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CHEM103: Organic Chemistry I

Unit 7: Alkynes   In this unit, you will learn about alkynes, which are molecules characterized by a triple carbon-carbon bond.  This particular bond confers unique reactivity to alkynes, such as the capability of forming stable salts with alkaline metal.

Unit 7 Time Advisory
This unit will take you 12 hours to complete.

☐    Subunit 7.1: 4 hours

☐    Subunit 7.2: 8 hours

☐    Sub-subunit 7.2.1: 0.75 hour

☐    Sub-subunit 7.2.2: 0.75 hour

☐    Sub-subunit 7.2.3: 1 hour

☐    Sub-subunit 7.2.4: 0.50 hour

☐    Sub-subunit 7.2.5: 1 hour

☐    Sub-subunit 7.2.6: 0.75 hour

☐    Sub-subunit 7.2.7: 1 hour

☐    Sub-subunit 7.2.8: 0.75 hour

☐    Sub-subunit 7.2.9: 0.75 hour

☐    Sub-subunit 7.2.10: 0.75 hour

Unit7 Learning Outcomes
Upon successful completion of this unit, the student will be able to:

  • Derive the name of alkynes from their molecular structure and vice versa. 
  • Estimate the acidity (pKa) of terminal alkynes.
  • Describe typical alkyne synthesis and reactions, especially the mechanism of synthesis by elimination and electrophilic addition reactions to the carbon-carbon triple bond.  

7.1 Nomenclature, Structural and Physical Properties   7.1.1 Nomenclature of Alkynes   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nomenclature: IUPAC Rules for Alkyne Nomenclature" Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Nomenclature: IUPAC Rules for Alkyne Nomenclature” (HTML)
 
Instructions: Read the box “IUPAC Rules for Alkyne Nomenclature.”  Examples can be found by following the link just below the box.  Look at the examples in the Illustrations 6 and 7.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.  

7.1.2 Properties of Alkynes   - Reading: University of California, Davis: UC Davis ChemWiki: "Properties and Bonding in the Alkynes" Link: University of California, Davis: UC Davis ChemWiki: "Properties and Bonding in the Alkynes” (HTML or PDF)
 
Instructions: Read the entire webpage.
 
Note: You can view this as a PDF by clicking the “Make PDF” button near the top of the linked webpage.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.

7.2 Synthesis and Reactivity of Alkynes   - Reading: University of California, Davis: UC Davis ChemWiki: "Alkynes" Link: University of California, Davis: UC Davis ChemWiki: "Alkynes” (HTML or PDF)
 
Instructions: In the table of contents, select the following reactions and review the corresponding webpage: “Preparation of Alkynes from Alkynyl Anions” and “Preparation of Alkynes by Double Elimination.”  Click the first link and read the linked PPT file for a presentation on the preparation of alkynes from alkynyl anions.  Then, click the second link.  This will take you to a webpage that reviews the synthesis of alkynes by double elimination.  Go through the readings under links 1 through 4.  When you have completed the readings, try the practice problems, under “In the Lab.”  Then, check your answers by clicking on the “Answers” link.  This resource covers subunits 7.2.1 through 7.2.2.
 
Note: Each page is available as a PDF by clicking the “Make PDF” button near the top of the page.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above. 

  • Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reaction of Alkynes" Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reaction of Alkynes" (HTML)
     
    Instructions: Read this webpage in its entirety.  This resource covers subunits 7.2.1 through 7.2.10.
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpage above. 

  • Web Media: YouTube: Freelanceteacher’s “Alkyne Synthesis and Reactions” Link: YouTube: Freelanceteacher’s “Alkyne Synthesis and Reactions" (YouTube)
     
    Instructions: Watch this video #1 to start learning about alkynes.  On the right column of the YouTube page under "suggestions," you can find the link to the remaining videos on this topic produced by the Freelanceteacher.  You can watch videos 1-10 for an in-depth lecture on alkynes.  This resource covers subunits 7.2.1 through 7.2.10.
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.  

  • Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkynes: Practice Problem” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alkynes: Practice Problems” (HTML)
     
    Instructions: Select and complete all the problems from the scroll-down menu.  This resource covers the topics outlined in subunits 7.2.1 through 7.2.10.
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpages above.  

7.2.1 Preparation of Alkynes from Alkynyl Anions   7.2.2 Preparation of Alkynes by Double Elimination   7.2.3 Electrophilic Addition Reactions   7.2.4 Hydrogenation   7.2.5 Hydration and Tautomerism   7.2.6 Hydroboration   7.2.7 Nucleophilic Addition & Reduction   7.2.8 Oxidative Cleavage   7.2.9 Acidity of Alkynes and the Acetylide Anion   7.2.10 Carbon-Carbon Bond Formation Using Acetylide Anions