1. Carboxylic Acids: Properties and Synthesis
Chapter 18
Carboxylic Acids: Properties and Synthesis
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2. Assignments In-text problems: End-of-chapter problems: 18-1 and 18-2
18-4 (IUPAC only!!)
18-6 to to 18-20
End-of-chapter problems: 1
3 to 9
11 to 16
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3. Sect. 18.1: IUPAC Nomenclature
-oic acid IUPAC ending
-carboxylic acid IUPAC ending for ring compounds
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4. 3-Methylbutanoic acid
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5. 2-Chloropentanoic acid
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6. 4-methoxy-3,5-hexadienoic acid
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7. Cyclohexanecarboxylic acid
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8. 3-methylcyclohexanecarboxylic acid
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9. or Benzenecarboxylic acid
Benzoic acid
or Benzenecarboxylic acid
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10. Numbering system
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11. or 2-chlorobenzenecarboxylic acid
2-chlorobenzoic acid
or 2-chlorobenzenecarboxylic acid
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12. Common names for benzoic acids
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13. ortho-chlorobenzoic acid
Common names!
ortho-chlorobenzoic acid
o-chlorobenzoic acid
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14. IUPAC only 3-chloro-2-nitrobenzoic acid
or 3-chloro-2-nitrobenzenecarboxylic acid
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15. IUPAC only
3-(3-nitrophenyl)propanoic acid
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16. Common Names
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17. Some more common names butyric acid and isobutyric acid
valeric acid and isovaleric acid
Fatty acids: myristic, palmitic and stearic acids
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18. 2-Methylpropanoic acid Isobutyric acid
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19. Fatty acids
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20. Sect. 18.2: carboxylate salts
endings: oate
combine with sodium, potassium etc.
Example: sodium butanoate (IUPAC) or sodium butyrate (common)
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21. Carboxylate Ion Formation
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22. Sect. 18.3: hydrogen bonding
Carboxylic acids are very high boiling!
Low MW acids are water soluble and
High MW acids are water insoluble!
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23. Sections 18.4, 18.5, 18.6 Much of this material is review!
Key table: Table on page 62!!
Skip Section 18.7.
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24. Resonance Effects Effect Acid Base Examples Electron weaken strengthen
withdrawing by
resonance (-R)
strengthen
weaken
releasing by
Resonance (+R)
Electron
weaken
strengthen
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25. Electron-withdrawing effects involving resonance (-R) These substituents strengthen acids and weaken bases on the benzene ring
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26. Substituents with Electron-Withdrawing Resonance Effects
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27. Electron-withdrawing Effects:
strengthen acids
weaken bases
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28. A substituted benzoic acid
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29. Electron releasing effect by resonance (+R) These substituents weaken acids and strengthen bases on the benzene ring
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30. Substituents with Electron-Releasing Resonance Effects
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31. Electron-releasing Effects: - weaken acids - strengthen bases
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32. Substituted benzoic acid
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33. Benzoic Acid: pKa = 4.19
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34. Inductive Effect Effect Acid Base Examples Electron withdrawing by
strengthen
weaken
electron
releasing by
inductive effect
(+I)
weaken
strengthen
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35. Electron withdrawing by inductive effects (-I) These substituents strengthen acids and weaken bases
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36. Substituents with Electron-Withdrawing Inductive Effects on substituted acetic acids
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37. WWU- Chemistry

38. Resonance and weak inductive
and resonance
Inductive, only
Resonance and weak inductive
Benzoic Acid: pKa = 4.19
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39. Another substituted benzoic acid
4-chlorobenzoic acid is weird!! Resonance effect will decrease acidity, but inductive effect wins out.
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40. Electron releasing effect by inductive effect (+I) These substituents weaken acids and strengthen bases
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41. Substituents with Electron-Releasing Inductive Effects
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42. WWU- Chemistry

43. Benzoic Acid: pKa = 4.19
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44. Sect. 18.8: Carbonation of Grignard Reagents
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45. Sect. 18.9: Formation of Nitriles
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46. Hydrolysis of Nitriles
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47. Sect. 18.10: Oxidation of Primary Alcohols
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48. Oxidation of Side Chains
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49. WWU- Chemistry