Hydrolysis of alkyl halides proceeds via nucleophilic substitution

Steps:

• Recognize 2-bromopropane as a secondary alkyl halide with formula CH3CHBrCH3.
• Hydrolysis involves reaction with water or aqueous NaOH, replacing Br with OH.
• The OH- ion acts as a nucleophile, attacking the carbon bonded to Br.
• Br- departs as the leaving group, confirming substitution at the carbon center.

Why D is correct:

• Nucleophilic substitution is defined as a nucleophile displacing a leaving group in SN1 or SN2 mechanisms; for 2-bromopropane, secondary nature favors SN1 in polar protic solvents like water.

Why the others are wrong:

• A: Free radical substitution involves radical intermediates from homolytic cleavage, typically in halogenation of alkanes under UV light, not aqueous hydrolysis.
• B: Nucleophilic addition targets electron-deficient multiple bonds in alkenes or carbonyls, absent in saturated 2-bromopropane.
• C: Electrophilic addition occurs when electrophiles add across pi bonds in alkenes, not applicable to the saturated alkyl halide.

Final answer: D