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Why was the iodide ion successful for the SN2 reactions? What if you had used NaF instead of
NaI? Could you use NaBr to react with alkyl chlorides? Could you use NaCl to react with alkyl
bromides?
Solution
Iodide ion is a good nucleophile because the electron on iodine is loosely bounded and I- is less
solvated and hence the size of I- is small in solution. Hence I- is good nucleophile.
Hence the iodide ion successful for the SN2 reactions.
Nucleophilicity order of halide ions
F- < Cl- < Br- < I-
Due to higher electronegativity of F and F- is highly solvated. so size of the solvated ion is large.
so F- is bad nucleophile. Hence SN2 reaction does not occur if we use NaF instead of NaI.
NaBr produce Br- ion which is beter nucleophile in compare to Cl-. so NaBr react with alkyl
chlorides by SN2 mechanism.
NaCl does not react with alkyl bromides because Cl- is bad nucleophile.

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Why was the iodide ion successful for the SN2 reactions What if you.pdf

  • 1. Why was the iodide ion successful for the SN2 reactions? What if you had used NaF instead of NaI? Could you use NaBr to react with alkyl chlorides? Could you use NaCl to react with alkyl bromides? Solution Iodide ion is a good nucleophile because the electron on iodine is loosely bounded and I- is less solvated and hence the size of I- is small in solution. Hence I- is good nucleophile. Hence the iodide ion successful for the SN2 reactions. Nucleophilicity order of halide ions F- < Cl- < Br- < I- Due to higher electronegativity of F and F- is highly solvated. so size of the solvated ion is large. so F- is bad nucleophile. Hence SN2 reaction does not occur if we use NaF instead of NaI. NaBr produce Br- ion which is beter nucleophile in compare to Cl-. so NaBr react with alkyl chlorides by SN2 mechanism. NaCl does not react with alkyl bromides because Cl- is bad nucleophile.