Loading...

CHEM104: Organic Chemistry II

Unit 5: Amines   Amines are organic compounds containing a nitrogen atom in a low oxidation state.  This nitrogen retains its lone pair of electrons and the characteristics of a strong Lewis base.  There are other organic compounds that contain nitrogen atoms in their structure, but this nitrogen-based group might have higher oxidation states and/or be a weak Lewis base, as with nitro and imide compounds.  Amines can be primary, where the N atom is bound to one carbon (C-NH2); secondary, where the N atom is bound to two carbons (C-NH-C); or tertiary, where the N atom is bound to three carbons (C-(N-C)-C).  Amines can be aliphatic or aromatic.  It is also possible to bind a fourth group to the N atom, forming in this case a quaternary ammonium salt.  Amines are basic compounds (Lewis bases) that generally react as nucleophiles.

Unit 5 Time Advisory
This unit will take you 11.75 hours to complete.

☐    Subunit 5.1: 2.5 hours

☐    Subunit 5.2: 3.25 hours ☐    Subunit 5.3: 6 hours

☐    Sub-subunit 5.3.1: 4 hours

☐    Sub-subunit 5.3.2: 2 hours

Unit5 Learning Outcomes
Upon successful completion of this unit, the student will be able to:
- Derive the name of amines from their molecular structure, and vice versa. - Describe the difference among 1º, 2º, 3º amines and quaternary salts. - Describe the properties of amines in terms of hydrogen bonding, boiling points, basicity, and acidity. - Describe different methods of preparing amines. - Explain the mechanism of reactions involving amines as reagents.

5.1 Nomenclature, Structural, and Physical Properties   - Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Introduction to Amines (1)” Link:  YouTube: Freelanceteach’s “Organic Chemistry: Introduction to Amines (1)” (YouTube)

 Instructions: Please click on the link above, and watchthis video
(\#1) in its entirety (11:00 minutes) to for an introduction to the
nomenclature of 1º, 2 º, and 3 ºamines.  
    
 Viewing this lecture and pausing to take notes should take
approximately 15 minutes to complete.  

 Terms of Use: Please respect the copyright and terms of use
displayed on the webpage above.
  • Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Introduction to Amines (2);” “Organic Chemistry: Introduction to Amines (3);” and “Organic Chemistry: Introduction to Amines (4)” Links: YouTube: Freelanceteach’s “Organic Chemistry: Introduction to Amines (2);” (YouTube) “Organic Chemistry: Introduction to Amines (3);” (YouTube) and “Organic Chemistry: Introduction to Amines (4)” (YouTube)
     
    Instructions: Please note that these video lectures are optional.  For more explanation on the properties of amines, you may choose to click on the links above and watch lectures 2-4.  These videos run 11 minutes, 8 minutes, and 9 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: “Amines” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry:Amines” (HTML)

    Instructions: Please click on the link above, and read the sections titled “Nomenclature and Structure of Amines,” "Amines," and "Properties of Amines."  You will learn to recognize the name and structure and to predict the properties of amines.

    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.  

  • Lecture: Khan Academy’s “Amine Naming Introduction” and “Amine Naming 2” Link: Khan Academy's “Amine Naming Introduction” (YouTube) and “Amine Naming 2” (YouTube)

    Instructions: Please click on the links above, and watch the two video lectures to reinforce the material covered in the reading. 

    Viewing these lectures and pausing to take notes should take approximately 15-20 minutes to complete.

    Terms of Use: These videos are licensed under a Creative Commons Attribution-NonCommercial-NoDerives United States License 3.0.  They are attributed to the Khan Academy. 

  • Web Media: YouTube: Freelanceteach’s “Tutorial on Basicity of Aliphatic and Aromatic Amines” Link: YouTube: Freelanceteach’s “Tutorial on Basicity of Aliphatic and Aromatic Amines” (YouTube)

    Instructions:  Please click on the link above, and watch this entire lecture (10:22 minutes).  In this video presentation you will learn about naturally occurring nitrogen-based compounds.

    Viewing this lecture and pausing to take notes should take approximately 15 minutes to complete.
     
    Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.    

5.2 Synthesis of Amines   5.2.1 Preparation of 1º-Amines   - Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Introduction to Amines (5)” Link: YouTube: Freelanceteach’s “Organic Chemistry: Introduction to Amines (5)" (YouTube)

 Instructions: Please click on the link above, and watch this video
(\#5) in its entirety (9:54 minutes) to learn about the synthesis of
primary amines via the SN2 reaction.  

 Viewing this lecture and pausing to take notes should take
approximately 15 minutes to complete.  
    
 Terms of Use: Please respect the copyright and terms of use
displayed on the webpage above. 
  • Web Media: YouTube: Freelanceteach’s “Organic Chemistry: Introduction to Amines (6);” “Organic Chemistry: Introduction to Amines (7);” “Organic Chemistry: Introduction to Amines (8);” “Organic Chemistry: Introduction to Amines (9);” “Organic Chemistry: Introduction to Amines (10);” and “Organic Chemistry: Introduction to Amines (11)” Links: YouTube: Freelanceteach’s  “Organic Chemistry: Introduction to Amines (6);” “Organic Chemistry: Introduction to Amines (7);” “Organic Chemistry: Introduction to Amines (8);” “Organic Chemistry: Introduction to Amines (9);” “Organic Chemistry: Introduction to Amines (10);” and “Organic Chemistry: Introduction to Amines (11)” (YouTube)
     
    Instructions: Please note that these video lectures are optional.  For more explanation on the preparation methods of amines, you may choose to click on the links above and watch the videos for lectures 6-11.  The run times for these videos vary from 5 minutes to 11 minutes. This material is not required for successful completion of the course.
     
