Why Does C6H5CH(Cl)CH3 < (CH3)3 CCl < C6H5C(CH3)2 Cl Undergo SN1 Reaction?

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SUMMARY

The discussion centers on the reactivity of three organic compounds in SN1 reactions, specifically the order C6H5CH(Cl)CH3 < (CH3)3CCl < C6H5C(CH3)2Cl. The compound (CH3)3CCl is identified as the most reactive due to the stabilization of the carbocation formed by three electron-donating methyl groups. In contrast, the phenyl group in C6H5CH(Cl)CH3 and C6H5C(CH3)2Cl acts as an electron-withdrawing group, increasing the positive charge on the carbocation and reducing its stability.

PREREQUISITES
  • Understanding of SN1 reaction mechanisms
  • Knowledge of carbocation stability and factors affecting it
  • Familiarity with inductive effects of functional groups
  • Basic organic chemistry nomenclature and structure
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  • Learn about carbocation stability and the role of electron-donating and electron-withdrawing groups
  • Research the effects of resonance and inductive effects on reaction rates
  • Explore examples of SN1 reactions with different alkyl halides
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Organic chemistry students, educators, and anyone interested in understanding reaction mechanisms and the influence of molecular structure on reactivity.

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Homework Statement


i was told that the the ascending order of the compound undergo SN1 reaction is C6H5CH(Cl)CH3 < (CH3)3 CCl < C6H5C(CH3)2 Cl... it's a past year question . I am sure tha ans is correct. Can someone explain why? Generally , the most reactive is the compound (CH3)3 CCl , Am i right? this is because the (CH3)3 C+ is surrounded by three electron donating group , so it stabilise the carbonium ion formed.btw , the phenyl is an electron withdawing group , it draw the elctrons away form the C atoms , making the partial positive charge of the carboium ion formed more higher...

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i was told that the phenyl exerts positive inductive effect? why the phenyl isn't exerts negative inductive effect?
 

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