Question
Asked Dec 24, 2019
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Rank the species in each group in order of increasing leaving group ability.
a. Br-, Cl-, I-
b. NH3, H2S, H2O

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Expert Answer

Step 1

A leaving group can be defined as a molecular fragment which departs with a pair of electrons in a heterolytic cleavage of bond. A given leaving group can be a neutral molecule or anions as well, but in each of these cases, the leaving group should be able to stabilize the extra electron density which is a consequence of the heterolysis of bond.

Step 2
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A good leaving group is a weak base which means that it will have a strong conjugate acid which will have lower pKa values. The weaker the given base is, better will be the leaving group.

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Step 3
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The given ions are Br, Cl and I. The conjugate acids of each of these are HBr, HCl and HI. The order of the acidity is as follows: HCI<HBr<HI The strength of conjugate base is as follows: Cl>Br>I° The strength of leaving group is as follows: Cl<Br <I

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