See image — Aromatic Hydrocarbons Chemistry Question

💡 Solution & Explanation

Step 1 - Identify the structure of phenyl benzoate. Phenyl benzoate is C6H5-COO-C6H5. It has two rings: the acyl (benzoyl) ring bearing the -COO- group as a substituent, and the phenoxy ring bearing the -OOC- group as a substituent. Step 2 - Determine directing effects on each ring. - Acyl (benzoyl) ring: The -COO- group acts as an electron-withdrawing group (meta director) through resonance and induction. Therefore, electrophilic bromination on this ring would give predominantly the meta product. - Phenoxy ring: The oxygen of the ester is directly attached to this ring. The -O- lone pairs donate electron density into the phenoxy ring by resonance, making the oxygen an ortho/para director and activating the ring toward electrophilic aromatic substitution. The phenoxy ring is therefore more reactive than the acyl ring. Step 3 - Determine which ring reacts preferentially. The phenoxy ring is activated by the oxygen (electron donation via resonance), while the acyl ring is deactivated by the carbonyl. Electrophilic bromination will occur predominantly on the more activated phenoxy ring. Step 4 - Determine the position on the phenoxy ring. The -OOC- substituent on the phenoxy ring directs ortho/para. Para substitution is favored over ortho due to steric effects. Therefore, the major product has Br at the para position of the phenoxy ring. Step 5 - Match to options. Option (d) shows the unsubstituted benzoyl ring connected via COO to a phenyl ring with Br at the para position - this corresponds to para-bromination on the phenoxy ring. Step 6 - Eliminate other options. (a) Br ortho on acyl ring - wrong ring and wrong position. (b) Br meta on phenoxy ring - wrong position (meta direction would occur on acyl ring, not phenoxy). (c) Br para on acyl ring - wrong ring (acyl ring is deactivated). Therefore, the correct answer is D.