Compound isolated was not 4-chlorobenzoic acid

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Question- A student attempted to prepare 4-chlorbenzoic acid by oxidizing toluene and then chlorinating benzoic acid. The compound she isolated was not 4-chlorobenzoic acid. What was the product and why was it obtained? Suggest a suitable route to the desired product.
If possible just a to the point details about how you got the answer?

Reference no: EM13715842

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