ar Vollharnit and Neil Schore Rank primary, secondary, tertiary, and primary all

Question

ar Vollharnit and Neil Schore Rank primary, secondary, tertiary, and primary allylic chlorides in substitution reactions from most reactive to least reactive. The symbol means the rates are about equivalent a. In SN1 reactions O Tertiary secondary -allyic ho pimary O Primary -secondary tertiary -allylic C Allylic > tertiary h secondary + primary O Tertiary secondany a allylicprimary b. In SN2 reactions O Allylic > primary secondary a tertiary O Primary - allylic > secondary tertiary O Primary > allylic secondary tertiary O Tertiary secondary s primaryallylic

Explanation / Answer

a) 1

SN1. Carbocations stability= Tertiary > Secondary ~Allylic >> Primary

As the first step of the SN1 reaction is loss of a leaving group to give a carbocation, the rate of the reaction will be proportional to the stability of the carbocation. Carbocation stability increases with increasing substitution of the carbon (tertiary > secondary >> primary) as well as with resonance.

b) 1

Allylic>Primary> Secondary >> Tertiary.

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