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Applications of Inductive effect

         (i) Magnitude of negative and positive charges : Magnitude  of +ve  charge  on cations  and magnitude of -ve charge on anions can be compared by + I or - I groups present in it.

         · Magnitude of +ve charge 624_applications of inductive effect.pngpower of the group.

         · Magnitude of -ve charge 1688_applications of inductive effect1.png  power of the group.

         (ii) Reactivity of alkyl halide : + I effect of methyl group enhances - I effect of the halogen atom by repelling the electron towards tertiary carbon atom.

1041_applications of inductive effect2.png

         Tertiary    >    Secondary   >   Primary  >  Methyl

         (iii) Relative strength of the acids :

         (a) Any group or atom showing +I effect decreases the acid strength as it increases the negative charge on the carboxylate ion which holds the hydrogen firmly. Alkyl groups have + I effect.

Thus, acidic nature is,

2410_applications of inductive effect3.png

     +I effect increases, so acid strength decreases

         Formic acid, obtain no alkyl set, is the most acidic among these acids.

         (b) The group or atom having - I effect increases the acid strength as it decreases the negative charge on the carboxylate ion. Greater is the number of such molecules or sets (having - I effect), greater is the acid strength.

         Thus, acidic nature is,

2285_applications of inductive effect4.png

  (- Inductive effect added, so acid power increases)

            (c) Strength of benzoic acids and aliphatic carboxylic acid

1072_applications of inductive effect5.png

         Hence benzoic acid is stronger acid than aliphatic carboxylic acids but exception is formic acid. So,

             1407_applications of inductive effect6.png

                         Acid strength in decreasing order

  •         Decreasing order of acids :

827_applications of inductive effect7.png

         As compared to water, phenol is more acidic (-I effect) but methyl alcohol is less acidic (+I effect).

        1407_applications of inductive effect8.png

         (vi) Relative strength of the bases (Basic nature of -NH2)

         The difference in base strength in various amines can be explained on the basis of inductive effect. The +I effect increases the electron density while -I effect decreases it. The amines are stronger bases than NH3 as the alkyl groups increase electron density on nitrogen due to + I effect while CINH2 is less basic due to -I effect. "So more is the tendency to donate electron pair for manage with proton, the more is basic function, i.e., more is the negative charge on nitrogen molecule (due to +I effect of alkyl group), the more is base nature".

         Thus, the basic nature decreases in the order;

376_applications of inductive effect9.png

         The order of basicity is as shown in table;

Alkyl groups (R-        )

Relative base strength

CH3

R2NH > RNH2 > R3N > NH3

C2H5

R2NH > RNH2 > NH3 > R3N

(CH3)2CH

RNH2 > NH3 > R2NH > R3N

(CH3)3C

NH3 > RNH2 > R2NH > R3N

  • The relative basic character of amines is not in total accordance with inductive effect (t > s > p) but it is in the following order: Secondary > Primary > Tertiary. The reason is the steric hindrance existing in the t-amines.
  • In gas phase or in aqueous solvents such as chlorobenzene etc, the solvation effect, i.e., the organization of the conjugate acid due to H-bonding are absent and hence in these media the basicity of amines depends only on the +I effect of the alkyl group thus the basicity of amines follows the order : 30 > 20 > 10 > NH3.

         (vii) Basicity of alcohols : The decreasing order of base strength in alcohols is due to +I effect of alkyl groups.

1302_applications of inductive effect10.png

         (viii) Stability of carbonium ion :+I effect tends to decrease the (+ve) charge and -I effect tends to increases the +ve charge on carbocation.

1541_applications of inductive effect11.png

(ix) Stability of carbanion : Stability of carbanion increases with increasing - I effect.

1441_applications of inductive effect12.png

 

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