Heating of 2-chloro-1-phenylbutane with EtOK/EtOH gives X as the major product. Reaction of X with Hg(OAc)2/H2O…

Step 1: First reaction - E2 elimination

2-chloro-1-phenylbutane + EtOK/EtOH → E2 elimination

Structure: $\ce{Ph-CH2-CHCl-CH2-CH3}$

Zaitsev's rule: More substituted alkene

$\ce{Ph-CH2-CHCl-CH2-CH3 ->[EtOK] Ph-CH2-CH=CH-CH3 + KCl}$

Product X: 1-Phenylbut-2-ene (internal alkene)

Step 2: Second reaction - Oxymercuration-demercuration

Oxymercuration-demercuration:

1. $\ce{Hg(OAc)2/H2O}$ → Adds OH (Markovnikov)
2. $\ce{NaBH4}$ → Removes Hg, replaces with H

Net result: Markovnikov hydration (no rearrangement)

$\ce{Ph-CH2-CH=CH-CH3 ->[Hg(OAc)2/H2O][NaBH4] Ph-CH2-CH(OH)-CH2-CH3}$

Product Y: 2-Phenylbutan-2-ol (OH at more substituted carbon)

Wait, let me reconsider the structure.

Actually, for $\ce{Ph-CH2-CH=CH-CH3}$:

• Markovnikov addition puts OH at C-2 (more substituted)

Product Y: 1-Phenylbutan-2-ol

Structure: $\ce{Ph-CH2-CH(OH)-CH2-CH3}$

Answer: (b)

Key Reactions:

Oxymercuration-demercuration:

• Markovnikov addition of water
• No carbocation rearrangement (unlike acid-catalyzed hydration)
• Syn addition

Mechanism:

1. $\ce{Hg(OAc)2}$ forms mercurinium ion
2. Water attacks more substituted carbon
3. $\ce{NaBH4}$ reduces C-Hg to C-H

Comparison:

• Acid-catalyzed: Markovnikov, rearrangements possible
• Oxymercuration: Markovnikov, no rearrangements
• Hydroboration: Anti-Markovnikov, syn addition