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CHEM104: Organic Chemistry II

Unit 8: Carboxylic Acid Derivatives: Esters, Amides, Anhydrides, and Acyl Halides   Substitution of the OH group in carboxylic acids can yield a variety of products, including esters, amides, anhydrides, and acyl halides.  This unit explores the physical and chemical properties of these derivatives.

Unit 8 Time Advisory
This unit will take you 10.75 hours to complete.

☐    Subunit 8.1: 2 hours

☐    Subunit 8.2: 6.75 hours ☐    Reading: 3 hours

☐    Lecture: 0.5 hour

☐    Web Media: 3.25 hours

☐    Subunit 8.3: 2 hours

Unit8 Learning Outcomes
Upon successful completion of this unit, the student will be able to:
- Derive the name of carboxylic acid derivatives from their molecular structure, and vice versa. - Estimate the solubility of a carboxylic acid derivative based on its molecular structure. - Describe the mechanism, reagents involved, and conditions for the reaction of carboxylic acid derivatives, including acyl group substitution reactions, reduction reactions, and reactions with organometallic compounds.

8.1 Nomenclature, Structural, and Physical Properties   - Web Media: YouTube: Freelanceteach’s “Nomenclature of Carboxylic Acid Derivatives (1)” Link: YouTube: Freelanceteach’s “Nomenclature of Carboxylic Acid Derivatives (1)” (YouTube)

 Instructions:  Watch this video (\#1) in its entirety (9:46
minutes) to start learning about the nomenclature of carboxylic acid
derivatives.   
    
 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 webpages above. 
  • Web Media: YouTube: Freelanceteach’s “Nomenclature of Carboxylic Acid Derivatives (2);” “Nomenclature of Carboxylic Acid Derivatives (3);” “Nomenclature of Carboxylic Acid Derivatives (4);” and “Nomenclature of Carboxylic Acid Derivatives (5)”  Links: YouTube: Freelanceteach’s “Nomenclature of Carboxylic Acid Derivatives (2);” “Nomenclature of Carboxylic Acid Derivatives (3);” “Nomenclature of Carboxylic Acid Derivatives (4);” and “Nomenclature of Carboxylic Acid Derivatives (5)” (YouTube)
     
    Instructions: Please note that these video lectures are optional.  For more review of naming carboxylic acid derivatives, you may choose to click on the links above and watch lectures 2-5.  These lectures vary in run time from 2-11 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.

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

    Instructions: Please click on the link above, and read the first section of the webpage titled “Carboxylic Acid Derivatives.”  This section covers “Background and Properties” and “Nomenclature.”  We have learned that carboxylic acids are organic molecules which have a hydroxyl group bonded to an acyl group.  In derivatives of functional, the –OH group is substituted by groups like halo, alkoxyl, and amino.

    This reading should take approximately 45 minutes to complete.

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

  • Lecture: Khan Academy’s “Amides, Anhydrides, Esters, and Acyl Chlorides” Link: Khan Academy:’s “Amides, Anhydrides, Esters, and Acyl Chlorides” (YouTube)

    Instructions: Please click on the link above, and watch the video lecture to reinforce the material covered in the reading. 

    Viewing this lecture and pausing to take notes 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. 

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

 Instructions: Please click on the link above, and read the section
titled "Reactions" on this "Carboxylic Acid Derivatives” webpage. At
the bottom of the page, do not click on Part II.  You will continue
reading on to Part II of this chapter later in another unit in this
course.  The order of reactivity of the carboxylic acid derivatives
are: acyl halides \> anhydrides \>\> esters ≈ acids \>\> amides.  In
this subunit, you will learn how to carry out the reactions of the
acyl group substitution, which is the most important reaction of
carboxylic acid derivatives, as well as all the other reactions.
Make sure to click on any embedded links to read about associated
content.  

 Reading and taking notes should take approximately 3 hours to
complete.  

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

8.3 Problem Solving with Carboxylic Acid Derivatives   - 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: Please click on the link above.  Choose a practice problem from the drop down menu, and follow the instructions on each webpage.  This resource covers the topics outlined in subunits 8.1-8.4.
 
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.