tags
diethyliodidesodiumethylnitroethaneethyl iodideetherNitroethanesilverethanol

video tutorial Nitroethane from ethyl iodide and silver nitrite ('Victor Meyer reaction')

Nitroethane synthesis summary
  • Two-part process: prepare dry silver nitrite; react with ethyl iodide in diethyl ether to form nitroethane.
  • Silver nitrite preparation: weigh 42 g silver nitrate, dissolve in 100 mL water; weigh 19 g sodium nitrite, dissolve in 100 mL water; combine to form a yellow precipitate (silver nitrite); stir 15 minutes; filter and dry; wash with 40 mL cold water; dry again; add 40 mL absolute ethanol; stir to absorb water; filter off ethanol and dry again; repeat ethanol wash; dry the solid; store in a desiccator; wrap if light sensitive; after a week the solid is dry; weigh about 35 g.
  • Reaction setup: in a 500 mL flask, place silver nitrite in cold water; measure 60 mL diethyl ether; add to the flask; in the addition funnel place 33.7 g ethyl iodide (based on moles of silver nitrate); add 30 mL more diethyl ether; keep addition funnel closed; use an ice bath at 0°C with thermometer, addition funnel, and reflux condenser as precautions.
  • Perform addition slowly over ~45 minutes while stirring; aim to keep the mixture at 8–12°C during addition; after addition, keep stirring on the ice bath for 1 hour, then continue stirring at room temperature for about 4 more hours; monitor reaction by sampling a drop of reaction liquid—milky color indicates incomplete reaction; continue until no milkiness is observed (about 7 hours total).
  • Workup: filter the reaction mixture, wash the solids with two portions of 50 mL diethyl ether; process the filtrate by distilling off ether to recover the solvent; isolate 10–15 mL pale yellow liquid; set up distillation to remove residual ether carefully; distill slowly to around 130°C to obtain colorless nitroethane; total distillation time about 1 hour.
  • Yield: 9.2 g nitroethane (57% yield based on ethyl iodide used); literature reports 50–80% yields; nitroethane is an important synthetic building block; method requires ether and silver salts.

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