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Question 54

The major product of the following reaction is:

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  1. Step 1: Base-Mediated Dehydrohalogenation ($$\alpha,\beta$$-Elimination)

    The reaction begins with the elimination of hydrogen bromide ($$-\text{HBr}$$) from the cyclic bromo-ketone precursor. A base abstracts a proton from the $$\beta$$-position relative to the leaving group ($$\text{--Br}$$), triggering an $$\alpha,\beta$$-elimination that forms a stable, conjugated diene intermediate (a cyclohexadienone derivative):

    $$\text{Bromo-ketone Precursor} \xrightarrow{-\text{HBr}} \text{Cyclohexadienone Intermediate [Conjugated diene, stable]}$$

  2. Step 2: Tautomerization (Enolisation to Attain Aromaticity)

    The non-aromatic cyclohexadienone intermediate contains a highly acidic sp3 hybridized carbon bearing two hydrogen atoms adjacent to the carbonyl group ($$\text{C=O}$$). To relieve ring strain and gain immense thermodynamic stability, the compound undergoes rapid enolisation (keto-enol tautomerization). This restores the fully delocalized $$\pi$$-system of the benzene ring:

    $$\text{Cyclohexadienone (Keto form)} \rightleftharpoons \text{Phenol Derivative (Enol form) [Very stable, aromatic]}$$

Conclusion:

The driving force of the entire transformation is the immense resonance energy gained through aromatization, shifting the equilibrium completely toward the formation of the phenol derivative.

Answer: The option displaying the fully aromatic phenol derivative as the major product (Option B).

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