SN2 Reaction: Predicting Reactivity of Five Compounds

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SUMMARY

The discussion centers on predicting the reactivity of five compounds in an SN2 reaction mechanism. Participants concluded that while chloride (Cl) is more electronegative than iodide (I), iodide is a superior leaving group, leading to the correct answer being compound E. The ranking of leaving groups indicates that the primary halide in compound D is less reactive than the iodide in compound E, despite the tertiary nature of compound B. Understanding the hierarchy of leaving groups is crucial for predicting SN2 reactivity.

PREREQUISITES
  • Understanding of SN2 reaction mechanisms
  • Knowledge of leaving group ability, specifically halides
  • Familiarity with the concept of electronegativity
  • Ability to rank reactivity of homologous halides
NEXT STEPS
  • Study the differences in leaving group ability among halides
  • Research the factors influencing SN2 reaction rates
  • Learn about the impact of steric hindrance on SN2 reactions
  • Explore the concept of nucleophilicity in relation to leaving groups
USEFUL FOR

Chemistry students, organic chemists, and anyone interested in understanding reaction mechanisms and predicting compound reactivity in SN2 reactions.

leopard
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Which of these five compounds will react easier after an SN2 mechanism?

Since Cl is more electronegative than I, it is a better leaving group, so I would expect the answer to be B or D.

In B the halide is tertiary while in D it is primary, so I expect D to be the answer.

The correct answer is E. Why?
 
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Because iodide is a better leaving group than chloride. You should have a ranking of rates of reactions for homologous halides in the chapter somewhere.
 

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