Lecture 5AB - The Carboxylic Acid Family: Part II R X O R O...

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Unformatted text preview: The Carboxylic Acid Family: Part II R X O R O O O Acid chloride R C N R O R O R R N O H R R O O H Acid anhydride Ester Nitrile Amide Lecture 5 Top 10 reactions of Carboxylic Acid and Derivatives 1. Hydro lysis (a-e) 2. Synthesis of acid chlorides 3. Synthesis of acid anhydrides 6. Grignard Reaction 7. Reduction 8. Alkylation of -keto esters or diesters . Claisen Reaction 2 4. Synthesis of esters (a-c) 5. Synthesis of Amides (a,b). 9. Claisen Reaction (like Aldol) 10. Decarboxylation of -keto acids Have to know these for Test 2! Most important Reaction of Carboxylic acid family: Nucleophilic Acyl Substitution O- addition O elimination L Nu Tetrahedral Intermediate L Nu O Nu L- + L = Leaving Group Note: That the SN 2 option is not available - steric hindrance on approach of nucleophile Carboxylic Acid Derivatives are hydrolyzed to give Carboxylic acids O O O O Acid chloride Acid anhydride Ester Nitrile Amide R C N R X R O R O R O R R O O H R N H R H 2 O Reaction 1 : Hydrolysis X O OH O HX O H 2 + O O O OH O O H O O H 2 + A B In c r e a s in O O OH O O H 2 HOCH 3 + N H O OH O O H 2 H 2 NCH 3 + C D OH O O H 2 C N C H 3 NH 3 + E n g R e a c t i v i t y 1ab Hydro lysis of Acid Halides and acid anhydrides is spontaneous R Cl O R OH O OH 2 + HCl a) O R R O O OH 2 R OH O 2 b) Cl- and RCO 2- are good leaving groups Mechanism (Nucleophilic Acyl Substitution) R Cl O OH 2 R OH O R O O H H + HCl + Cl- O R R O O H 2 O R OH O R O O R O O H H 2 + 1c Hydro lysis of most esters is slow O O slow Ester hydrolysis R OR R OH O H 2 ROH + + Need acid catalysis or base to speed up reaction Also use of a water-miscible cosolvent promotes solubility of ester in aqueous phase. Plant Seed Oils H 2 O (hydrolysis) Olive oil + Oleic acid Glycerol Hydrolysis of Fats:...
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Lecture 5AB - The Carboxylic Acid Family: Part II R X O R O...

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