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        • Chapter 19 (MT 1 part 1)
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Chapter 19 (weeks 0-2 of Fall 2019)

CLASS LOGISTICS

This module consists of all of chapter 19, which was covered in week zero through a bit of the first lecture of week two (a bit over three lectures total). Remember to check out peer tutor office hours! Jonathan and I have a lot of experience teaching organic chemistry so I highly recommend that you come to our office hours. 

Chapter 19 Table of Contents
1.) Nomenclature of Carboxylic Acids
2.) Properties of Carboxylic Acids (Acidity, basicity, solubility, boiling point)
3.) Synthesis of Carboxylic Acids (8 reactions)
4.) Reactions of Carboxylic Acids (6 reactions)


Check the reaction summaries tab for a detailed list of reactions. Chapter 19 covers half of midterm 1 (Thursday, 10/24).

Chapter 19: Carboxylic acids

​​Nomenclature of carboxylic acids

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For nomenclature

Synthesis OF CARBOXYLIC ACIDS (8 reactions)

-Mostly review reactions from Che118A/B
Additional reactions to synthesize carboxylic acid: 
1.) Recall that reacting carbonyls with X2, base will cause polysubstitution of the alpha positions). The less substituted (methyl-position) will be substituted first, then act as a leaving group when OH- acts as a nucleophile)
2.) 3 Different reactions from aldehydes: 
-Tollen's Reagent ( 1. AgNO3, NH4OH   2. H3O+) 
-Fehling's Reagent ( 1. Cu2+, OH-    2. H3O+)
-Baeyer Villiger (any peroxycarboxylic acid like MCPBA)
Picture

reactivity of cARBOxylic acid derivatives

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This chart is foundational to Che118C. Understand it well. It shows four carboxylic acid derivatives and their relative reactivity to carboxylic acid. Note that it is easy to form carboxylic acids from anhydrides and acyl chlorides because they are more reactive than carboxylic acids. It is easy to form more stable products from less stable reactants. However, forming carboxylic acids from esters and amides are more difficult and thus require heat. 


​Reactions of Carboxylic acids (6 reactions)

1.) synthesis of acyl chlorides 

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We've seen these reagents in Che 118A! We use these when turning alcohols into alkyl halides
(SN 2 mechanism for primary/secondary alcohols; SN 1 mechanism for tertiary alcohols)

Note: SOCl2 can be used with or without pyridine. Pyridine will increase the yield of our product and also protect us from poisonous HCl gas formation. Professor Nasiri went over mechanisms both with and without pyridine.
The following is the mechanism without pyridine. With pyridine, the pyridine acts as a base to deprotonate the carboxylic alcohol. Then the negative oxygen will act as the nucleophile in the first step rather than the carbonyl. 
Picture

2.) Synthesis of anhydrides

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Professor Nasiri also uses a reaction of two identical carboxylic acids under high heat to form an anhydride

3.) SYNTHESIS OF esters

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4.) SYNTHESIS OF amides

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​5.) Reduction of carboxylic acid by liAlh4

Reduction of carboxylic acids
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NaBH4 is not strong enough to react with COOH (only reacts with acyl halides and anhydrides)

6.) Hell-voldhart zelinsky reaction

In comparison to PBr3, which turns a carboxylic acid into an acyl bromide, trace phosphorus and dibromides (which will combine to form PBr3) will result in addition of Bromine to the alpha position. This occurs because having trace PBr3 will cause PBr3 to react with three carboxylic acids (one for each Br) instead of one. This results in the formation of phosphoric acid, H3PO3, which catalyzes the next step of the mechanism, alpha bromination of the carboxylic acid (see mechanism in ch19 lecture notes for more details). 
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  • Home
  • Courses
    • Organic Chemistry Che118A (Fall 2021) >
      • Che 118A Table of Contents
      • Che118A Introduction
      • Week One
      • Week Two
      • Week Three
      • Week Four
      • Week Five
      • Week Six
      • Spectroscopy Resources >
        • Reactions after MT2
    • Organic Chemistry Che118B (Summer Session) >
      • Che 118B Table of Contents
      • Che118B Introduction
      • Reaction Summaries
      • Week One
      • Week Two
      • Week Three >
        • Lectures (Ch 14-15)
        • Practice Questions
      • Week Four >
        • Lectures (Ch 15-16)
        • Practice (Midterm 2)
      • Week Five >
        • Lectures (Ch 17)
        • Practice Questions
      • Week six >
        • Lectures (Ch 18)
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    • Organic Chemistry Che118C (Quarter-based) >
      • Che 118C Table of Contents
      • Che 118C Introduction
      • Reaction Summaries >
        • Chapter 19 (MT 1 part 1)
        • Chapter 20 (MT 1 Part 2)
        • Chapter 21 (MT 2 Part 1)
        • Chapter 22 (Mt 2 Part 2)
        • Chapter 23 (Final Part 1)
        • Chapter 24 (Final Part 2)
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    • Che 118C >
      • Lievens Organic Chemistry Weebly (Nomenclature, Synthesis, Spectroscopy, and more)
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