Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
In the given reaction sequence: C ₆ H ₅ OCOCH ₃ AlCl ₃ / (A) I ₂ / NaOH (B) + CHI ₃ The major product (B) is:
Options
- AC ₆ H ₅ COOH
- BC ₆ H ₅ COONa
Correct answer
A. C ₆ H ₅ COOH
Step-by-step solution
The given reaction sequence involves two main steps: 1. Fries Rearrangement: When phenyl acetate ( C ₆ H ₅ OCOCH ₃ ) is heated with anhydrous AlCl ₃ , it undergoes Fries rearrangement. At higher temperatures (indicated by ), the thermodynamically more stable ortho-isomer is formed as the major product due to intramolecular hydrogen bonding. Thus, product (A) is o -hydroxyacetophenone. 2. Iodoform Reaction: The product (A), o -hydroxyacetophenone, contains a methyl ketone group ( - COCH ₃ ). When treated with I ₂ an