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Q6.14(iii):

Write the structure of the major organic product in each of the following reactions: 

Solution :

Step 1: Analyzing the Substrate and Reagent

The substrate is 1-bromo-methylcyclohexane (or bromomethylcyclohexane). The reactant provided is $NaI$ (Sodium Iodide) in the presence of acetone. This reaction system is characteristic of the Finkelstein Reaction. [Per the mechanism of nucleophilic substitution, the Finkelstein reaction is a specific application of the $S_N2$ mechanism used for the preparation of alkyl iodides from alkyl chlorides or bromides].

Step 2: Mechanism of the Reaction

The reaction follows an $S_N2$ (Substitution Nucleophilic Bimolecular) pathway.

  • Nucleophile: The Iodide ion ($I^-$) acts as a strong nucleophile.
  • Leaving Group: The Bromide ion ($Br^-$) is a good leaving group.
  • Solvent: Acetone is a polar aprotic solvent. It facilitates the $S_N2$ mechanism by not solvating the nucleophile strongly, thereby increasing its nucleophilicity. Additionally, $NaBr$ is insoluble in acetone and precipitates out of the solution, which drives the reaction to completion according to Le Chatelier’s Principle.

Step 3: Structural Transformation

The iodide ion attacks the primary carbon atom attached to the bromine from the backside, resulting in the displacement of the bromide ion. The cyclohexane ring remains intact as a spectator group.

Reaction Equation:

$C_6H_{11}CH_2Br + NaI \xrightarrow{\text{acetone}} C_6H_{11}CH_2I + NaBr \downarrow$

Step 4: Visualization of the Molecular Structure

C6H11 CH2I Major Product: (Iodomethyl)cyclohexane

Step 5: Analytical Summary

The reaction is a clean substitution at the primary carbon. There is no possibility of rearrangement as the nucleophile attacks directly at the carbon bearing the leaving group. The formation of the $NaBr$ precipitate effectively shifts the chemical equilibrium toward the formation of the alkyl iodide.

Final Solution: The major organic product is (Iodomethyl)cyclohexane, with the structural formula $C_6H_{11}CH_2I$.


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