What does sodium iodide in acetone do?
In the presence of sodium iodide in acetone, alkyl halides that are not sterically hindered (i.e., primary or secodary) react with the iodide nucleophile through an SN2 mechanism. The halogen of the alkyl halide serves as leaving group at the reactive sp3 hybridized carbon.
Does sodium iodide react with acetone?
Sodium iodide is soluble in acetone while sodium chloride and sodium bromide are not. The reaction is driven toward products by mass action due to the precipitation of the poorly soluble NaCl or NaBr.
How does the sodium iodide test work?
A solution of sodium iodide in acetone is a test for some alkyl chlorides and bromides. The mechanism is largely SN2, so primary alkyl halides react faster than secondary alkyl halides, and tertiary alkyl halides generally give no reaction.
Why is sodium iodide in acetone SN2?
For SN2 reactions, NaI in acetone is chosen as iodide ion is a good nucleophile and acetone is a polar aprotic solvent, favoring a SN2 mechanism. The NaBr and NaCl formed in this reaction are insoluble in acetone, so that the time to produce a cloudy solution can be compared as a measure of relative rates.
Is sodium iodide in acetone a strong nucleophile?
To encourage an SN2 reaction mechanism you will use a solution of NaI in acetone. Iodide is a good nucleophile, and if it displaces bromide or chloride, NaBr or NaCl will precipitate (these are much less soluble in acetone than NaI).
Is sodium iodide soluble in acetone?
Iodide ion is a good nucleophile and sodium iodide is quite soluble in acetone. On the other hand, sodium chloride and sodium bromide have low solubilities in acetone. As a result, the reaction of alkyl bromides and alkyl chlorides with NaI/acetone can serve as a simple test reaction as indicated below.
How do you test for Bromobutane?
The silver nitrate test is sensitive enough to detect fairly small concentrations of halide ions. The mixture is acidified by adding dilute nitric acid. This prevents unreacted hydroxide ions reacting with the silver ions to give a confusing precipitate….
| ion present | observation |
|---|---|
| I- | very pale yellow precipitate |
Is sodium iodide a strong or weak nucleophile?
Iodide is a good nucleophile, and if it displaces bromide or chloride, NaBr or NaCl will precipitate (these are much less soluble in acetone than NaI).
What is the solubility of sodium iodide NaI?
Sodium iodide [NaI] SOLUBILITY: 2-butanone [C 4H 8O]: 22,8 (-10°), 15 (20°), 8,9 (50°) amyl alcohol [C 5H 11OH]: 16,3 (25°) ammonia liquid [NH 3]: 131,9 (0°), 146,3 (25°)
How do alkyl halides react with sodium iodide in acetone?
In the presence of sodium iodide in acetone, alkyl halides that are not sterically hindered (i.e., primary or secodary) react with the iodide nucleophile through an SN 2 mechanism. The halogen of the alkyl halide serves as leaving group at the reactive sp 3 hybridized carbon.
What is the molecular weight of sodium iodide?
Sodium iodide PubChem CID 5238 Molecular Weight 149.8942 Component Compounds CID 5360545 (Sodium) CID 24841 (Hydriodi Date s Modify 2021-07-10 Create 2005-03-25
Can acetone be used to solvate sodium halides?
If you go by Henry Rzepa’s blog, the solvation of sodium halides by acetone leads to a solvent shell that isn’t well “fit” for a chloride or bromide anion.
https://www.youtube.com/watch?v=CB81ajz0nj0