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 S_n1 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

queen_honey_blossom answered 1 year ago

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