How can we apply Ortho effect to check the acidic character in aromatic compounds?

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How can we apply Ortho effect to check the acidic character in aromatic compounds?

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How can we apply Ortho effect to check the acidic character in aromati...

The ortho effect if based on the premise that an ortho-substituted acid (take benzoic acid as an example) is more acidic than the meta or para-substituted form. This effect is not dependent on the nature of the substituent (e- donating or e- withdrawing). The reason for this is that the steric hinderance between the substituent and the neighboring carboxylate forces the carboxylate to bend out of the plane of the aromatic ring. This conformational shift alters the delocalization of the charge into the benzene ring, making it easier for the negative charge to be delocalized throughout the pi-system.

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Can you explain the answer of this question below:On the basis of aromaticity, there are three types of compounds i.e. aromatic, non-aromatic and antiaromatic.The increasing order of stability of these compounds are is under:Anti-aromatic compound non-aromatic compound aromatic compounds. Compounds to be aromaticfollow the following conditions (according to valence bond theory)(i) The compounds must be be cyclic in structure having (4n + 2) e, where n = Hckels number = 0, 1,2, 3 et.c(ii) The each atoms of the cyclic structure must have unhybridised p-orbital i.e. the atoms of thecompounds have unhybridised p-orbital i.e. usually have sp2 hybrid or planar.(iii) There must be a ring current of electrons in the ring or cyclic structure i.e. cyclic structure mustundergo resonance .Compounds to be anti-aromatic, it must have 4ne where n = 1, 2 and it must be planar and undergoresonance. Non-aromatic compounds the name itself spells that compounds must be non-planarirrespective of number of electrons. Either it has 4ne or (4n + 2) electrons it does not matter.The rate of reaction of any aromatic compounds depends upon the following factors:(i) Electron density(ii) stability of carbocation producedHigher the amount of electron density of the ring, higher will be its rate towards aromatic electrophilicsubstitution and vice-versa. Similarly, higher will be the stability of the produced carbocation after theattack of electrophile, higher will be its rate towards aromatic electrophilic substitution. There is a greateffect of kinetic labelling on the rate of aromatic electrophilic substitution. As we known that higher theatomic weight or, molecualr weight, higher will be the van der Waals force of attraction or, bond energy.Since there will be effect of kienetic labelling if the 2nd step of the reaction will be the slow step, (r.d.s.)otherwise there will be no effect of kinetic labelling.Q. Which of the following is correct order of the rate of reaction of C6H6, C6D6 and C6T6 towardsnitrations?A:C6H6 C6D6 C6T6B:C6H6 = C6D6 = C6T6C:C6H6 C6D6 = C6T6D:C6T6 C6D6 C6H6The answer is b.

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On the basis of aromaticity, there are three types of compounds i.e. aromatic, non-aromatic and antiaromatic. The increasing order of stability of these compounds are is under: Anti-aromatic compound < non-aromatic compound < aromatic compounds. Compounds to be aromaticfollow the following conditions (according to valence bond theory)(i) The compounds must be be cyclic in structure having (4n + 2)π e–, where n = Hückel’s number = 0, 1, 2, 3 et.c(ii) The each atoms of the cyclic structure must have unhybridised p-orbital i.e. the atoms of the compounds have unhybridised p-orbital i.e. usually have sp2 hybrid or planar.(iii) There must be a ring current of π electrons in the ring or cyclic structure i.e. cyclic structure mustundergo resonance .Compounds to be anti-aromatic, it must have 4nπe– where n = 1, 2… and it must be planar and undergo resonance. Non-aromatic compounds the name itself spells that compounds must be non-planarirrespective of number of π electrons. Either it has 4nπe– or (4n + 2) π electrons it does not matter.The rate of reaction of any aromatic compounds depends upon the following factors:(i) Electron density(ii) stability of carbocation producedHigher the amount of electron density of the ring, higher will be its rate towards aromatic electrophilic substitution and vice-versa. Similarly, higher will be the stability of the produced carbocation after the attack of electrophile, higher will be its rate towards aromatic electrophilic substitution. There is a great effect of kinetic labelling on the rate of aromatic electrophilic substitution. As we known that higher the atomic weight or, molecualr weight, higher will be the van der Waal’s force of attraction or, bond energy. Since there will be effect of kienetic labelling if the 2nd step of the reaction will be the slow step, (r.d.s.) otherwise there will be no effect of kinetic labelling.Q. Which of the following is correct order of the rate of reaction of C6H6, C6D6 and C6T6 towardssulphonation?

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Ortho effect is a special type of effect that is shown by o-substituents, but it is not necessarily just a steric effect. This ortho-effect operates with the benzoic acids. Irrespective of the polar type nearly all o-substituted benzoic acid are stronger than unsubstituted benzoic acid. Benzoic acid is a resonance hybrid and so the carboxyl group is coplanar with the ring. An o-substitueut tends to prevent this coplanarity. Ortho effect also operates in substituted anilines where as ortho substituent has base weakening effect.Q.What is the acidity order of the following compounds ?

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With respect to the compounds I-V, choose the correct statement(s).

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Ortho effect is a special type of effect that is shown by o-substituents, but it is not necessarily just a steric effect. This ortho-effect operates with the benzoic acids. Irrespective of the polar type nearly all o-substituted benzoic acid are stronger than unsubstituted benzoic acid. Benzoic acid is a resonance hybrid and so the carboxyl group is coplanar with the ring. An o-substitueut tends to prevent this coplanarity. Ortho effect also operates in substituted anilines where as ortho substituent has base weakening effect.Q.What is the order of acidity of following compounds

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How can we apply Ortho effect to check the acidic character in aromatic compounds?

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