Question

In: Chemistry

Rank the following functionalities from worst to best leaving group ability. Which favor an Sn1 mechanism...

Rank the following functionalities from worst to best leaving group ability. Which favor an Sn1 mechanism and why?

F-, OH-,OTs-,Br-,H2O

Solutions

Expert Solution

The order worst to best leaving group is

OH- < F- < Br-< H2O < OTs-

The leaving group ability mainly depends on two factors

1) strength of C - X (X: leaving group) bond

and

2) Polarization of C-X bond

Or we can say

A good leaving group is a bulkier weak base/acid.

OTs- is a weak conjugate base of TsOH strong acid since it is a bulkier base, its overlap is weakest with C.

H2O is a weak conjugate acid of strong base OH- ion so H2O is a good leaving group.

Due to the protonation of OH with H+ ions, H2O is formed. C-O overlap will decrease and H2O becomes good leaving group.

Br- is weak conjugate base of strong acid HBr

F- and OH- have the same size but F- is more electronegative than O so OH is worst leaving group than F


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