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in arranging the compounds according to increasing order of nucleoplicity if all the compounds have negative charge with lone pair of electrons and if the +m effect is more dominating than -i effect then how will arrange the compounds for example in case of sodium bengote(1),paramethylsodium bengoate(2),para methoxy sodium bengoate(3) and para chloro sodium bengoate(4) . sir in these given compound if we arrange the compounds according to the +m effect the arrangement should according as 3,4,2,1 but scince we have to also take into account the+i effect of the functional group then what should be the increasing order of of there nucleophilicity? and please thhe the short hand method to see which nucleophili is more strong ?

in  arranging the compounds according to increasing order of nucleoplicity if all the compounds have negative charge with lone pair of electrons and if the +m effect  is more dominating than -i effect then how will arrange the compounds for example in case of sodium bengote(1),paramethylsodium bengoate(2),para methoxy sodium bengoate(3) and para chloro sodium bengoate(4) . sir in these given compound if we arrange the compounds according to the +m effect the arrangement should according as 3,4,2,1 but scince we have to also take into account the+i effect of the functional  group then what should be the increasing order of of there nucleophilicity? and please thhe the short hand method to see which nucleophili is more strong ? 

Grade:12

1 Answers

Pankaj
askIITians Faculty 131 Points
6 years ago
All the three groups -Cl, -OCH3and -CH3.
Order of +I effect is
-Cl < -OCH3< -CH3<CH2-CH3
As we know , +I effect or electron releasing effect of any substituent increases the electron density on ring which results in decreasing the nucleophilicity of compounds.
Sodium benzoate does not have electron releasing group while p- methoxy sodium benzoate, p- methylsodium benzoate and p- chlorosodium benzoate have -OCH3, --CH3 and -Cl groups respectively which show +I effect and decrease thenucleophilicity.
So, if we take only +I effect in account the order would be
i.e.Sodium benzoate >p- chloro sodium benzoate >p- methoxy sodium benzoate>p- methyl sodium benzoate

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