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Carboxylic Acids: Properties and Synthesis. Chapter 18. Assignments. In-text problems: 18-1 and 18-2 18-4 (IUPAC only!!) 18-6 to 18-10 18-14 to 18-20 End-of-chapter problems: 1 3 to 9 11 to 16 . Sect. 18.1: IUPAC Nomenclature. -oic acid IUPAC ending

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assignments
Assignments
  • In-text problems:
    • 18-1 and 18-2
    • 18-4 (IUPAC only!!)
    • 18-6 to 18-10 18-14 to 18-20
  • End-of-chapter problems:
    • 1
    • 3 to 9
    • 11 to 16

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sect 18 1 iupac nomenclature
Sect. 18.1: IUPAC Nomenclature
  • -oic acid IUPAC ending
  • -carboxylic acid IUPAC ending for ring compounds

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slide4
3-Methylbutanoic acid

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slide9
Benzoic acid

or Benzenecarboxylic acid

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slide10

Numbering system

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slide11

2-chlorobenzoic acid

or 2-chlorobenzenecarboxylic acid

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slide13

Common names!

ortho-chlorobenzoic acid

o-chlorobenzoic acid

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slide14

IUPAC only

3-chloro-2-nitrobenzoic acid

or 3-chloro-2-nitrobenzenecarboxylic acid

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slide15

IUPAC only

3-(3-nitrophenyl)propanoic acid

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common names
Common Names

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some more common names
Some more common names
  • butyric acidand isobutyric acid
  • valeric acid and isovaleric acid
  • Fatty acids: myristic, palmitic and stearic acids

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slide18
2-Methylpropanoic acid

Isobutyric acid

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slide19

Fatty acids

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sect 18 2 carboxylate salts
Sect. 18.2: carboxylate salts
  • endings: oate
  • combine with sodium, potassium etc.
  • Example: sodium butanoate (IUPAC) or sodium butyrate (common)

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sect 18 3 hydrogen bonding
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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sections 18 4 18 5 18 6
Sections 18.4, 18.5, 18.6
  • Much of this material is review!
  • Key table: Table 18-18 on page 62!!
  • Skip Section 18.7.

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slide24

Resonance Effects

Effect Acid Base Examples

Electron

withdrawing by

resonance (-R)

weaken

strengthen

releasing by

Resonance (+R)

Electron

weaken

strengthen

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slide25
Electron-withdrawing effects involving resonance (-R)These substituents strengthen acids and weaken bases on the benzene ring

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slide27
Electron-withdrawing Effects:

strengthen acids

weaken bases

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slide29
Electron releasing effect by resonance (+R)These substituents weaken acids and strengthen bases on the benzene ring

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slide31

Electron-releasing Effects:

    • - weaken acids
    • - strengthen bases

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slide34

Inductive Effect

Effect Acid Base Examples

weaken

Electron

withdrawing by

inductive effect

(-I)

strengthen

electron

releasing by

inductive effect

(+I)

weaken

strengthen

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electron withdrawing by inductive effects i these substituents strengthen acids and weaken bases
Electron withdrawing by inductive effects (-I)These substituents strengthen acids and weaken bases

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slide38

Inductive

and resonance

Inductive, only

Resonance and weak inductive

Benzoic Acid: pKa = 4.19

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another substituted benzoic acid
Another substituted benzoic acid
  • 4-chlorobenzoic acid is weird!! Resonance effect will decrease acidity, but inductive effect wins out.

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slide40
Electron releasing effect by inductive effect (+I)These substituents weaken acids and strengthen bases

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