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Organic Chem 1

by: Tiara Butler

Organic Chem 1 Chem 2100

Tiara Butler
GPA 3.2

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About this Document

These notes covered what was on exam 1. This information will need to be known for the final.
Organic Chemistry 1
John McCormick
Class Notes
Chemistry, organic, Exam 1
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This 2 page Class Notes was uploaded by Tiara Butler on Saturday April 9, 2016. The Class Notes belongs to Chem 2100 at University of Missouri - Columbia taught by John McCormick in Spring 2016. Since its upload, it has received 15 views. For similar materials see Organic Chemistry 1 in Chemistry at University of Missouri - Columbia.


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Date Created: 04/09/16
O.Chem Chapter 2 Drawing Structures  When drawing an organic structure that shows all atoms and bonds, generally a line is used to  represent a shared pair electron in a bond; multiple bonds are shown by drawing 2 or 3 lines b/w the  atoms; unshared electrons are shown as dots  Condensed formulas commonly are used to represent organic structures more efficiently; some, most  or even all the bonds are left out  Bond­line formulas or carbon skeleton diagrams are the most common way to draw organic  structures; hydrogens bonded to carbon are not shown unless they have special relevance (same with  carbons); heteroatoms­ atoms other than carbons and hydrogen­ all are shown together w/ the  hydrogens that are bonded to them ­ Advantage: natural focus on the group of atoms of the molecule that have special chemical  reactivity; functional groups  Each carbon has 4 pairs of electrons associated with it; it’s 4 valence electrons + electrons associated with the atoms that are bonded to each carbon atom 3D Bond Line Structures  Bonds pointing away from the viewer (behind the plane of the paper) are shown using a dashed line;  bonds pointing toward the viewer (in front of the plane of paper) are shown using a wedge  Acrylic molecules (molecules that have no rings) and cyclic molecules Formal Charges on Carbon  When carbon has 8 electrons (filled outer shell) and all 4 pairs of electrons are shared, generally there  is not a charge on that carbon atom  When carbon has 8 electrons and only 3 pairs of electrons are shared, the 4  pair is a “lone pair”  (unshared); that carbon atom has a formal negative carbon ion called a carbanion (negative charge  results in an excess of electrons)  When carbon has only 6 electrons in its valence shell, 3 shared electron pairs, that carbon atom has a  formal positive charge; positive charge is called a carbocation (positive charge results from a  deficiency of electrons)  When carbon has 7 electron in its valence shell, 3 shared pairs of electrons and 1 unpaired electron  that is not shared, that carbon atom has no formal charge; this is called a carbon radical  Unshared Electron Pairs  In most stable, neutral organic molecules, heteroatoms have unshared electron pairs  There is no formal charge when  ­ N has 3 bonds and 1 unshared pair ­ O has 2 bonds and 2 unshared pairs ­ A halogen (F, Cl, Br, or I) has 1 bond and 3 unshared pairs  These heteroatoms have a negative charge when the # of bonds is decreased by 1 and the # of  unshared pairs increases by 1: ­ N has 2 bonds and 2 unshared pairs ­ O has 1 bind and 3 unshared pairs ­ A halogen is bonded to nothing and has 4 unshared pairs  These heteroatoms have a positive charge when the # of bonds is increased by 1 and the # of unshared pairs decreases by 1: ­ N has 4 bonds and no unshared pair ­ O has 3 bonds and 1 unshared pair ­ A halogen has 2 bonds and 2 unshared pairs Resonance and Curved Arrows  Structures that have different, reasonable arrangements of electrons for the exact same arrangement of atoms are termed “resonance structures”  Although resonance structures appear to be distinct and different, in actuality, individual resonance  structures do not exist 


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