Question:

CH3CH2-Br \(\overrightarrow{Acetone}^{NaI}\) CH3-CH2-I+NaBr
Which of the following statement is correct ? 

Updated On: Mar 21, 2025
  • Acetic acid solvent can take in above reaction. 

  • NaI is soluble in acetone but NaBr is precipitate in acetone

  • NaI is precipitated in acetone but NaBr is soluble in acetone 

  • When acetone is taken in solvent transition state is highly polar

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The Correct Option is B

Solution and Explanation

CH3CH2-Br + NaI (in acetone) → CH3-CH2-I + NaBr 

Correct Statement:

NaI is soluble in acetone, but NaBr precipitates in acetone.

Explanation:

  • The reaction occurs via the Finkelstein reaction, which is used to prepare alkyl iodides from alkyl bromides or chlorides.
  • Acetone is a polar aprotic solvent that helps dissolve NaI and facilitates the reaction.
  • When NaI reacts with CH3CH2-Br:
    • NaI is soluble in acetone.
    • NaBr, the byproduct, is not soluble in acetone and precipitates out.
  • The precipitation of NaBr drives the equilibrium of the reaction toward the formation of the product, CH3-CH2-I.

Conclusion:

The correct statement is: NaI is soluble in acetone, but NaBr precipitates in acetone.

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Concepts Used:

Haloalkanes and Haloarenes

The hydrocarbons such as Haloalkanes and Haloarenes are the ones, in which one or more hydrogen atoms are replaced with halogen atoms. The main difference between Haloalkanes and Haloarenes is that Haloalkanes are derived from open chained hydrocarbons, also called alkanes, and Haloarenes are derived from aromatic hydrocarbons.

  • Haloalkanes have hydrocarbons made up of aliphatic alkanes and one or more hydrogen atoms replaced by halogens (elements such as Chlorine, Bromine, Fluorine, Iodine, etc.) whereas, haloarenes consist of aromatic ring or rings and one or more hydrogen atoms replaced by halogens.
  • In haloalkanes, the halogen atom is attached to the sp3 hybridized carbon atom of the alkyl group whereas, in haloarenes, the halogen atom is attached to the sp3 hybridized carbon atom of the alkyl group.
  • Haloalkanes are saturated organic compounds where all the chemical bonds are attached to the carbon atom with single bonds and a single carbon atom is attached to the Halogen atom, whereas, the haloarenes differ from Haloalkanes by their method of preparation and properties.
  • Haloalkanes are made by aliphatic alkanes by the process of free radical halogenation, whereas, haloarenes are made by direct halogenation of aromatic rings.
  • Haloalkanes are odorless compounds, whereas, haloarenes have a sweet odor.
  • Haloalkanes precipitate in SN2 substitution reactions, whereas, haloarenes do not precipitate in SN2 substitution reactions.
  • Example of haloalkanes is CH3Cl (Methyl Chloride) and CH3CH2Br (Ethyl Bromide) and the example of haloarenes is Chlorobenzene, Bromobenzene.