JEE Advanced levelSingle correct optionDifficulty 3 of 3co154
Phenyl methyl ketone is treated successively with (i) NaBHX4 in methanol, (ii) excess IX2 and NaOH with warming, and (iii) dilute HCl. The organic acid formed is
Aphenylethanoic acid
B1-phenylethan-1-ol
Cbenzaldehyde
Dbenzoic acid
Answer: D
NaBHX4 gives 1-phenylethan-1-ol, CX6HX5CH(OH)CHX3. Iodine and base oxidise this to CX6HX5COCHX3 and then cleave it by the haloform reaction to CX6HX5COOX− and CHIX3. Acidification gives benzoic acid.