Exams › JEE Advanced › Chemistry

Phenyl benzoate (Ph-O-CO-Ph) is subjected to Friedel-Crafts chlorination using Cl2/AlCl3. What is the major product?

1. Phenyl benzoate with Cl at the meta position on the benzoyl ring
2. Phenyl benzoate with Cl at the para position on the benzoyl ring
3. Phenyl benzoate with Cl at the para position on the phenoxy ring
4. Phenyl benzoate with Cl at the meta position on the phenoxy ring

Correct answer: Phenyl benzoate with Cl at the meta position on the benzoyl ring

Solution

Phenyl benzoate: the benzoate ring (C6H5-C=O-O-) has the -COO- group as meta director; the phenoxy ring (-O-CO-C6H5) has the -O- as ortho/para director. Under Cl2/AlCl3, electrophilic aromatic substitution occurs preferentially on the more activated ring (phenoxy ring, bearing -O-). Cl substitutes para to -O-, giving the para-chloro phenoxy product. However, if the question intends the structure as Ph-COO-Ph where the left Ph is directly attached to C=O (benzoyl), then the COO- group deactivates and directs meta. Standard JEE treatment: the -OCOR group on phenoxy ring is weakly activating (ortho/para); this ring gets chlorinated at para. So the major product is phenyl benzoate with Cl at para on the phenoxy ring.

Related JEE Advanced Chemistry questions

• When hydrogen halides react with alcohols, alkyl group rearrangement does not typically happen with most primary alcohols. What is the most accurate reason for this?
• Which of the following statements accurately describes the behavior of the given compound?
• Tertiary and secondary carbocations readily participate in elimination reactions when treated with strong alkoxide bases, while aryl and vinyl halides resist nucleophilic substitution. Which of the following reactions is correct?
• Although neopentyl alcohol is a primary alcohol, it follows the SN1 mechanism due to steric hindrance caused by a bulky alkyl group. Identify its structure.
• In the following sequence of reactions, identify the structures of intermediates Y, Z, W, and M: Y --(NaBH4)--> Z --(conc. HBr)--> W Y --(N2H4 / KOH, heat)--> M M --(NBS, heat/light)--> W W --(1) Mg/ether, (2) CO2, (3) H3O+)--> Ph-CH(COOH)-CH2-CH3 Which of the following statements about the intermediates is correct?
• Consider the compound CH3-CH2-CH(X)-CH3, where X is a halogen. When treated with alcoholic KOH and heated, it undergoes elimination to give alkene products. For which choice of X will the proportion of the Hofmann (less substituted) alkene product be the greatest?

⚔️ Practice JEE Advanced Chemistry free + battle 1v1 →