What is the mechanism of the reaction of NaI in acetone with an alkyl halide?

1 Answer
anor277
Jan 10, 2016

This operates by the #S_(N)2# mechanism. The iodide ion is a reasonably good nucleophile, and adds as #I^-#

Explanation:

#R-Cl + Na^+I^-# #rarr# #R-I + NaCldarr#

Because sodium iodide is much more soluble than sodium chloride in acetone, when you do this you see a glassy precipitate of sodium chloride in the acetone. I think there is a named organic spot test for this reaction (its name escapes me at the moment, I should not have finished that bottle of wine last night!). If you have time in an organic laboratory it would be worth your while to do this reaction in a small test tube so you can notice the turbidity of the sodium chloride when it precipitates.

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