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Last updated 10:55 PM on 6/6/26
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13 Terms

1
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Preparing carboxylic acids (redox/oxidizing agents)

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2
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carboxylic acid reactivity with acid

  • oxygen of carbonyl of carboxylic acid reacts with acid if strong enough acid

<ul><li><p>oxygen of carbonyl of carboxylic acid reacts with acid if strong enough acid</p></li></ul><p></p>
3
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carboxylic acid reactivity with base

  • Nu attacks Carbon of carbonyl

  • if Nu is good enough base, it will deprotanate the OH instead of doing Nu attack

<ul><li><p>Nu attacks Carbon of carbonyl</p></li><li><p>if Nu is good enough base, it will deprotanate the OH instead of doing Nu attack</p></li></ul><p></p>
4
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electron withdrawing groups

  • EWG stabilize base, so conj acid is stronger acid

  • more electroneg substituents make stronger acid (ex F vs Cl, F will make more acidic)

  • proximity effect: the closer the EWG to carbo acid, the stronger the acid is

<ul><li><p>EWG stabilize base, so conj acid is stronger acid</p></li><li><p>more electroneg substituents make stronger acid (ex F vs Cl, F will make more acidic)</p></li><li><p>proximity effect: the closer the EWG to carbo acid, the stronger the acid is</p></li></ul><p></p>
5
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EDG vs EWG

  • EDG destabilize conj base so acid is less acidic

  • EWG stabilize conj bas, and acid is more acidic

<ul><li><p>EDG destabilize conj base so acid is less acidic</p></li><li><p>EWG stabilize conj bas, and acid is more acidic</p></li></ul><p></p>
6
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Nitrile preparation RXN

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7
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Synthesis of Nitriles

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8
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Nitrile RXN’S

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9
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Nitrile Hydrolysis with H2O and acid/base RXN

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10
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Nitrile hydrolysis MECHANISM with base

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11
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Ways to synthesize Carboxylic acids

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12
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DIBAL-H MECHANISM for Nitrile reduction

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13
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Organometallic addition to nitrile MECHANISM

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