Join WhatsApp Icon JEE WhatsApp Group
Question 45

For the reaction

image


The correct statement is

The given reaction is the Finkelstein reaction, which proceeds through an $$S_N2$$ (bimolecular nucleophilic substitution) mechanism.

In this reaction, an alkyl bromide ($RCH_2Br$) reacts with an iodide ion ($I^-$) in the presence of acetone to form an alkyl iodide ($RCH_2I$).

Consider each statement individually.

For option (C):

Initially, the reactants consist of a neutral alkyl halide and a localized iodide ion ($I^-$), where the entire negative charge resides on a single iodine atom.

During the $$S_N2$$ reaction, the nucleophile attacks the carbon atom while the leaving group departs simultaneously, producing the transition state

$$[I^{\delta-}\cdots CH_2(R)\cdots Br^{\delta-}]^{\ddagger}.$$

In this transition state, the negative charge is distributed over the incoming iodine atom, the central carbon atom, and the leaving bromine atom rather than being localized on a single atom.

As a result, the transition state has a lower charge density and is therefore less polar than the isolated iodide ion.

Hence, statement (C) is correct.

For option (A):

In the Finkelstein reaction, acetone dissolves sodium iodide but not sodium bromide.

As the reaction proceeds,

$$NaBr$$

precipitates out of the solution, removing $$Br^-$$ ions from the reaction mixture.

Therefore, $$Br^-$$ cannot effectively act as a competing nucleophile.

Hence, statement (A) is incorrect.

For option (B):

Acetic acid is a polar protic solvent.

Polar protic solvents strongly solvate nucleophilic anions such as $$I^-$$ through hydrogen bonding, significantly reducing their nucleophilicity and slowing the $$S_N2$$ reaction.

The Finkelstein reaction requires a polar aprotic solvent such as acetone.

Hence, statement (B) is incorrect.

For option (D):

Acetone is a polar aprotic solvent and does not strongly solvate anions because it cannot form hydrogen bonds with them.

Moreover, the rate-determining step involves a transition state rather than freely solvated ions.

Therefore, the statement that the solvent solvates the ions formed in the rate-determining step is incorrect.

Hence, statement (D) is incorrect.

Therefore, the only correct statement is

(C) The transition state is less polar than the iodide ion.

Get AI Help

Video Solution

video

Create a FREE account and get:

  • Free JEE Mains Previous Papers PDF
  • Take JEE Mains paper tests

JEE Quant Questions | JEE Quantitative Ability

JEE DILR Questions | LRDI Questions For JEE

JEE Verbal Ability Questions | VARC Questions For JEE

Free JEE Topicwise Questions

JEE Rotational MotionJEE Units & MeasurementsJEE Atomic StructureJEE GravitationJEE Periodic Table & PeriodicityJEE StatisticsJEE Inverse Trigonometric FunctionsJEE Magnetism & Magnetic MaterialsJEE Sequences & SeriesJEE MatricesJEE Alternating CurrentsJEE Carboxylic AcidsJEE Permutations & CombinationsJEE Work, Energy & PowerJEE Electromagnetic InductionJEE Electronic DevicesJEE d and f-Block ElementsJEE Chemical KineticsJEE Heat TransferJEE Three Dimensional GeometryJEE Magnetic Effects of CurrentJEE Hydrocarbons - AromaticJEE Electromagnetic WavesJEE Aldehydes & KetonesJEE Hydrocarbons - AlkanesJEE Applications of DerivativesJEE EquilibriumJEE Indefinite IntegrationJEE Chemical ThermodynamicsJEE ElectrochemistryJEE ProbabilityJEE BiomoleculesJEE Continuity & DifferentiabilityJEE Kinetic Theory of GasesJEE Vector AlgebraJEE Hydrocarbons - AlkynesJEE Differential EquationsJEE Current & ResistanceJEE Straight LinesJEE WavesJEE Redox ReactionsJEE Hydrocarbons - AlkenesJEE DeterminantsJEE SolutionsJEE Ray OpticsJEE Dual Nature of Matter & RadiationJEE Chemical Bonding & Molecular StructureJEE Complex NumbersJEE Sets, Relations & FunctionsJEE Electric Charges & FieldsJEE Laws of MotionJEE Fluid MechanicsJEE Basic Concepts in ChemistryJEE Trigonometric FunctionsJEE LimitsJEE Laws of ThermodynamicsJEE Kinematics - 2D MotionJEE p-Block Elements (Groups 13-18)JEE Simple Harmonic MotionJEE Electric Potential & CapacitanceJEE Coordination CompoundsJEE JEE 2D GeometryJEE CirclesJEE Definite IntegrationJEE EMF & Circuit AnalysisJEE Surface TensionJEE Atoms & NucleiJEE Laboratory Experiments - XIJEE Number SystemJEE Basic Principles of Organic ChemistryJEE Wave OpticsJEE Quadratic EquationsJEE Alcohols, Phenols & EthersJEE Organic Compounds with HalogensJEE DifferentiationJEE Conic SectionsJEE Nitrogen-Containing CompoundsJEE ElasticityJEE Practical Organic ChemistryJEE Kinematics - 1D MotionJEE Purification & CharacterisationJEE Binomial Theorem
Ask AI