sulfuric acid to create a nitronium ion, a stronger electrophile.
Which reagent is used in nitration of chlorobenzene?
The reaction of chlorobenzene with nitric acid in the presence of concentrated sulphuric acid is as shown in the diagram. Was this answer helpful?
What is the electrophile in nitration of chlorobenzene?
The electrophile is the “nitronium ion” or the “nitryl cation”, NO+2.
Is NO2 meta directing?
What is the mechanism of nitration?
The mechanism for nitration of benzene:
Step 1: Nitric acid accepts a proton from sulphuric acid and then dissociates to form nitronium ion. Step 2: The nitronium ion acts as an electrophile in the process which further reacts with benzene to form an arenium ion.
Is NO2 activating or deactivating?
The nitration of aniline is going to be faster than the nitration of nitrobenzene, since the aniline is a ring with NH2 substituent and nitrobenzene is a ring with NO2 substiuent. As described above NH2is an activating group which speeds up the reaction and NO2 is deactivating group that slows down the reaction.
Why is NO2 a deactivating group?
Since NO2 is an electron withdrawing group, a glance at the resonance structures shows that the positive charge becomes concentrated at the ortho-para positions. Thus these positions are deactivated towards electrophilic aromatic substitution. Hence, NO2 is a meta-director, as we all learned in organic chemistry.
Does NO2 deactivate benzene ring?
Correct Option d deactivates the ring towards electrophilic substitutionExplanation: – NO2 group withdraw electron from the ring thus shows -M effect and makes ring more electron deficient. Hence – NO2 deactivates the ring tor elctrophilic substitution.
Which is least reactive in electrophilic substitution?
Benzenesulphonic acid is least reactive in an electrophilic aromatic substitution due to −M effect.
Which is most reactive towards electrophilic nitration?
Here, toluence is most reactive towards electrophilic nitration as the presence of methyl group induces electron donating effect which increases the electron density.
Why is sulfuric acid a catalyst for nitration?
The formation of a nitronium ion (the electrophile) from nitric acid and sulfuric acid is shown below. The sulfuric acid is regenerated and hence acts as a catalyst. It also absorbs water to drive the reaction forward.
Why sulphuric acid is added during nitration?
Nitration Reaction
The sulfuric acid is used as dehydration agent and promotes the formation of reactive nitronium ions (Eq. 1). The nitration as addition of the nitronium ion to the aromatic compound occurs in the aqueous acid phase.
Why h2so4 is used in nitration?
Why nitration of chlorobenzene is difficult?
Its rate depends on how electron rich the ring is. (More electron rich rings react faster). Since Chloro is an electron withdrawing substituent, chlorobenzene is less electron rich than benzene. Thus.. the nitration will be slower.
Why is nitration of benzene electrophilic substitution?
Nitration and sulfonation of benzene are two examples of electrophilic aromatic substitution. The nitronium ion (NO2+) and sulfur trioxide (SO3) are the electrophiles and individually react with benzene to give nitrobenzene and benzenesulfonic acid respectively.
Why H2SO4 is used in nitration?
What is nitration explain with example?
Nitration reactions are notably used for the production of explosives, for example the conversion of guanidine to nitroguanidine and the conversion of toluene to trinitrotoluene (TNT). However, they are of wide importance as chemical intermediates and precursors.