See image — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

Concept: The reaction of an alkyl halide with NaI in acetone is the Finkelstein reaction. NaI in acetone selectively replaces the more reactive halide (primary C-X) over a less reactive one (secondary C-X), because NaI is soluble in acetone but NaCl and NaBr are insoluble and precipitate out, driving the equilibrium forward for the more reactive site. Step 1: Identify the structure of 1,4-dichlorohexane. 1,4-dichlorohexane has the structure: Cl-CH2-CH2-CH2-CH(-Cl)-CH2-CH3 - C1: primary carbon bearing Cl - C4: secondary carbon bearing Cl Step 2: Determine selectivity with 1 mole of NaI. With only 1 mole of NaI reacting with 1 mole of the dihalide, only one Cl is replaced. The Finkelstein reaction preferentially substitutes the primary alkyl chloride (C1) because primary substrates undergo SN2 much faster than secondary substrates. Step 3: Apply the reaction. NaI replaces the primary Cl at C1 with I, leaving the secondary Cl at C4 intact. Product: I-CH2-CH2-CH2-CH(-Cl)-CH2-CH3 Step 4: Evaluate the options. (a) Shows Cl at C1 and I at C4 (secondary position replaced) - incorrect, secondary is less reactive in SN2. (b) Shows I at C1 but only a 5-carbon chain with Cl at C3 - incorrect structure/numbering. (c) Shows an elimination product - incorrect, Finkelstein gives substitution not elimination. (d) Shows I at C1 (primary) and Cl at C4 (secondary) on a hexane chain - this is correct. Therefore, the correct answer is D.