Loading...

CHEM104: Organic Chemistry II

Unit 7: Carboxylic Acids   Carboxylic acids are characterized by the presence of a COOH group in the molecular structure.  This group is called the carboxyl group.  These compounds are the most common acids you will encounter in this organic chemistry course. A few carboxylic acids you may be familiar with are citric acid in fruits and acetic acid in fruits, and lactic acid in spoiled milk.

Unit 7 Time Advisory
This unit will take you 9.75 hours to complete.

☐    Subunit 7.1: 4.25 hours ☐    Reading: 2 hours

☐    Lecture: 0.25 hour

☐    Web Media: 2 hours

☐    Subunit 7.2: 0.75 hour

☐    Subunit 7.3: 2.75 hours

☐    Subunit 7.4: 2 hours

Unit7 Learning Outcomes
Upon successful completion of this unit, the student will be able to:
- Derive the name of carboxylic acids from their molecular structures, and vice versa. - Describe the physical properties of carboxylic acids. - Estimate the acidity (pKa) of a carboxylic acid. - Describe the mechanism, reagents involved, and reaction conditions for the preparation of carboxylic acids. - Describe the reactivity of carboxylic acids including reactions salt formation, substitution, esterification, reduction, and oxidation reactions.

7.1 Nomenclature, Structural, and Physical Properties   - Web Media: YouTube: Freelanceteach’s Naming Aldehydes, Ketones, and Carboxylic Acids (5)” Link: YouTube: Freelanceteach’s “Naming Aldehydes, Ketones, and Carboxylic Acids (5)” (YouTube)
 
Instructions: Please click on the link above, and watch this video (#5) in its entirety (9:16 minutes) to start learning about the nomenclature of aldehydes and ketones.  The video will also give you a review of nomenclature of aldehydes and ketones covered in unit six.
 
Viewing this lecture and pausing to take notes should take approximately 15 minutes to complete.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above. 

  • Web Media: YouTube: Freelanceteach’s “Naming Aldehydes, Ketones, and Carboxylic Acids (6);” “Naming Aldehydes, Ketones, and Carboxylic Acids (7);” and “Naming Aldehydes, Ketones, and Carboxylic Acids (8)” Links: YouTube: Freelanceteach’s  “Naming Aldehydes, Ketones, and Carboxylic Acids (6);” “Naming Aldehydes, Ketones, and Carboxylic Acids (7);” and “Naming Aldehydes, Ketones, and Carboxylic Acids (8)” (YouTube)
     
    Instructions: Please note that these video lectures are optional.  For additional practice naming aldehydes and ketones, you may choose to also click on the links above and watchlectures 6-8.  These video lectures run 4 minutes, 11 minutes, and 2 minutes respectively.  This material is not required for successful completion of the course.
     
    Viewing these lectures and pausing to take notes should take approximately 30 minutes to complete.
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.

  • Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Carboxylic Acids” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Carboxylic Acids” (HTML)

    Instructions: Please click on the link above, and readthe sections titled “Carboxylic Acids” and "Physical Properties and Acidity." 

    Reading and taking notes should take approximately 2 hours to complete.

    Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.   

  • Lecture: Khan Academy’s “Carboxylic Acid Introduction” and “Carboxylic Acid Naming” Link: Khan Academy’s “Carboxylic Acid Introduction” (YouTube) and “Carboxylic Acid Naming” (YouTube)

    Instructions: Please click on the links above, and watch the two video lectures to reinforce the material covered in the reading. 

    Viewing these lectures should take approximately 15 minutes to complete.

    Terms of Use: These videos are licensed under a Creative Commons Attribution-NonCommercial-NoDerives United States License 3.0.  They are attributed to the Khan Academy. 

  • Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Carboxylic Acids (1)” Link: YouTube: Freelanceteach’s “Organic Chemistry: Carboxylic Acids (1)” (YouTube)

    Instructions:  Please click on the link above, and watch this video (#1) in its entirety (10:13 minutes) to learn more about carbohydrate structure and properties.
     
    Viewing this lecture and pausing to take notes should take approximately 15 minutes to complete.

    Terms of Use: Please respect the copyright and terms of use displayed on the webpage above. 

  • Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Carboxylic Acids (2);” “Organic Chemistry: Carboxylic Acids (3);” “Organic Chemistry: Carboxylic Acids (4);” “Organic Chemistry: Carboxylic Acids (5);” and “Organic Chemistry: Carboxylic Acids (6)” Links: YouTube: Freelanceteach’s “Organic Chemistry: Carboxylic Acids (2);” “Organic Chemistry: Carboxylic Acids (3);” “Organic Chemistry: Carboxylic Acids (4);” “Organic Chemistry: Carboxylic Acids (5);” and “Organic Chemistry: Carboxylic Acids (6)” (YouTube)
     
    Instructions: Please note that these video lectures are optional.  For additional information on carbohydrates and their properties and structures, you may choose to click on the links above and watch lectures 2-6.  The run time for these lectures varies from 5-11 minutes.  This material is not required for successful completion of the course.

