Mission 06 - Synthesis of p-Nitroacetanilide

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Across
  1. 6. Nitrogen-based electrophilic ion that attacks the benzene ring. It is formed by the mixture of concentrated nitric and sulfuric acids.
  2. 7. p-Nitroacetanilide has a _________ point higher than acetanilide.
  3. 9. Acetanilide has a substituent group on the benzene ring that directs new electrophilic substitutions to the ortho and _______ positions.
  4. 11. Name of the substitution reaction used to prepare p-nitroacetanilide from acetanilide.
  5. 13. Type of substitution reaction that benzene undergoes.
  6. 14. Function of sulfuric acid in the nitration reaction of acetanilide.
  7. 15. Funnel used for vacuum filtration.
  8. 17. The acetamide group is considered an __________ group in relation to the aromatic ring since nitrogen has a lone pair of electrons that can be donated.
  9. 18. In aromatic nitrations, it directly influences the orientation of the nitro group, especially in substituted aromatic derivatives, leading to the formation of undesirable isomers. For this reason, an ice bath is used.
  10. 19. The ice bath prevents excessive temperature increases due to the __________ of heat during the reaction.
  11. 20. The addition of nitric acid in the presence of the glacial acetic acid/sulfuric acid mixture promotes the ionization of HNO₃, leading to the formation of the __________ nitronium ion (NO₂⁺).
Down
  1. 1. Equipment used to evaporate water under heating.
  2. 2. Glassware used for vacuum filtration.
  3. 3. In the preparation of p-acetanilide, it is expected that in an electrophilic substitution reaction, addition occurs more toward the ortho position than para, as there are two ways for ortho addition (left or right). However, ortho positions experience steric __________, whereas the para position does not.
  4. 4. The gas _________ complexes with Fe²⁺ ions, forming a coordination compound with the formula [Fe(NH₃)₆]²⁺.
  5. 5. A solution of __________ ferrous sulfate is obtained by dissolving ferrous sulfate (FeSO₄) in an aqueous ammonia solution (NH₄OH).
  6. 8. The presence of the nitro derivative is revealed by the oxidation of ferrous ions (Fe²⁺) to __________ ions (Fe³⁺), observed by a color change in the precipitate to reddish-brown within 1 minute.
  7. 10. Name of the substituent group in the acetanilide molecule.
  8. 12. Used to create suction in the Kitasato flask.
  9. 16. How aromatic hydrocarbons are known.