Question:hard

Identify the major product ‘Q’ in the following reaction:

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Vicinal dibromides with strong base and subsequent hydrolysis give ketones via E2 and hydrolysis of the intermediate.
Updated On: Jul 18, 2026
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The Correct Option is B

Solution and Explanation

Step 1: Recognise this as a standard three-reagent conversion taught as a named sequence.
A vicinal dibromide taken through hot alcoholic KOH, then $NaNH_2$ in liquid ammonia, then dilute aqueous acid is a classic route from a dihalide all the way to a methyl ketone, and each reagent plays one specific, well-known role.

Step 2: First reagent, hot alcoholic KOH: double dehydrohalogenation.
Alcoholic KOH under heat does not stop at removing one HBr. With a vicinal dibromide and forcing conditions, it removes two molecules of HBr in succession, taking the compound all the way from a dibromide to an alkyne, not just an alkene.

Step 3: Second reagent, $NaNH_2$ in liquid $NH_3$ at 195 K: the acetylenic zipper.
Sodamide is a very strong, small base. On an internal alkyne it repeatedly deprotonates and reprotonates along the chain, walking the triple bond down to the end of the chain until it reaches the more stable terminal position. This step converts an internal alkyne into a terminal alkyne.

Step 4: Third reagent, dilute $H_2SO_4$: Markovnikov hydration.
Aqueous acid adds water across the terminal triple bond following Markovnikov's rule, so the $OH$ group lands on the more substituted carbon. The resulting unstable enol immediately tautomerises to the more stable keto form.

Step 5: Identify the final product.
Applying Markovnikov addition to a terminal alkyne derived from a phenyl-substituted chain places the oxygen next to the ring, giving the methyl ketone $C_6H_5COCH_3$, acetophenone, rather than an aldehyde.

Step 6: Rule out the other options.
An aldehyde would need anti-Markovnikov addition, which dilute acid does not give. The starting benzylic bromide and the para-substituted aldehyde do not fit this reagent sequence at all.

Final Answer:
\[ \boxed{C_6H_5COCH_3 \, (\text{Acetophenone})} \]
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