    Viewing these lectures should take approximately 1 hour to complete.

    Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.

7.2 Preparation of Carboxylic Acids   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Preparation of Carboxylic Acids” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Preparation of Carboxylic Acids" (HTML)

 Instructions:  Read the entire section linked here.  Many of the
reactions used to prepare carboxylic acids are oxidations.  This is
due to the high oxidation state of the carboxyl functional group. 
As we learned in earlier subunits, carboxylic acids can be
synthesized via oxidation of arene substituents, primary alcohols,
alkenes, and alkynes.  

 This reading should take approximately 30 minutes to complete.  

 Terms of Use: Please respect the copyright and terms of use
displayed on the webpage above.                     
  • Web Media: YouTube: Freelanceteach’s “Carboxylic Acids and Acid Derivatives (3),” “Carboxylic Acids and Acid Derivatives (4),” and “Carboxylic Acids and Acid Derivatives (5)” Link: YouTube: Freelanceteach’s “Carboxylic Acids and Acid Derivatives (3),” (YouTube)  “Carboxylic Acids and Acid Derivatives (4),” (YouTube) and “Carboxylic Acids and Acid Derivatives (5)” (YouTube)
     
    Instructions: Please click on the links above, and watchthese three videos (#s 3, 4, 5) in their entirety (5:16, 3:58, and 6:00 minutes, respectively) to start learning how to make carboxylic acids.  The videos walk you through carboxylic acid synthesis by the oxidation of aldehydes or primary alcohols, carbonation with Grignard reagents, and nitrile hydrolysis.

    Viewing these lectures should take approximately 15-20 minutes to complete.

    Terms of Use: Please respect the copyright and terms of use displayed on the webpage above. 

7.3 Reactions of Carboxylic Acids   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Carboxylic Acids” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Reactions of Carboxylic Acids" (HTML)

 Instructions:Please click on the link above, and read the entire
section, “Reactions of Carboxylic Acids.”  Because they are acids,
carboxylic acids react with bases to form salts and also undergo
substitution of the hydroxyl hydrogen.  The hydroxyl group can be
exchanged by a nucleophilic group.  This is the general mechanism
for preparing the various carboxylic acid derivative functional
groups.  You will learn each of the reagents used to convert a
carboxylic acid to the various acid derivatives and the mechanism
involved in these reactions.  

 Reading and taking notes should take approximately 1 hour to
complete.  

 Terms of Use: Please respect the copyright and terms of use
displayed on the webpage above.  
  • Lecture: Khan Academy’s “Fisher Esterification” and “Acid Chloride Formation” Link: Khan Academy’s “Fisher Esterification” (YouTube) and “Acid Chloride Formation” (YouTube)

    Instructions: Please click on the links above, and watch the two video lectures to reinforce the material covered in the reading. 

    Viewing these lectures and pausing to take notes should take approximately 45 minutes to complete.

    Terms of Use: These videos are licensed under a Creative Commons Attribution-NonCommercial-NoDerives United States License 3.0.  They are attributed to the Khan Academy.  

  • Web Media: YouTube: Freelanceteach’s “Carboxylic Acids and Acid Derivatives (7)" Link: YouTube: Freelanceteach’s “Carboxylic Acids and Acid Derivatives (7)” (YouTube)

    Instructions:  Please click on the link above, and watch this video (#7) in its entirety (6:56 minutes) to start learning the general mechanism for carboxylic acid reactions. This resource covers subunits 7.3.
     
    Viewing this lecture and pausing to take notes should take approximately 15 minutes to complete.

    Terms of Use: Please respect the copyright and terms of use displayed on the webpage above. 

  • Web Media: YouTube: Freelanceteach’s “Carboxylic Acids and Acid Derivatives (8);” “Carboxylic Acids and Acid Derivatives (9);” “Carboxylic Acids and Acid Derivatives (10);” and “Carboxylic Acids and Acid Derivatives (11)” Links: YouTube: Freelanceteach’s “Carboxylic Acids and Acid Derivatives (8);” “Carboxylic Acids and Acid Derivatives (9);” “Carboxylic Acids and Acid Derivatives (10);” and “Carboxylic Acids and Acid Derivatives (11)” (YouTube)
     
    Instructions: Please note that these resources are optional.  For a more in-depth study of carboxylic acid reaction mechanisms, you may choose to click on the links above and watch lectures 8-11.  These video lectures range in run time from 4-10 minutes.  This material is not required for successful completion of the course.
     
    Viewing these lectures should take approximately 45 minutes to complete.

    Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.

7.4 Problem Solving with Carboxylic Acids   - Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Practice Problems" Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Practice Problems" (HTML)

 Instructions: Choose a practice problem set from the drop down
menu, and work through all the problems.  Work through all of the
problems on all of the topics.  These problems will give you
practice with nomenclature, acidity, and reactions of carboxylic
acids.  These practice problems covers the topics outlined in
subunits 7.1-7.4.  

 You should dedicate approximately 2 hours to practicing these
problem sets.  

 Terms of Use: Please respect the copyright and terms of use
displayed on the webpage above.