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Organic Chemistry

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Published in: Chemistry
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what is organic chemistry and what are organic compounds

Shilpi M / Rajkot

4 years of teaching experience

Qualification: M.Sc, MBA

Teaches: Chemistry

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  1. k estradiol N-CH3 OH CH3/ testosterone H3C. O. N w morphine -CH3 00 ACAO* heroin codeine Universe Subtleties in Structure N -CH3 i;: Other .3Ar P Li Si Mg Na Ne jo c o He uH Crustal Rock Sea Human Life is Based on Or anic Com 100% 90% Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. ounds 5
  2. 30% 10% 00/0 Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 6
  3. How: Structure and Reactivit Structure - what atoms are present & how they are bonded together Reactivity - potential of structure to undergo chemical change If likely - reactive (unstable) If unlikely - unreactive (stable) Potential Energy: function of position or configuration of components Potential Ener Structure Reactivity if low, compound more stable, change less likely if high, compound less stable, change more likely Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. Structure Foundation of organic chemistry 1. 2. What atoms (besides carbon) are important? How are these atoms bonded together? Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 7
  4. 100% If-l- 40% 00/0 crude petroleum dry nonvascular plant tissue dry vascular plant tissue dry h muscl man issue (HO . Other Na c Body C (H20 65% mass) Structure - Atoms of Organic Molecules Food we eat, fragrances we smell, colors we see, clothes we wear Typical drug contains 20-80 atoms (C, H, N, O, F, S, P, Cl, Br, l) Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. Main Atoms in Organic Chemistry Na Mg K Ca sc TiVCr Mn Fe co Ni cu As Se Br Rbl [Sr] [Y] [Zr] [Nib Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. Ne 8
  5. Electron configuration: number and arrangement of electrons about an atom Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 9
  6. Electron Configuration of Main Atoms round State Element H Be B c N o F Ne M Si p s Ar onfi uration Isl 1s2 1s22sl 1s22s2 1S22S22 1 Is s 2 3 1s22s22 1s22s22 1 s22s22 1s22s22 1 s22s22 1s22s22 1 s22s22 1s22s22 122 1s22s22 122 1 S22S22 122 S23 1 s23 3 S23 5 Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. Electron Confi uration and Valence Electrons Electron redistribution (change in configuration) is the origin of chemical change WHY? Attain lower ENERGY (achieved when outer shell is filled - 8 electrons) Process of chemical bonding: adding or taking away outer shell electrons to gain a closed shell configuration How do atoms maintain 8 electrons as well as participate in chemical bonding? 10
  7. Bonding Possibilities of Main Organic Atoms Each atom has a limited number of possibilities to satisfy octet: 1. Nonbonding (electron pair localized on one atom) 2. Bonding (electron pair shared between two atoms) a. Single bond (1 shared pair) b. Double bond (2 shared pairs) c. Triple bond (3 shared pairs) H-C-N-H methyl amine H-C-C'. o-H 1 HO. • acetic acid — 40 ZN acetonitrile (H is exception to octet rule - has 1 electron) Electron Pair Domain - region of high valence shell electron density (bonding or nonbonding) Bonding Patterns: Formal Charge O # Electron Pair Domains 4 3 2 1 Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 11
  8. # Electron Domains Courtesy of Jeffre Used with permiss bana-Champaign. Bonding Patterns: Formal Charge +1 Bonding Patterns: Formal Charge -1 # Electron Domains Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 12
  9. Boron Electron configuration S B. ecial reactivit Neutral, but electron deficient can tolerate an incomplete octet better than any other atom in the second row Octet, but charged EN = 2, least suited of all second row elements to carry a negative charge Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. Organic Structures: Summa V Organic Chemistry v Relationship of Structure, Energy, and Reactivity Structure V V Atoms Bonding V How/Why Atoms Bond Together V Bonding Patterns Representing molecules V Lewis and Kekule Structures o Line-angle Formula 0 3-D o Orbital Drawings Functional Groups Resonance Lewis Structure HHI H-C-C-O-HI yJKekule Structurej 13
