Activation

Increasing the leaving group ability of a leaving group by modifying it chemically is called activation.  Empirically, the leaving group ability of a leaving group is a function of its base strength.  The lower the base strength of a leaving group, the greater its leaving group ability.

eg:


Br ¯  is a weaker base and, therefore, a better leaving group than Cl¯.

To activate a leaving group, the compound carrying it is subjected to a reaction that converts the leaving group into one that is less basic.

eg:



Alcohol 1 can be converted to alkyl halide 2 by treating it with HCl.



The net reaction is nucleophilic substitution:



However, when 1 is treated with Cl¯, no reaction occurs even at high temperature.



The reason is OH¯ is a weak leaving group.

The reaction of 1 with HCl occurs in two stages.

Stage 1:  Activation


The acid-base reaction converts 1 into an oxonium ion (3).

Stage 2:  Nucleophilic Substitution



Water is a much better leaving group than OH¯.  Consequently, 3 in which the leaving group is water undergoes nucleophilic substitution with Cl¯, whereas 1 in which the leaving group is OH¯ does not.

 

 

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