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Experiment 15. Reactions of carboxylic acids

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1. Experiment 15Reactions of Carboxylic Acids 2. Pre-laboratory Questions: 3. DRAW THE STRUCTURAL FORMULAOF THE FOLLOWING COMPOUNDS:Acetic acid, monochloroacetic acid,…
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  • 1. Experiment 15Reactions of Carboxylic Acids
  • 2. Pre-laboratory Questions:
  • 3. DRAW THE STRUCTURAL FORMULAOF THE FOLLOWING COMPOUNDS:Acetic acid, monochloroacetic acid, trichloroaceticacid, benzoic acid, oxalic acid, succinic acid, lacticacid, tartaric acid, citric acid and propionic acid.
  • 4. Acetic acid
  • 5. Monochloroacetic acid
  • 6. Trichloroacetic acid
  • 7. Benzoic acid
  • 8. Oxalic acid
  • 9. Succinic acid
  • 10. Lactic acid
  • 11. Tartaric acid
  • 12. Citric acid
  • 13. Propionic acid
  • 14. WRITE THE EQUATION THAT SHOWSTHE IONIZATION OF VALERIC ACID INWATER.
  • 15. ++HO 2 H3O +
  • 16. WRITE EQUATIONS SHOWING THEREACTIONS OF VALERIC ACID WITHNAOH AND NAHCO3.
  • 17. + NaOH+ NaHCO 3 + CO2 + H2O
  • 18. RESULTS & DISCUSSIONSA. ACIDITY AND STRUCTURE Acetic acid Monochloroacetic Trichloroacetic acid acid pH 3.0 2.0 1.0
  • 19. DISCUSSION: Trichloroacetic acid is more acidic because of the presence of the 3 chlorine atoms which tend to pull the electrons closer leaving the Hydrogen more prone to leave
  • 20. B. SOLUBILITY Water NaHCO3 Acetic Acid - 0.5 mL Benzoic Acid Did not dissolve 0.5 mL Oxalic Acid 0.5 mL 0.5 mL Lactic Acid 0.5 mL 1 mL
  • 21. EFFECT OF OXIDIZING AGENTS KMnO4 Tollens’ Reagent Formic acid Purple to green (w/o heating) Silver mirror formed Green to brown (after heating) Acetic acid No change in color No silver mirror formed Lactic acid Purple to green (w/o heating) No silver mirror formed Green to brown (after heating) Tartaric acid Purple to bloody red (w/o heating) No silver mirror formed Bloody red to clear sol’n (after heating) Citric acid Purple to clear sol’n No silver mirror formed Oxalic acid No change in color No silver mirror formed Benzoic acid No change in color No silver mirror formed Propionic acid Purple to reddish brown (after White precipitate heating) Water No change in color No silver mirror formed
  • 22. FORMIC PROPIONIC TARTARIC CITRIC ACETIC
  • 23. OXALIC LACTIC BENZOIC
  • 24. DISCUSSION for KMnO4 •Carboxylic acids are relatively resistant to oxidation. However, some acids, like alpha-hydroxy acids may be oxidized. Acetic acid Lactic acid
  • 25. DISCUSSION for Tollen’s Reagent• Mild oxidizing agents like Tollen’s reagent are easily reduced by aldehydes to silver mirror. Formic acid O C H OH
  • 26. ESTERIFICATION • Smells like Guava ; • Did not dissolve in waterDISCUSSION: There are two evidences of esterification reactions: 1. The change in solubility – the product ester is not water soluble, so two layers were formed 2. A distinctive change in odor – they are usually sharp and extremely pleasant
  • 27. CARBOXYLIC ACID AND ITS SALTSCold water: salicylic acid did not dissolveHot water: salicylic acid dissolvedWhen cooled to room temperature: crystals were formedAddition of 3M NaOH in erlenmeyer flask: crystals were dissolvedAddition of 3M HCl in erlenmeyer flask: crystals were reformed
  • 28. QUESTIONS
  • 29. 1. What is the effect of Cl on the acidity of carboxylic acids? Cl is electronegative which tends to pullselectrons closer to them leaving the hydrogen more readily to leave making it highly acidic
  • 30. 2. Explain the effect of the structure of the samples used on solubility behavior.
  • 31. Acetic acid
  • 32. Monochloroacetic acid
  • 33. Trichloroacetic acid
  • 34. Benzoic acid
  • 35. Oxalic acid
  • 36. Succinic acid
  • 37. Lactic acid
  • 38. Tartaric acid
  • 39. Citric acid
  • 40. Propionic acid
  • 41. 3. Write the equation showing the ester formation.
  • 42. Conclusion• In conclusion, the structure of the compounds plays an important role in its solubility.• Electronegativity plays a big role on the carboxylic acid’s acidity.• Carboxylic acids are usually resistant to oxidization but there are some cases that they can be oxidized.
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