    Viewing these optional lectures should take approximately 1 hour to complete.
     
    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: “Preparation of 1º-Amines" Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry:Preparation of 1º-Amines" (HTML)

    Instructions: Please click on the link above, and read the sections relative to the synthesis of 1º-Amines.  Recall that primary amines are those amines with a nitrogen attached to two hydrogen and to an alkyl group.  Ammonia can undergo alkylation with alkyl halides to produce primary amines.  However, primary amines can be produced in two step process.  Primary amines produced in this alternate fashion are purer and produced in higher percent yield.  Read on to learn how to produce primary amines with the use of a nitrogen nucleophile and a carbon electrophile.  This resource also covers subunit 5.2.

    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.  

5.2.2 Preparation of 2º and 3º-Amines   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Preparation of 2º & 3º-Amines" Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Preparation of 2º & 3º-Amines" (HTML)

 Instructions: Please click on the link above, and read the sections
relative to the synthesis of 2º & 3º-Amines.  You will learn about
three methods of preparing secondary and tertiary amines.  

 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.  

5.3 Reactivity   5.3.1 Reactions of Amines   - Reading: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Reactions of Amines" and "Reactions of Amines (Continued)" Links: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Reactions of Amines" (HTML) and "Reactions of Amines (Continued)" (HTML)

 Instructions: Please click on the first link above.  On the webpage
“Reactions of Amines,” read the section titled “Amine Reactions.”
 Then, click on the “Reactions of Amines (Continued)” link above to
continue reading the rest of the chapter.  Ammonia and amines react
as nucleophiles when reacted with electrophiles to form various
products.  These readings will cover electrophilic substitution at
the nitrogen of amines.  This resource covers subunit 5.3, as well
as sub-subunits 5.3.1 and 5.3.2.   

 Reading and taking notes should take approximately 2 hours to
complete.  

 Terms of Use: Please respect the copyright and terms of use
displayed on the webpages above.  
  • Lecture: Khan Academy’s “Amine as a Nucleophile in Sn2 Reaction,” “Amine in Sn2 Part 2,” and “Sn1 Amine Reaction” Links: Khan Academy’s “Amine as a Nucleophile in Sn2 Reaction,” (YouTube) “Amine in Sn2 Part 2,” (YouTube) and “Sn1 Amine Reaction” (YouTube)

    Instructions: Please click on the links above, and watch the three video lectures to reinforce the material covered in the reading.  You will learn more about SN1 amine reactions and reactions involving amines as nucleophiles in SN2 reactions.  This resource covers subunit 5.3 as well as sub-subunits 5.3.1 and 5.3.2. 

    Viewing these lectures and pausing to take notes should take approximately 45 minutes to complete.

    Terms of Use: These videos are licensed under a Creative Commons Attribution-NonCommercial-NoDerives United States License 3.0.  They are attributed to the Khan Academy. 

  • Web Media: YouTube: Your Formula Sheet’s “Tutorial on Hofmann Elimination - Cope Elimination Part 1” and “Tutorial on Hoffmann Elimination - Cope Elimination Part 2” Links: YouTube: Your Formula Sheet’s “Tutorial on Hofmann Elimination - Cope Elimination Part 1” (YouTube) and “Tutorial on Hoffmann Elimination - Cope Elimination Part 2” (YouTube)

    Instructions:  Please click on the links above, and watch these tutorial videos (each are about 4 minutes) on the Hoffmanand CopeEliminationReactions. In these reaction types one or more beta-hydrogens must be on the alkyl group attached to the nitrogen.  Beta-hydrogen is eliminated and the end result is a double bond. This resource covers subunits 5.3, 5.3.1, and 5.3.2.

    Viewing these lectures and pausing to take notes should take approximately 15 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 Aryl Diazonium Salts” Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Reactions of Aryl Diazonium Salts" (HTML)
     
    Instructions: Please click on the link above, and read the entire section titled “Reactions of Aryl Diazonium Salts.”  Aryl diazonium salts are intermediates in substitution reactions where nitrogen is given off. The stability of the nitrogen molecule being given off helps drive the reaction.  A wide variety of substitution products can be produced depending on the reaction conditions and reactants.  In this lesson, you will learn about the Sandmeyer reaction and other important reactions where aryl diazonium salts act intermediates.  

    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.

5.3.2 Practice Problem Solving – Amines   - Assessment: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Practice Problems" and "Practice Problems" Web Media: Link: Michigan State University: Professor William Reusch’s Virtual Textbook of Organic Chemistry: "Practice Problems" (HTML) and "Practice Problems" (HTML)

 Instructions: Please complete this assessment after working through
the entirety of Unit 5.  Choose a practice problem set from the
scroll down menu on each webpage, and practice on the topic you
want/need.  These practice problems will reinforce what you have
learned in this unit about amine nomenclature, synthesis, and
reactions.  
    
 You should dedicate approximately 2 hours to practicing these
problem sets.  

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