2009 8 Carboxylic acids II - Carboxylic Acid Family...

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Carboxylic Acid Family Reactions Part 2-Chapters 21-23 Test 1 Answers now posted on website! http://http-server.carleton.ca/~pbuist/
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The Carboxylic Acid Family 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
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Top 10 reactions of Carboxylic Acid and Derivatives 1. Hydro lysis 2. Synthesis of acid chlorides 3. Synthesis of acid anhydrides 5. Synthesis of Amides 6. Synthesis of Alcohols (3 ° ) 7. Reduction of Acyl erivatives 4. Synthesis of esters a) Fischer esterification b) Synthesis of esters via acid chlorides c) Synthesis of esters via anhydrides derivatives 8. Alkylation of β -keto esters or diesters 9. Claisen Reaction (like Aldol) 10. Decarboxylation of β -keto acids
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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
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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
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Reaction 1 : Hydrolysis X O OH O HX O H 2 + O O O OH O O H O O H 2 + A B Increasin 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 ng Reactivity
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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
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Mechanism (Nucleophilic Acyl Substitution) R Cl O OH 2 Cl O R O H H + R OH O R O O H H + HCl + Cl- O R R O O H 2 O O R R O O H 2 O + R OH O R O O R O O H H 2 +
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This note was uploaded on 07/28/2009 for the course ORGANIC CH CHEM 2204 taught by Professor Dr.levin during the Winter '08 term at Indian Institute of Technology, Chennai.

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2009 8 Carboxylic acids II - Carboxylic Acid Family...

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