In a set of the given reactions, acetic acid yielded a product C. CH3COOH + PCl5 A [Anh. AlCl3]C6H6 B [ether]C2H5MgBr C Product C would be
- CH3CH(OH)C2H5
- CH3COC6H5
- CH3CH(OH)C6H5
- CH3- C2H5 |C(OH)C6H5
Answer
(4) CH3- C2H5 |C(OH)C6H5
Solution
CH3COOH + PCl5 CH3COCl (A) + POCl3 + HCl
Friedel–Crafts acylation: CH3COCl + C6H6 Anh. AlCl3 CH3COC6H5 (B) + HCl
Grignard addition to the ketone, then hydrolysis of the adduct, gives a 3° alcohol:
CH3COC6H5 C2H5MgBr CH3C(C2H5)(OMgBr)C6H5
H2O CH3C(C2H5)(OH)C6H5 (C)
C is 2-phenylbutan-2-ol.
Answer: (4)