What does NaI in acetone do?

What does NaI in acetone do?

NaI in acetone is the reagent used in Finkelstien reaction. Alkyl halides are treated with the reagent to give alkyl iodides. The important aspect of this reaction is that the reaction is driven forward because of the lower solubility of the products NaCl and NaBr in acetone even though I- is a weak nucleophile.

What is the nucleophile in the reactions using NaI in acetone?

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).

What is the reaction between alkyl halide and NaI in the presence of acetone?

The classic Finkelstein reaction entails the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone. Sodium iodide is soluble in acetone while sodium chloride and sodium bromide are not.

Why is SN2 favored by NaI in acetone?

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.

Is NaI soluble acetone?

1. Iodide ion is a good nucleophile and sodium iodide is quite soluble 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.

Which compound on reaction is NaI acetone?

meso-2,3-dibromobutane on reaction with NaI/acetone gives trans-2-butene.

What happens when +2 Iodobutane is treated with NaI in acetone?

Therefore, if (R)-2-iodobutane is treated with NaI, repeated SN2 reactions occur. As a result, eventually a racemic mixture of (±)-2-iodobutane is obtained.

Why is NaI soluble in acetone?

Here, Iodine anion is larger in size(ionic radius) than chlorine or bromine anion. This makes NaI attain some covalent properties. Therefore, it easily dissolves with dry acetone( which is an organic solvent and covalent character allows compunds to be soluble in Organic solvents).

What does NaI do in a reaction?

The halogen of the alkyl halide serves as leaving group at the reactive sp3 hybridized carbon. The iodide displaces the halogen leaving group, resulting in a substituted product (alkyl iodide) and a sodium salt (NaBr or NaCl).

What happens when 2-iodobutane is treated with NaI in acetone?

I- is a good nucleophile as well as a good leaving group. Therefore, if (R)-2-iodobutane is treated with NaI, repeated SN2 reactions occur. As a result, eventually a racemic mixture of (±)-2-iodobutane is obtained.

What happens when sodium chloride reacts with acetone?

Since it’s dry acetone, the driving force for the reaction is the precipitation of Sodium Chloride in acetone. By becoming solid, it’s concentration is reduced, Increasing the concentration of reactant pushes the equilibrium to counteract the change in concentration. Why it happens is more important than rr-writing it which is not useful.

Why is Nanai soluble in acetone?

NaI is soluble in acetone. More soluble than NaBr and NaCl is insoluble in acetone. If water got in, it would find and dissolve NaCl. Since it’s dry acetone, the driving force for the reaction is the precipitation of Sodium Chloride in acetone.

What happens when meso-2-3-dibromobutane reacts with Nai/acetone?

But now I came across this: meso-2,3-dibromobutane on reaction with NaI/acetone gives trans -2-butene. d/l-2,3-dibromobutane on reaction with NaI/acetone gives cis -2-butene. I have no problem regarding the first statement.

What is Le Chatelier’s principle in acetone reaction?

Acetone is exactly this type of a reagent. For this case Le Chatelier’s principle means that reaction will be driven to the direction in which one of the reagents gets outside of the solution. Since KCl K C l keeps precipitating the reaction will be driven to the desired product.