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CHEM104: Organic Chemistry II

Unit 9: Enols and Enolates and Alpha Substituted Carbons   This short unit will deal with just enols and enolates.  The reactions we will cover in this unit are highly important because they are among the most widely utilized methods of forming newcarbon-carbon bonds.  Most of thesereactions follow the general trend of deprotonating a carbon alpha to a carbonyland subsequently using the alpha carbon as a nucleophile to attack electron-poor molecules or functional groups (electrophiles).

Unit 9 Time Advisory
This unit will take you 7 hours to complete.

☐    Subunit 9.1: 6 hours

☐    Subunit 9.2: 1 hour

Unit9 Learning Outcomes
Upon successful completion of this unit, the student will be able to:
- Estimate the acidity of the alpha hydrogen(s) (pKa). - Describe the mechanism, reagents involved, and conditions for reactions involving the alpha carbon of carbonyl compounds. - Plan the synthesis of complicated molecular structures involving the formation of new carbon-carbon bonds.

9.1 Acidity at the Alpha Carbon and Reactions of Carboxylic Acid Derivatives   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Carboxylic Acid Derivatives: Reactions of the a-Carbon” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Carboxylic Acid Derivatives: Reactions of the a-Carbon” (HTML)

 Instructions: Please click on the link above, and read the entire
section entitled “Reactions of the *a-*Carbon” in the “Carboxylic
Acid Derivatives” chapter.  Carboxylic acid derivatives undergo
electrophilic substitution to form enols and enolate anion
intermediates.  These reactions are similar to the keto enol
tautermer of ketones.  As with the ketone reactions, the carboxylic
acid derivative need to have at least one (alpha) hydrogen on the
alpha carbon.  This resource covers subunits 9.1 and 9.2.  

 Reading and taking notes should take approximately 1 hour to
complete.  
    
 Terms of Use: Please respect the copyright and terms of use
displayed on the webpage above. 

9.2 Problem Solving and Synthesis Applications   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Condensation Reactions in Synthesis" Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: “Condensation Reactions in Synthesis" (HTML)

 Instructions:Please click on the link above, and read through the
entire webpage.  Then, choose a practice problem set from the scroll
down menu, and follow the instructions on each webpage.  Work
through all the problem sets.  Note: This lesson details how you
should approach synthesis in condensation reactions.  In organic
synthesis, complex organic molecules can be produced via a number of
simple reaction steps and appropriate starting materials.  In this
subunit, you will learn how to carry out and use condensation
reactions in synthesis.  This resource covers the topics outlined in
subunits 9.1 and 9.2.  

 Reading and taking notes should take approximately 1 hour to
complete.  

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