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CHEM201: Advanced Organic Chemistry

Unit 3: Organometallics and Heterocycles   Remember that organometallics is the study of metals bonded to nonmetals, and there is an overlap of studying organometallics in both organic and inorganic chemistry.  In your previous organic chemistry courses, you have seen organometallic reagents in the form of Grignards, metal hydrides, and so forth.  Here, we will discuss organometallics more in depth, more specifically as carbon nucleophiles.  We will then examine the classes of organic heterocyclic compounds, which are compounds that contain at least two different elements as ring-member atoms. 

Unit 3 Time Advisory
This unit should take you approximately 9.5 hours to complete.

☐    Subunit 3.1: 4.5 hours

☐    Subunit 3.1.1: 4.5 hours

☐    Subunit 3.1.1.1: 2 hours

☐    Subunit 3.1.1.2: 2.5 hours

☐    Subunit 3.2: 5 hours

☐    Subunit 3.2.1: 0.5 hours

☐    Subunit 3.2.2: 0.5 hours

☐    Subunit 3.2.3: 0.5 hours

☐    Subunit 3.2.4: 0.5 hours

☐    Subunit 3.2.5: 0.5 hours

☐    Subunit 3.2.6: 0.5 hours

☐    Subunit 3.2.7: 0.5 hours

☐    Subunit 3.2.8: 0.5 hours

☐    Subunit 3.2.9: 0.5 hours

☐    Subunit 3.2.10: 0.5 hours

Unit3 Learning Outcomes
Upon successful completion of this unit, the student will be able to:

  • Define organometallic chemistry.
  • Identify organometallic compounds.
  • Explain the reactions of organometallic compounds.
  • Identity heterocyclic compounds.
  • Name heterocyclic compounds.

3.1 Organometallics   - Reading: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Organometallic Compounds” Link: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Organometallic Compounds” (HTML)
 
Instructions: Please read the section titled “Organometallic Compounds” to gain a general understanding of this very complex class of compounds.  Please also click on the links on the page to gain a more in-depth understanding of this class of compounds.  The links will also provide rules for nomenclature, the general structure and reactivity of this class of compounds.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.

3.1.1 Organometallics as Carbon Nucleophiles   - Reading: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Reactivity of Organometallics” Link: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Reactivity of Organometallics” (HTML)
 
Instructions: Please read the section titled “Reactivity of Organometallics” to gain a general understanding of the mechanism behind the reactions of organometallic compounds.  This section shows an overview of all reactions involving organometallic compounds.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.

3.1.1.1 Addition to Carbonyls   - Reading: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Reactions of RLi and RMgX with Aldehydes and Ketones” Link: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Reactions of RLi and RMgX with Aldehydes and Ketones” (HTML)
 
Instructions: Please read the section titled “Reactions of RLi and RMgX with Aldehydes and Ketones” to gain a general understanding of the mechanism behind the reaction of organometallic compounds with compounds containing a carbonyl group.  Pay close attention to the stereoselective effects and transition states (especially chair-like transition states) of the reaction mechanisms.           
 
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3.1.1.2 Conjugate Addition   - Reading: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Conjugate Addition Reactions” Link: University of Calgary: Professor Ian Hunt’s “Organic Chemistry: Conjugate Addition Reactions” (HTML)
 
Instructions: Please read the section titled “Conjugate Addition Reactions” to gain a general understanding of the mechanism behind the conjugate addition reaction of organometallic compounds to b-unsaturated carbonyl containing compounds.  Please click on the forward arrow at the bottom of the page to get a more detailed explanation of the mechanism of conjugate addition reactions.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.

  • Assessment: The Saylor Foundation’s “Organometallic Chemistry in Action” Link: The Saylor Foundation’s “Organometallic Chemistry in Action” (PDF)
     
    Instructions: Please complete the entire assessment.  You can check your answers with the answer key provided here. (PDF)

3.2 Classes of Organic Heterocyclic Compounds   - Reading: Michigan State University: Professor William Reusch’s “Virtual Textbook of Organic Chemistry: Heterocyclic Chemistry: Heterocyclic Compounds” Link: Michigan State University: Professor William Reusch’s “Virtual Textbook of Organic Chemistry: Heterocyclic Chemistry: Heterocyclic Compounds” (HTML)
 
Instructions: Read the entire webpage on heterocyclic compounds linked here for an overview on heterocyclic chemistry and heterocyclic compounds.  You may also want to click the hyperlinks in the online text to review some of the terms and further your reading.
 
Note on the Text: All of the specific compounds in subunits 3.2.1 through 3.2.10 are discussed in this text.  This virtual textbook is hosted by the Michigan State University’s Department of Chemistry.
 
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.

3.2.1 Pyridine   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyridines are presented.

3.2.2 Quinoline   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of quinolines are presented.

3.2.3 Isoquinoline   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of isoquinolines are presented.

3.2.4 Pyrroles   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyrroles are presented.

3.2.5 Azoles   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of azoles are presented.

3.2.6 Furan   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of furans are presented.

3.2.7 Thiophene   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of thiophenes are presented.

3.2.8 Pyridazine   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyridazines are presented.

3.2.9 Pyrimidine   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyrimidines are presented.

3.2.10 Pyrazine   Note: This subunit is covered by the reading assigned beneath subunit 3.2.  Nomenclature and preparation of pyrazines are presented.

  • Assessment: The Saylor Foundation’s “Heterocycles” Link: The Saylor Foundation’s “Heterocycles” (PDF)

    Instructions: Please complete the entire assessment.  You can check your answers with the answer key provided here. (PDF)