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Module 1: Anatomy of Organic Molecules

Learning outcomes. You should be able to….


• Quickly and correctly convert Lewis structures to line-diagrams & visa versa (a.k.a
Drawing Organic Molecules)
• Quickly determine the Formal Charge on an atom given the Lewis structure & visa
versa
• Quickly identify the Hybridization of an atom in an organic molecule and describe the
geometry around that atom and bonding (s and p bonding).
• Be able to recognize and draw resonance structures
• Quickly identify and name Functional Groups in an organic molecule
• Understand Intermolecular Forces and use these concepts to predict physical
properties of organic molecules
• Know arrow formalism (the use of arrows in organic chemistry)

To aid you in achieving these learning outcomes short videos on many of these topics are
posted under under Course Modules on OWL.
Lewis Structures and Converting to Line Diagrams:
Convert this to a line diagram
Hybridization: Structure and Shape of Organic Molecules (pgs 13-16)
Label Hybridization of EACH atom:
Label Hybridization of EACH atom:
Are there exceptions to the general approach?
Yes…the most common one we will see is:
lone pairs adjacent to p bonds

Because the lone pairs


are conjugated, in
resonance with the pi
bond, the geometry is
better described as
planar- which is sp2
Are there exceptions to the general approach?

lone pairs adjacent to p bonds: Example amides

Because the lone pairs


are conjugated, in
resonance with the pi
bond, the geometry is
better described as
planar- which is sp2

N is best described as sp2 hybridized


Formal Charges: pgs 9-13 in Brown
What is the hybridization of each of the following?
You should be able to go the other way too!
Resonance: Section 1.5, pgs 18-21

O
Not all arrow pushing is correct!
Summary of Patterns for drawing resonance structures:
What is the hybridization of the indicated atoms in carfentanil?

O O
O

N
N

Carfentanil: derivative of fentanyl that is 100 times more potent


5000 times more potent than heroin and 10,000 x than morphine
Module 1: Anatomy of Organic Molecules

Learning outcomes. We have reviewed


• Quickly and correctly convert Lewis structures to line-diagrams & visa versa (a.k.a
Drawing Organic Molecules)
• Quickly determine the Formal Charge on an atom given the Lewis structure & visa
versa
• Quickly identify the Hybridization of an atom in an organic molecule and describe the
geometry around that atom and bonding (s and p bonding).
• Be able to recognize and draw resonance structures
You are responsible for knowing:
• Quickly identify and name Functional Groups in an organic molecule
• Understand Intermolecular Forces and use these concepts to predict physical
properties of organic molecules
• Know arrow formalism (the use of arrows in organic chemistry)

To aid you in achieving these learning outcomes short videos on many of these topics are
posted under under Course Modules on OWL.
Topic Summary
• Textbook sections covered: all of Chapter 1
• Suggested Quick Quiz questions from Chapter 1: all
• Suggested problems from the end of Chapter 1: 21-32, 34, 37, 38, 40-43, 47-
52, 53-56, 62, 63, 65, 67, 68
• On-line (WileyPlus/Orion) exercises are also available

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