  10. Re resentin Molecules: Line-An le Formula H -N -C -C-O: H. H' H-C-H h Tyrosine O OH OH H Iodomethane HO Estradiol OH Cl-13 le Formulas Rules of Drawing Line-An Bonds are represented by lines Assume carbon atoms at the ends of lines and where they meet Assume enough C-H bonds to give each carbon atom four bonds (octet) Carbon and hydrogen atoms are only drawn at termini for aesthetics Draw heteroatoms and attached hydrogen atoms (N, O, P, Cl, Br, F, l, etc. >(any atom that is not carbon) x H JEH C' HO' CH3 Incorrect! (Why?) H3CACH3 Don't forget about the implied hydrogen atoms! Always show all Ione pairs! (helps with electron bookkeeping) 14
  11. Re resentin Molecules: 3-D Lewis/Kekule and Line-Angle structures don't tell the whole story! Molecules are not flat - use dashes and wedges to show 3-D image Governed by VSEPR Line - in plane of paper Dash - going into the paper Wedge - coming out of the paper I-I-dh-l HsS H H CH3 H3C H CH3 Same atoms, different spatial arrangement Representing Molecules: Orbital Drawings I Atomic Orbita 2px orbital 2P orbital node 2s atomic orbital 2pz orbital 15
  12. Re resentin Molecules: Orbital Drawin s Il H brid Orbitals Representing Molecules: Orbital Drawings sp2 1200 sp2 electron density distributed to the corners of a triangle (trigonal planar) Ethylene XC=C bond G bond 109.50 sp3 electron density distributed to the corners of a tetrahedron 1 800 sp sp sp electron density distributed linearly pi orbital network Acetylene H-C so -H 16
  13. Functional Groups The atoms of organic molecules exist in common combinations Each combination: > unique chemical properties and reactivity > behaves similarly in every organic molecule 10 million organic compounds exist! Predict how any one of those compounds reacts by analyzing its "functional groups" Functional Group - group of atoms with characteristic chemical behavior no matter what molecule it's in Chemistry of every organic molecule, regardless of size or complexity, governed by functional groups Functional Groups to Learn Nitrogen-Containing Sulfur-Containing Hydrocarbons Oxygen-Containing alkyne diene arene Halogen-Containing alcohol phenol ether epoxide ketone aldehyde 0.4 0 0 rr 101 c-c-c— il amine nitrile nitro imine o- o sulfide thiol sulfoxide sulfone thioester Carboxylic Acid Derivatives c -s-c— 10 0 11 02+1 c-s-c— 10 11 alkyl halide aryl halide carboxylic acid halide Carboxylic acid anhvdride ester amide 10 -c-c -x 1 carboxylic cr acid
  14. On to Resonance ... U/ Organic Chemistry ./ Relationship of Structure, Energy, and Reactivity Structure U/ Atoms s/ Bonding u/ How/Why Atoms Bond Together v/ Bonding Patterns •/ Representing molecules n/ Lewis and Kekule Structures v/ Line-angle Formula v/ 3-D Orbital Drawings M/ Functional Groups Resonance Resonance IF YOU DO NOT UNDERSTAND RESONANCE, YOU WILL NOT PASS 5.12! Resonance is like riding a bike. Once you learn, you never forget .. 18
  15. hen one Lewis structure •ust isn't enou h. Lewis structure or H3N 2 = 24 valence e- Resonance contributor Resonance contributor 0* o 'n* Resonance Hybrid Electrons are DELOCALIZED A molecule can't always be accurately represented by one Lewis structure These molecules are weighted average, or hybrids, of two or more Lewis structures (electrons do not move to either one of the oxygen atoms or the other) A Resonance Metaphor Figure removed due to copyright reasons. 19
  16. Wh is Resonance So Very 1m ortant? >95% of the reactions in 5.12 occur because of the attraction of one molecule containing a region of high electron density to a second molecule containing a region of low electron density oo oo To predict how and when two molecules will react, need to be able to predict the regions of low and high electron density 5 'OANA>O.• *O 5 o 5 Resonance hybrid O N O (lone pairs not depicted in resonance hybrids) Tracking Changes in e Configuration Need a way to keep track of the changes in electron O •Q •o Curved Arrow Notation configuration between resonance contributors Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 20

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