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.

Related questions
See all questions in Naming Functional Groups
Impact of this question
60546 views around the world
You can reuse this answer
Creative Commons License