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CHEM103: Organic Chemistry I

Unit 5: Alcohols   Alcohols are characterized by the presence of a hydroxyl group bound to a carbon (C-OH) in the molecular structure.  This is the first family of organic molecules with strong intramolecular forces (hydrogen bonds) you have encountered so far.  Most of the alcohols' physical properties are determined by these forces, such as their relatively high boiling point and high solubility in water.  Simple alcohols are produced in industrial quantities because they find applications in the food and beverage industry (ethanol), cosmetics (ethanol, and isopropanol), antifreezes and cooling systems (methanol), cleaning products, and, more recently, gasoline (where ethanol and butanol are used as additives).  In this unit, you will learn how to name and synthesize alcohols.  You will also read about alcohol’s most common reactions and learn how to use these reactions to convert alcohols into more valuable products. 

Unit 5 Time Advisory
This unit will take you 12.25 hours to complete.

☐    Subunit 5.1: 2.25 hours

☐    Subunit 5.2: 3 hours

☐    Subunit 5.3: 7 hours

☐    Sub-subunit 5.3.1: 1 hour

☐    Sub-subunit 5.3.2: 1 hour       

☐    Sub-subunit 5.3.3: 1 hour       

☐    Sub-subunit 5.3.4: 1 hour       

☐    Sub-subunit 5.3.5: 1 hour       

☐    Sub-subunit 5.3.6: 1 hour       

☐    Sub-subunit 5.3.7: 1 hour        

Unit5 Learning Outcomes
Upon successful completion of this unit, the student will be able to:

  • Derive the name of an alcohol from its molecular structure, and derive the structure of an alcohol from its name.
  • Estimate the acidity of an alcohol from its structure.
  • Synthesize alcohols from starting materials.
  • Plan the conversion of alcohol into other chemical compounds using the appropriate reagents and reaction conditions.

5.1 Nomenclature   - Web Media: Khan Academy: Salman Khan’s “Alcohols” Link: Khan Academy: Salman Khan’s: “Alcohols” (HTML)
 
Instructions: Please watch the video to reinforce material covered in the reading (6:50 minutes).  

 Terms of Use: This resource is licensed under a [Creative Commons
Attribution-NonCommercial-NoDerivs 3.0 Unported
License](http://creativecommons.org/licenses/by-nc-nd/3.0/). It is
attributed to the Khan Academy.
  • Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Alcohol Nomenclature" Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Alcohol Nomenclature" (HTML)
     
    Instructions: Read the section titled "Alcohol Nomenclature."
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above. 

  • Web Media: YouTube: Freelanceteacher’s “Tutorial on Alcohol Nomenclature” Link: YouTube: Freelanceteacher’s “Tutorial on Alcohol Nomenclature" (YouTube)
     
    Instructions: Watch this video lecture in its entirety (10:46 minutes).
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.

5.2 Acidity of Alcohol   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohol" Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohol" (HTML)
 
Instructions: Read the section titled “Alcohol Reactions.”  Then, click the link just below the section on “Alcohol Reactions” for a discussion of “Molecular Structure and Acidity.”
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.  

5.3 Synthesis and Reactions of Alcohols   - Reading: University of California, Davis: UC Davis ChemWiki: "Electrophilic Hydration to Make Alcohols” Link: University of California, Davis: UC Davis ChemWiki: "Electrophilic Hydration to Make Alcohols" (HTML or PDF)
 
Instructions: Read the tutorial webpage, and complete the practice problems.  This resource also covers subunit 5.3.1.  You can view this in a PDF version by clicking the “Make PDF” button at the top of the linked webpage.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.  

  • Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohols” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Reactions of Alcohols” (HTML)
     
    Instructions: Read the entire chapter on alcohol reactions.  Click on the link titled “Oxidation Reactions of Alcohols and Reactions of Phenols” at the bottom of the webpage to continue reading on this topic.  Skip the section titled “Phenols.”  After the Phenol section, you will find some useful practice problems related to alcohols.  From the scroll-down menu, choose the problem topic to test your knowledge of alcohols.  This resource also covers the topics outlined in subunits 5.3.2-5.3.7. 
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.

  • Web Media: YouTube: Mark Rosengarten’s "Chemistry Tutorial 13.3a: Organic Families: Alcohols" Link: YouTube: Mark Rosengarten’s "Chemistry Tutorial 13.3a: Organic Families: Alcohols" (YouTube)
     
    Instructions: Please watch this 8-minute video in its entirety.  This video provides a short overview of alcohols.  This resource covers subunits 5.3.1-5.3.7.
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above.

  • Web Media: YouTube: Freelanceteacher’s "Organic Chemistry: Alcohols (1)" Link: YouTube: Freelanceteacher’s "Organic Chemistry: Alcohols (1)" (YouTube)

    Instructions: Watch this video #1 to start learning about alcohols (about 9:30 minutes).  On the right column of the YouTube page under "suggestions," you can find the link to the remaining videos produced by Freelanceteacher.  You may choose to watch all the 12 videos for an in-depth explanation of the chemistry of alcohols, although this is not required.  This resource covers subunits 5.3.1-5.3.7.
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpage(s) above. 

5.3.1 Synthesis of Alcohols via Electrophilic Hydration   5.3.2 Substitution of the Hydroxyl H   5.3.3 Substitution of the Hydroxyl Group   5.3.4 Elimination of Water (Dehydration of Alcohols)   5.3.5 Oxidation of Alcohols   5.3.6 Conversion of Alcohols into Alkyl Halides and Tosylates   5.3.7 Alcohol’s Reaction with Trimethyl Silane