As the unprotonated aniline reacts, it is replenished, by Le Châtelier’s principle. If the opposite is observed, the substituent is called a meta directing group. predict the product or products formed from the reaction of a given monosubstituted benzene derivative with each of the electrophiles discussed in this chapter. Substituents already present on a benzene ring also influences the rate of reaction. 116) The ortho/para product ratio is expected to be the smallest for the bromination of which of these? eg. The aldehyde carbonyl group (and carbonyl groups in general) is a metadirecting substituent.We'll look at the resonance structures of the intermediate for an explanation: Meta Addition of an Electrophile to an Activated Aromatic Ring Mechanistically, the pathways for both ortho and para nitration of acetanilide are essentially equivalent, yet when the reaction is … 115) What is a feature found in all ortho-para directing groups? As is known, these two substituents have completely opposite electronic properties and therefore, opposite effects on the electrophilic substitution reactions of benzene. classify each of the substituents listed in Objective 2 of Section 16.4 as being ortho/para directing activators, ortho/para directing deactivators, or meta directing deactivators.

actually u see though aniline is o,p directing,in the nitration of aniline aniline is always accompanied by oxidation. That is why besides the ortho and para derivatives, significant amount of meta derivative is … Sulphonation Sulphuric acid reacts vigorously with aniline to form anilinium hydrogen sulphate which on heating produces sulphanilic acid which in turn also has a resonating structure with zwitter ion as shown in the above figure. 7 years ago. (v) Aniline does not undergo Friedel-Crafts reaction: A Friedel-Crafts reaction is carried out in the presence of AlCl 3. 0 0 2. 2: Thus, the nitro group is a meta directing group. (b) Nitration: Direct nitration of aniline yields tarry oxidation products in addition to the nitro derivatives. eg. For this reason, aniline on nitration gives a substantial amount of m-nitroaniline. It is likely that the p-nitroaniline product arises by the rapid nitration of the minuscule amount of highly reactive unprotonated aniline in the reaction mixture. In this work, we would like to study the substituent effects of NH 2 and NO 2 groups on benzene using Kohn–Sham density functional theory. The resonance can be shown by depicting the charge as being in the para, ortho, and meta positions. Aniline in presence of strong acids mainly gives the m-substituted product although aniline is o,p-directing in aq. It is because the aniline molecule gets protonated in acidic medium to become anilinium ion which is meta directing. Log in to reply to the answers Post; Anonymous. Sulphonation Sulphuric acid reacts vigorously with aniline to form anilinium hydrogen sulphate which on heating produces sulphanilic acid which in turn also has a resonating structure with zwitter ion as shown in the above figure.

c) The group has the ability to delocalize the positive charge of the arenium ion. In an acidic medium, aniline is protonated to give anilinium ion (which is meta-directing).
Moreover, in the strongly acidic medium, aniline is protonated to form the anilinium ion which is meta directing. nitric acid is a strong acid hence it protonates forming anilinium ion anilinium ion is meta directing because of positive charge on nitrogen ion.hence meta nitro aniline is formed . Because nitro groups are meta-directing, the product will be m-dinitrobenzene. A substituent group is either an ortho, para-directing group or a meta-directing group in all electrophilic aromatic substitution reactions; that is, no substituent is ortho, para directing in one reaction and meta directing in another.


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