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Organic Chemistry Chapters 1 and 2

by: Jayda Abrams

Organic Chemistry Chapters 1 and 2 Chem301

Marketplace > Virginia Commonwealth University > Chemistry > Chem301 > Organic Chemistry Chapters 1 and 2
Jayda Abrams
Virginia Commonwealth University
GPA 3.52

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These notes cover material taught by Jon Baker's organic chemistry one class. These notes also corrispond with the Organic Chemistry 8th Edition textbook by Wade. Topics include resonance, differen...
Organic Chemistry 1
Mr. Jon Baker
MCAT Organic Chemistry, Organic Chemistry, Organic Chemistry Lab
75 ?




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This 7 page Bundle was uploaded by Jayda Abrams on Tuesday August 30, 2016. The Bundle belongs to Chem301 at Virginia Commonwealth University taught by Mr. Jon Baker in Fall 2015. Since its upload, it has received 27 views. For similar materials see Organic Chemistry 1 in Chemistry at Virginia Commonwealth University.


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Date Created: 08/30/16
Resonance Compounds can have more than one Lewis structure that represents them correctly. The biggest difference between structures are where the electrons are placed in each one. These are called resonance structures or resonance forms. They are not different compounds but they are drawn in different ways. Resonance molecules will usually show characteristics of the different resonance structures even though it is something completely different. The actual molecule will be a resonance hybrid of the resonance forms. Since the actual molecule is a hybrid, this means the individual resonance structures are not completely accurate, and are not real. This can be compared to a rhino. The hybridization (or coming together) of a dragon and a unicorn will create a rhino. Even though dragons are not real, and unicorns are not real, rhinos are. This is the same in resonance. One structure that is not real combines with another structure that is not real and it creates a real structure. When comparing resonance forms, the more stable form is the major contributor and the less stable form is the minor contributor. Using Arrows in Resonance When drawing resonance structures arrows are very important. When showing the flow of electrons curved arrows are used. When showing the flow of a single electron a curved fishhook arrow is used. When showing that two structures have resonance a double sided arrow is used. Do not use a single sided arrow because this means that the two structures are in equilibrium! Flow of Electrons Flow of Electron Resonance Remember With Resonance… … ALL structures must be VALID Lewis structures. …you want to have as many octets as possible. …only electrons are moving between structures. Nuclei cannot be moved and bond angles stay the same! Also remember that the number of unpaired electrons as well as the formal charge will stay the same. …the most stable compounds have no unpaired electrons. …the major contributor is the one with the lowest energy. Good contributors usually have octets filled, have as many bonds as possible and have little charge separation. …negative charges are more stable on more electronegative atoms (like O, N and S). …resonance stabilization is important when it is used to delocalize a charge over two or more atoms. …curved arrows are used to show the flow of electrons. This diagram shows six different resonance structures of the same molecule. Notice how each individual structure has the same components and has the same total formal charge. Also notice the double headed arrow between structures and that the overall structure of the molecule has not changed. Chapter 1 The Basic Formulas Formula Description Example Shows which atoms are bonded to which. There Structural Formula are two types of Structural Formulas. There are Lewis Structures and there are Condensed Structural Formulas. Written without bonds and has the central atoms Condensed Structural and the atoms attached to Formula it listed out beside it. Nonbonding electrons are rarely shown. Show individual bonds Lewis Structures and often also shows the physical electrons. Also referred to as stick figure or skeletal structures. Bonds are represented by lines and carbons are assumed at Line Angle Formula the ends, and bends. Hydrogen atoms are usually not shown and it is assumed that carbon atoms have enough hydrogen atoms to give it a total of four bonds. Gives the number of Molecular Formula atoms of each element in a C 6 O12 6 molecule of a compound. Empirical Formula Compares the ratios of elements present. C 2 5 Chapter 2 Intermolecular Forces A molecular dipole moment is the dipole moment of the molecule taken as a whole. It is a good measure of a molecules overall polarity. Bond polarities can range from nonpolar to ionic. The polarity of an individual bond is measured as its bond dipole moment. When two molecules come close to each other they either attract or repel each other. The 3 major kinds of attractive forces that cause molecules to associate into solids and liquids are: 1. Dipole Dipole forces, 2. London Dispersion Forces and 3. Hydrogen bonds. Dipole Dipole Forces: An intermolecular force resulting from the attraction of one positive end and one negative ends of dipole moments on polar molecules. Dipole Dipole interaction only occur with two polar molecules and can occur with molecules that have hydrogen in them, but do not have hydrogen bonds (ex: HCl). London Dispersion Forces: An intermolecular force that attracts nonpolar molecules. London Dispersion Forces are a type of Van Der Wal Force and the attraction of two molecules occurs when two molecules have temporary dipole moments. Hydrogen Bonding: Hydrogen bonding is not a true bond, and is essentially a strong dipole dipole interaction. A bond is considered to be a hydrogen bond if there is a hydrogen bonded to a Nitrogen, Fluorine or Oxygen. These elements are extremely electronegative and will give hydrogen a positive charge. Even though hydrogen bonding is strong it is not as strong as covalent bonding. Summary of Hybridization and Molecular Geometry: Hybrid Orbitals Hybridization Geometry Approximate Bond Angle 2 s+p=sp Linear 180˚ ???? 3 s+p+p=s???? Trigonal 120˚ 4 s+p+p+p=s???? ???? Tetrahedral 109.5˚ 3 Bicyclic Molecules How Bicyclic Molecules and The Human Body are Similar! Two or more rings can be joined together into bicyclic or polycyclic systems. There are three ways two rings can be joined. They can be fused, bridged or spiro. The combination of two things coming together creating a system is like the human body because the human body has several parts that are put together to make a system. The two rings will touch at a carbon and the number of carbons touching defines the bicyclic as fused, bridged or spiro. The most common form is fused. Bridges is the second most common and spiro is very very rare. Definitions: Spirocyclic Compounds- When two rings share only ONE carbon atom. Bridged Rings- When two rings share TWO carbon atoms that are not adjacent to each other. Fused Rings- When two rings share TWO or more carbon atoms that are adjacent to each other. How many carbons shared between two rings can be remembered with the human body and specific body parts. 1. Skull starts with S and so does Spiro. The human body only has one skull and spirocyclic compounds only share one carbon. 2. Fused starts with F and does fingers. The human body has at least two fingers and fingers are side by side. Fused has at least two carbons with the carbons side by side. It is important to remember that to be fused the carbons must be adjacent. 3. Bridged starts with B and so does Bones. The human body has 2+ bones and they are not all side by side. Like bones in the body bridge rings have two carbons being shared but they are not side by side.


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