Lecture 12 - Lewis Structures II

Tuesday, February 20, 2024

1:30 PM

"The nature of the chemical bond is the problem at the heart of all chemistry." - ﷟HYPERLINK "https://www.nobelprize.org/prizes/chemistry/1954/ceremony-speech/"Linus Pauling Class notes for Lecture 1-11: https://bricejurban.github.io/CHEM111/ Assignments this week: ﷟HYPERLINK "https://boisestatecanvas.instructure.com/courses/28699/assignments/998317"HW 6 - Periodic Trends and Ionic Bonding (Fri 2/23) ﷟HYPERLINK "https://boisestatecanvas.instructure.com/courses/28699/assignments/998318"HW 7 - Lewis Structures (Mon 2/26) Reading for today's lecture: Chapter 7.5-7.10 Reading for next lecture: Chapter 8 Assignments next week: ﷟HYPERLINK "https://boisestatecanvas.instructure.com/courses/28699/assignments/945547"Midterm 2 (Tuesday (2/27) in-class) ﷟HYPERLINK "https://boisestatecanvas.instructure.com/courses/28699/assignments/993257"Emerging Tech in Chemistry (Friday (3/1) w/ replies by Sunday (3/3) Office Hours: Friday 11-1 CIC ﷟HYPERLINK "https://calendly.com/bricejurban/office-hours"By appointment Today (2/20) Lewis Structures Formal Charges Not enough electrons Too many electrons Resonance Structures End of content Midterm 2 Thursday (2/22) Valence Shell Electron Pair Repulsion Theory of Molecular Geometry (VSEPR) Drawing Covalent Molecular Structures (Lewis Structures) Algorithm for Drawing Lewis Structures Arrange the symbols of the atoms that are bonded together in the molecule next to one another. Compute the total number of valence electrons in the molecule by adding the number of valence electrons for all the atoms in the molecule. If the species is an ion rather than a molecule, then you must take the charge of the ion into account by adding electrons if it is a negative ion or subtracting electrons if it is a positive ion Represent a two-electron covalent bond by placing a line between the atoms that are assumed to be bonded to each other Arrange the remaining valence electrons as lone pairs about each atom so that the octet rule is satisfied for each one Check the formal charge on each atom to help with competing structures If there is not enough electrons, you may need to use double bonds, triple bonds or rings or the central atom(s) has a deficient octet or you have a radical If there are too many electrons, you may need to put electron pairs on the central atom and/or form double bonds to reduce formal charges (this will not be assessed in CHEM 101) Tips: The central atom is usually the least electronegative unless hydrogen which is always terminal. Some compounds will not have a central atom, but several. Be, B, and Al have deficient octets Elements in the 3rd row (S, P . . . )can expand their octet to have 10, 12, or more e-. If the molecule is an ion, bracket the structure and put a charge in the corner Molecules with an odd number of electrons will form a free radical, a reactive species.
If there are too many electrons, you may need to put electron pairs on the central atom and/or form double bonds to reduce formal charges (this will not be assessed in CHEM 101) Draw any valid resonance structures if requested Assigning Formal Charges help with determining the best structure (Step 5) Sometimes more than one possible structure may be possible. In that case it is necessary to assign a formal charge to the atoms in the structure to help aid us in choosing the correct one. We assume each pair of shared electrons are shared equally and assign one of the electrons to each atom. Lone electron pairs are assigned to the atom they are located on. Use this equation: Untitled picture.png Machine generated alternative text: formal charge on an atom In a Lewis formula total number of — valence electrons — in the free atom total number of lone-pair electrons total number of bonds Which structure is preferable for hydroxylamine? NH3O No formal charges (best structure) NH2OH Which structure is preferable for hydrogen peroxide? H2OO HOOH Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings
When there are not enough electrons (Step 6) Some elements are electron deficient are do not require an octet when forming a covalent bond. This is restricted to H, Li, Mg, Be, B, and Al. What is more likely is that you need to use double or triple bonds, especially if there is C or O present. If the molecule is larger, you can also form ring structures to use up 2 electrons. Lastly, if you have an odd number of electrons radical (unpaired electron) compounds are also possible. H2 Li2 BeCl2 MgH2 BH3 AlBr3 Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings
CO2 N2 HCN C2H6 (ethane) C2H4 (ethene) C2H2 (ethyne) Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings
CH3• (methyl radical) •NO (nitric oxide) When there are too many electrons (Step 7) Some elements allow for an expanded octet when forming covalent bonds. This is restricted to elements in the third shell or higher including the elements: P, S, Cl, As, Se, Te, Br, I, and even Xe. Never will an element such as C, N, O, or F have an expanded octet  SF6 XeF2 IF5 Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings
 SF6                 XeF2 IF5 When resonance structures are needed (Step 8) Resonance refers to areas in the molecule where the electrons in double/triple bonds are delocalized across more than two atoms. Especially for polyatomic ions and organic molecules, multiple structures can be needed to fully capture the molecule's complexity. A double headed arrow is used to indicate a resonance structure ↔. Molecules do not transition between resonance structures but exist as them all simultaneously. They are the closest approximation we can get to representing the molecule. HCO3– (hydrogen carbonate)               Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings
  C2O42– (oxalate) Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings
C6H6 (benzene) (C6H5)3C• (trityl radical) First organic radical discovered. Moses Gomberg in 1900 at University of Michigan (my alma mater) Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings
6 other resonance structures are possible with the other two rings systems. This delocalization is what gives rise to the stability of the radical. Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings Ink Drawings

 

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