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Synthesis of Diiodomethane by the Finkelstein Reaction

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First published at 17:57 UTC on September 5th, 2020.

#finkelstein
#diiodomethane
#iodine

poormanschemist

PoorMansChemist

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In this video I demonstrate the original Finkelstein Reaction by synthesizing diiodomethane from dichloromethane. The Finkelstein Reaction can be used to convert methyl and primary alkyl chlorides and alkyl bromides to alkyl iodides. The reaction requires nothing more than dry acetone and sodium iodide (potassium iodide will not work). Secondary alkyl chlorides and alkyl bromides will react but the reaction rate is dramatically slower. Tertiary alkyl halides are unreactive. An aromatic Finkelstein reaction also exists as do improved versions of the reaction for aliphatic compounds.

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Notes on the Finkelstein Reaction with protocols and calculations: http://www.poormanschemist.com/PMC_Notebook/August%202020/PMC_LabNotebook_August_2020.html
Wiki Page for the classical Finkelstein Reaction: https://en.wikipedia.org/wiki/Finkelstein_reaction
Organic-Chemistry.org Page for the Finkelstein Reaction (all versions): https://www.organic-chemistry.org/namedreactions/finkelstein-reaction.shtm

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