Organic Chemistry Practice Problems Leaving Groups Practice Problems Solution: Rank the following in decreasing order of leaving ...

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Solution: Rank the following in decreasing order of leaving group ability.a) I > III > IV > IIb) I > III > II > IVc) III > II > I > IVd) II > I > III > IV

Problem

Rank the following in decreasing order of leaving group ability.

a) I > III > IV > II

b) I > III > II > IV

c) III > II > I > IV

d) II > I > III > IV

Solution

We’re being asked to rank the given leaving groups in decreasing order of leaving group ability.



Recall that leaving group ability depends on the stability of a leaving group after gaining a negative charge. This means the factors affecting acidity can be applied as well to leaving groups.


Also, recall that the good leaving groups discussed previously are:

1. Halides

2. Sulfonate Esters

3. Water


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