Nitration of Methyl Benzoate

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Chapter 28 Nitration of Methyl Benzoate
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Purpose

• In this experiment a cold solution of an aromatic
  ester that has been in sulfuric acid is reacted
  with nitric acid. This highly exothermic reaction
  is controlled by cooling then the mixture is
  poured on ice .
• The solid product is isolated by filtration and
  washing with water.

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Reaction Mechanism

• The nitration is a typical electrophilic
  substitution reaction. The electrophile is
  nitronium ion (NO2) generated by the reaction of
  concentrated sulfuric and nitric acids.

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Comments

• Follow pp. 432-433 (microscale).
• Follow the lab handout for all experimental
  procedures. Wearing rubber gloves is absolutely
  necessary during this lab! You will work with
  toxic and corrosive acids.
• Perform IR analysis of the product.
• Calculate yield. Moderate yields should be
  achieved.
• (Moles Product / Moles Starting Material) x 100
  Yield

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Safety

• Concentrated H2SO4 and HNO3 are corrosive and
  toxic, wear gloves and handle with care.
• Make sure to slowly add concentrated sulfuric
  acid into the concentrated nitric acid (not vice
  versa!!!). Use extreme caution.