SN2 Reaction: Predicting Reactivity of Five Compounds

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In an SN2 reaction, the reactivity of compounds is influenced by the leaving group ability, where iodide is a superior leaving group compared to chloride. Although Cl is more electronegative, the better leaving group in this context is I, leading to the conclusion that compound E reacts more easily. The discussion also highlights that while compound B has a tertiary halide and compound D has a primary halide, the primary halide in D does not outweigh the leaving group ability of iodide in E. Therefore, despite initial expectations, E is identified as the most reactive compound in the SN2 mechanism. Understanding the hierarchy of leaving groups is crucial for predicting reactivity in these reactions.
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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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