Reactivity of Alkyl helides (Application of I Effect)


Application of I-Effect

II. Reactivity of Alkyl halides (based on the stability of carbocation)
Alkyl halides are more reactive than corresponding alkanes.
Methyl chloride is more reactive than methane.

Reason:-
CH3δ+—Clδ-                                                                  CH3—H
-I effect of Cl                                                                   I effect of H is ZERO
Polar bond (Polar compound)                                          Non-polar bond (Non-polar compound)
More reactive                                                                  Less reactive
So, Methyl chloride is more reactive than methane due to –I effect of –Cl


 Special point:-
More stable intermediate or product, more will be formed.
             A <=================> B
             x%                                               y%
If B is more stable than A ==>  y > x
If A is more stable than B ==>  x > y

CH3—CH2—Cl  <=========>  CH3—C+H2  +  Cl-
Reactant-I                                            Intermediate-I
(CH3)3C—Cl     <=========>    (CH3)3C+  +  Cl-
Reactant-II                                          Intermediate-II
(CH3)3C+  is more stable than  CH3—C+H2  So, Intermediate-II is more formed than Intermediate-I and (CH3)3C—Cl  is more reactive than CH3—CH2—Cl 


 Special point:-
Reactivity of reactant is directly proportional to the stability of intermediate.
Reactivity  ∝  Stability of intermediate
*More stable intermediate, more reactive corresponding reactant.

Reactivity order of Alkyl halide [SN1 reaction]
a.      CH3—Cl     b.  CH3—CH2—Cl   c.  (CH3)2C—Cl   d.  (CH3)3C—Cl
Their Carbocation and stability order:-
a.      CH3+       <    b.  CH3—C+H2   <    c.  (CH3)2C+   <    d.  (CH3)3C+
a.      Methyl carbocation  <  b. 1’C  <  c. 2’ C  <  d. 3’C
So reactivity order:-
a.      CH3—Cl    <   b.  CH3—CH2—Cl   <   c.  (CH3)2C—Cl   <   d.  (CH3)3C—Cl


Question:-
Which of the following easily gives white ppt of  AgCl  with silver nitrate?
a.      CH3—Cl     b.  CH3—CH2—Cl   c.  (CH3)2C—Cl   d.  (CH3)3C—Cl
Answer:-  (d)


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