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What would be the product(s) of this reaction if toluene replaced methyl benzoate? If only concentrated...

  1. What would be the product(s) of this reaction if toluene replaced methyl benzoate?
  2. If only concentrated nitric acid were used in this reaction, will that increase the % yield of the reaction? And why? What is the function of concentrated sulfuric acid? Please use a reaction equation to show your answer.

These are questions from my organic chemistry lab regarding the nitration of methyl benzoate to form m-nitrobenzoate through electrophilic aromatic substitution rxn.

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Answer #1

# Since toluene is an ortho - para directing group, we get a mixture of ortho and para products.

# If only conc. HNO3 used, %yield would DECREASE because sulphuric acid helps in generation of electrophile (nitronium ion). If there will be less electrophile, less product will form.

# Conc. Sulphuric acid helps in generation of electrophile as depicted through the mechanism.

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