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CHEM104: Organic Chemistry II

Unit 1: Ethers and Epoxides   Ethers can be distinguished by their carbon-oxygen-carbon bridge (C-O-C).  Ethers are often used as solvents in organic reactions that require polar, aprotic solvents (solvents that have no exchangeable or reactivehydrogens), such as reactions involving Grignard's reagents and alkyllithium reagents.  Ethers show superior stability towardsreducing agents and are thus often chosen as solvents for reduction reactions involving metal hydrides and other reducing metals.  Polymers with an "ether" structure, such as polyethylene glycol (PEG), are important in the pharmaceutical industry, because they confer solubility to certain drug molecules, thus enhancing these drugs' absorbance and efficacy.  Epoxides are ethers characterized by a "tri-atomic," cyclic C-O-C group.  This cyclic ether group is usually incorporated into larger structures to confer certain special physical properties or a particular reactivity to the overall molecule.  For example, the high reactivity of the epoxide ring is the basis of many glues and adhesives.

Unit 1 Time Advisory
This unit will take you 8.75 hours to complete.

☐    Subunit 1.1: 1.25 hours

☐    Subunit 1.2: 2 hours

☐    Subunit 1.3: 1.5 hours

☐    Subunit 1.4: 4 hours ☐    Reading: 0.5 hour

☐    Web Media: 3 hours

☐    Assignment: 0.5 hour

Unit1 Learning Outcomes
Upon successful completion of this unit, the student will be able to:
- Derive the name of an ether or epoxide from its molecular structure, and vice versa. - Plan the synthesis of a given ether, indicating the necessary reagents and reaction conditions. - Plan the conversion of ethers into other chemical compounds using the appropriate reagents and reaction conditions. - Distinguish epoxides from other ethers; use epoxides as reagents in the synthesis of other chemical compounds.

1.1 Nomenclature of Ethers   - Lecture: Khan Academy’s “Ether Naming and Introduction” and “Cyclic Ethers and Epoxide Naming” Link: Khan Academy’s “Ether Naming and Introduction” and “Cyclic Ethers and Epoxide Naming” (YouTube)

 Instructions: Please click on the links above, and watch the two
video lectures (11 minutes and 8 minutes, respectively) to learn
about ethers and how to name them.  Ethers are organic molecules
which have an oxygen bonded to two alkyl groups.  The general
formula is R-O-R', where the R and R’ are alkyl groups.  R and R’
can be the same or different alkyl groups.   

 Viewing these lectures and pausing to take notes should take
approximately 30 minutes to complete.  

 Terms of Use: These videos are licensed under a [Creative Commons
Attribution-NonCommercial-NoDerives United States License
3.0](http://www.saylor.org/site/wp-admin/edit.php?post_type=courses&page=say_manage_courses&cmd=units&pid=52600).
 They are attributed to the Khan Academy. 
  • Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Ethers: Nomenclature” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry:Ethers: Nomenclature” (HTML)

    Instructions: Read only the section on nomenclature of ethers to continue learning about how to name ethers. In organic chemistry, ethers and alkanes are treated similarly in the IUPAC system of nomenclature. Ethers are named based on the parent alkane using the IUPAC system of naming.

    Reading this section should take approximately 15 minutes to complete.
     
    Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License. It is attributed to Professor William Reusch, and the original version can be found here.

  • Reading: University of California, Davis: UC Davis ChemWiki: "Nomenclature of Ethers" Link: University of California, Davis: UC Davis ChemWiki: "Nomenclature of Ethers" (HTML)
     
    Instructions: Read this tutorial and complete the practice problems. 

    Reading this tutorial and completing the practice problems should take approximately 30 minutes.

    Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommerical-ShareAlike 3.0 License. It is attributed to the University of California, Davis, ChemWiki, and the original version can be found here.

1.2 Preparation of Ethers   - Web Media: YouTube: Freelanceteach’s "Organic Chemistry: Ethers (1)" and "Organic Chemistry: Ethers (2)" Link: YouTube: Freelanceteach’s "Organic Chemistry: Ethers (1)" (YouTube) and "Organic Chemistry: Ethers (2)" (YouTube)
 
Instructions: Watch the videos linked above in their entirety ((10:48 and 10:37 minutes, respectively) to start learning about ether synthesis via the Williamson Ether Synthesis.  Although ethers can be synthesized in a number of ways, the Williamson Ether Synthesis is the preferred method of synthesis.  This is because it is the fastest and easiest method of synthesis.
 
