Vicinal dibromides do not form diols via hydrolysis with water alone

Steps:

• 2,3-Dibromohexane has adjacent Br groups on secondary carbons, allowing SN1/SN2 substitution with water.
• Partial hydrolysis replaces one Br with OH, yielding constitutional isomers A (OH at C2) and B (OH at C3) as bromohydrins.
• The intermediate bromohydrin has adjacent OH and Br, which under hydrolysis conditions favors epoxide formation over second substitution.
• Thus, complete hydrolysis does not produce the vicinal diol; products are only bromohydrins A and B.

Why C is correct:

• Vicinal diols require base-catalyzed epoxide opening or Ag2O(aq); neutral water halts at bromohydrin stage per standard organic mechanisms.

Why the others are wrong:

• A: Forms via partial hydrolysis substituting Br at C2.
• B: Forms via partial hydrolysis substituting Br at C3.
• D: Starting material remains if reaction incomplete, present in mixture.

Final answer: C