Which of the following give benzoic acid on suitable treatment (heating with the reagent, then acidification where relevant)?

A $C X_{6} H X_{5} CH X_{2} CN$ with dilute $H X_{2} SO X_{4}$ under reflux
B $C X_{6} H X_{5} MgBr$ followed by $CO X_{2}$ and $H X_{3} O X^{+}$
C $C X_{6} H X_{5} C (CH X_{3}) X_{3}$ with hot alkaline $KMnO X_{4}$
D $C X_{6} H X_{5} COCH X_{3}$ with $I X_{2}$ and aqueous $NaOH$

Answer: B, D

Phenyl Grignard with

CO X_{2}

and the haloform reaction of acetophenone both give benzoic acid. tert-Butylbenzene has no benzylic hydrogen and is not oxidised, and phenylethanenitrile hydrolyses to phenylethanoic acid, which has one more carbon.

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Which of the following give benzoic acid on suitable treatment (heating with the reagent, then acidification where relevant)?

Answer: B, D

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