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. 
  • Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Ethers (3);” “Organic Chemistry: Ethers (4);” “Organic Chemistry: Ethers (5);” and “Organic Chemistry: Ethers (6)” Links: YouTube: Freelanceteach’s “Organic Chemistry: Ethers (3);” “Organic Chemistry: Ethers (4);” “Organic Chemistry: Ethers (5);” and “Organic Chemistry: Ethers (6)” (YouTube)
     
    Instructions: Please note that these video lectures are optional.  For more information on ethers and their preparation, you may choose to click on the links above and watch all of these videos Organic Chemistry: Ethers 3-6.  Each video is approximately 11 minutes. This material is not required for successful completion of the course. 

    Viewing these optional 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: “Ether Synthesis” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Ether Synthesis” (HTML)

    Instructions: Read the section on Preparation of Ethers. Ethers are typically synthesized from alcohols or their conjugate bases via an SN2 reaction. The Williamson Ether Synthesis is an import reaction of this type to synthesize ethers.

    Reading this section should take approximately 15 minutes to complete.

    Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License. It is attributed to Professor William Reusch, and the original version can be found here.

  • Reading: University of California, Davis: UC Davis ChemWiki: "Williamson Ether Synthesis" Link: University of California, Davis: UC Davis ChemWiki: "Williamson Ether Synthesis" (HTML)
     
    Instructions: Read this tutorial and complete the practice problems on the Williamson Ether synthesis. Note that this reaction is a type of SN2 reaction covered in CHEM103.
     
    Reading this tutorial and completing the problems should take approximately 30 minutes.

    Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 License. It is attributed to the University of California, Davis, ChemWiki, and the original version can be found here.

1.3 Reactions of Ethers   - Web Media: YouTube: Freelanceteach’s "Organic Chemistry: Ethers (7)" and "Organic Chemistry: Ethers (8)" Link: YouTube: Freelanceteach’s "Organic Chemistry: Ethers (7)" (YouTube) and "Organic Chemistry: Ethers (8)" (YouTube)
 
Instructions: Please click on the links above, and watch these lectures in their entirety (10:38 minutes each) to begin to learn about ether reactions.  The two major reaction types of ethers covered here are acid cleavage and peroxide formation.
 
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.

  • Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Ethers (9);” “Organic Chemistry: Ethers (10);” and “Organic Chemistry: Ethers (11)” Links: YouTube: Freelanceteach’s “Organic Chemistry: Ethers (9);” “Organic Chemistry: Ethers (10);” and “Organic Chemistry: Ethers (11)” (YouTube)
     
    Instructions: Please note that these video lectures are optional.  For more information on ethers and their reactions, you may choose to click on the links above and watch these videos Organic Chemistry: Ethers 9-11.  The run times for these videos are 11 minutes, 11 minutes, and 5 minutes respectively. This material is not required for successful completion of the course. 
     
    Viewing these optional 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: “Reactions of Ethers” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Ether” (HTML)
     
    Instructions: Read the section on Reactions of Ethers. Ethers are relatively unreactive. As a result they make stable solvents for many organic compounds. Ethers are inert by nature because they do not have the O-H bond. 
     
    Reading this section should take approximately 15 minutes to complete.
     
    Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License. It is attributed to Professor William Reusch, and the original version can be found here.

  • 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: Follow the instructions on the webpage and work through the whole problem set.

    Completing this assessment should take approximately 15 minutes.

    Terms of Use: This resource is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License. It is attributed to Professor William Reusch, and the original version can be found here.

1.4 Chemistry of Epoxides   - Web Media: YouTube: Freelanceteach’s “Oxacyclopropanes, also known as epoxides (1)” and “Oxacyclopropanes, also known as epoxides (2)” Link: YouTube: Freelanceteach’s "Oxacyclopropanes, also known as epoxides (1)" (YouTube) and "Oxacyclopropanes, also known as epoxides (2)” (YouTube)
 
Instructions: Please click on the links above, and watchthe videos in their entirety (10:59 and 10:40 minutes, respectively) to begin learning about the chemistry of epoxides.  Note that an oxacyclopropane is simply a three-membered ring cyclopropane with a carbon replaced by an oxygen.

 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 webpage(s) above.