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Chapter 20: Functional Derivatives of Carboxylic Acids 20.54 Many types of carbonyl condensation reactions have acquired specialized names, after the 19th century organic chemists who first studied them. Propose mechanisms for the following named condensations: (a) Perkin condensation: Condensation of an aromatic aldehyde with a carboxylic acid anhy- dride. CH,CO, "Na -CH + CH,COĊCH, -CH=CHCOH heat Cinnamic acid (b) Darzens condensation: Condensation of an a-haloester with a ketone or an aromatic aldehyde. For an example, see CHEMISTRY IN ACTION: Industrial Synthesis of Ibu- profen. 1. tert-BuO K* 0 + CICH,ČOC,H, CHČOC,H, 2. H,0 (c) Knoevenagel condensation: Condensation of an aldehyde or ketone with a malonic ester in the presence of an amine-carboxylic acid catalyst. NCH,, CH,CO,H CO,Et CH + E:OCCH,COE1 CH=C CO,Et

Chapter 20: Functional Derivatives of Carboxylic Acids 20.54 Many types of carbonyl condensation reactions have acquired specialized names, after the 19th century organic chemists who first studied them. Propose mechanisms for the following named condensations: (a) Perkin condensation: Condensation of an aromatic aldehyde with a carboxylic acid anhy- dride. CH,CO, "Na -CH + CH,COĊCH, -CH=CHCOH heat Cinnamic acid (b) Darzens condensation: Condensation of an a-haloester with a ketone or an aromatic aldehyde. For an example, see CHEMISTRY IN ACTION: Industrial Synthesis of Ibu- profen. 1. tert-BuO K* 0 + CICH,ČOC,H, CHČOC,H, 2. H,0 (c) Knoevenagel condensation: Condensation of an aldehyde or ketone with a malonic ester in the presence of an amine-carboxylic acid catalyst. NCH,, CH,CO,H CO,Et CH + E:OCCH,COE1 CH=C CO,Et

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.69P
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  1. Many types of carbonyl condensation reactions have acquired specialized names, after the 19th century organic chemists who studied them. Propose mechanisms for the following named condensations:

 

  • Perkin condensation: condensation of an aromatic aldehyde with a carboxylic acid anhydride

 

  • Darzens condensation: Condensation of an α-haloester with a ketone or an aromatic aldehyde. For an example, see CHEMISTRY IN ACTION: Industrial Synthesis of Ibuprofen.

 

  • Knoevenagel condensation: Condensation of an aldehyde or ketone with a malonic ster in the presence of an amine-caboxylic acid catalyst.
Chapter 20: Functional Derivatives of Carboxylic Acids 20.54 Many types of carbonyl condensation reactions have acquired specialized names, after the 19th century organic chemists who first studied them. Propose mechanisms for the following named condensations: (a) Perkin condensation: Condensation of an aromatic aldehyde with a carboxylic acid anhy- dride. -CH + CH,COČCH3 CH,CO, "Na* CH=CHČOH heat Cinnamic acid (b) Darzens condensation: Condensation of an a-haloester with a ketone or an aromatic aldehyde. For an example, see CHEMISTRY IN ACTION: Industrial Synthesis of Ibu- profen. 1. tert-BuO K -0 + CICH,COC,H, CHČOC,H, 2. Н.о (c) Knoevenagel condensation: Condensation of an aldehyde or ketone with a malonic ester in the presence of an amine-carboxylic acid catalyst. NCH,, CH,CO,H CO,Et -CH + E:OCCH,COE -CH=C CO,Et
Transcribed Image Text:Chapter 20: Functional Derivatives of Carboxylic Acids 20.54 Many types of carbonyl condensation reactions have acquired specialized names, after the 19th century organic chemists who first studied them. Propose mechanisms for the following named condensations: (a) Perkin condensation: Condensation of an aromatic aldehyde with a carboxylic acid anhy- dride. -CH + CH,COČCH3 CH,CO, "Na* CH=CHČOH heat Cinnamic acid (b) Darzens condensation: Condensation of an a-haloester with a ketone or an aromatic aldehyde. For an example, see CHEMISTRY IN ACTION: Industrial Synthesis of Ibu- profen. 1. tert-BuO K -0 + CICH,COC,H, CHČOC,H, 2. Н.о (c) Knoevenagel condensation: Condensation of an aldehyde or ketone with a malonic ester in the presence of an amine-carboxylic acid catalyst. NCH,, CH,CO,H CO,Et -CH + E:OCCH,COE -CH=C CO,Et
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