Chemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University1Chemistry 500: Chemistry in Modern LivingTopic 7: Manipulating Molecules and Designing DrugsOrganic ChemistryChemistry in Context, 2nd Edition: Chapter 11, Pages 351-386Chemistry in Context, 3rd Edition: Chapter 10, Pages 375-414Outline Notes by Dr. Allen D. Hunter, YSU Department ofChemistry, 2000.Chemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University2Outline7A ORGANIC CHEMISTRY.................................................................................................................................................37B HOW DO WE KNOW MOLECULAR STRUCTURES?.......................................................................................57C APPROACHES TO MAKING MOLECULES ..........................................................................................................97D STRUCTURAL ISOMERS............................................................................................................................................107E FUNCTIONAL GROUPS...............................................................................................................................................137F DRUG DISCOVERY........................................................................................................................................................20Chemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University37A Organic ChemistryØ Organic Chemistry is the study of the chemistry of carbonØ What makes carbon special?Ø Many bond typesØ Forms long chainsØ Forms strong bonds to almost all elementsØ Over 16,000,000 organic compounds knownØ Being discovered at the rate of over 1,000,000 per yearØ BondingØ Lewis dot structuresØ Remember from Topic 2 the ways that different elementsbondChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University4Ø Bond Distances and Bond AnglesØ Ethane, C2H6Ø Carbon - Carbon Single BondØ C-C distance of 1.54 •Ø Bond angles of 109.5 °Ø Ethene, C2H4Ø Carbon - Carbon Double BondØ C-C distance of 1.34 •Ø Bond angles of 120 °Ø Ethyne, C2H2Ø Carbon - Carbon Single BondØ C-C distance of 1.20 •Ø Bond angles of 180 °Chemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University57B How Do We Know Molecular Structures?Ø First ApproachØ Logical ReasoningØ Informed by reactivities and crude compositionsØ Only tools available were:Ø BalancesØ Melting Points, mpØ Boiling Points, bpØ Taste, Smell, Textures, etc.Chemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University6Ø Second ApproachØ Elemental AnalysisØ Classical Wet MethodsØ One element at a timeØ Example: Ag+ precipitation of Cl-Ø Instrumental MethodsØ Multi-element SimultaneousØ AutomatedØ Example: Combustion AnalysisChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University7Ø Third ApproachØ X-Ray DiffractionØ What is a crystal?Ø What is an X-ray?Ø What are the components of a diffractometer?Ø How does one solve a structure?Ø Types and Reliability of InformationChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University8Ø Fourth ApproachØ Sporting MethodsØ The specific absorption of electromagnetic wavesØ The pattern of the absorption tells us information aboutthe structure (indirectly)Ø Infrared Spectroscopy, IRØ Ultraviolet-Visible Spectroscopy, UV-VisØ Nuclear Magnetic Resonance Spectroscopy, NMRØ Mass Spectroscopy, MSChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University97C Approaches to Making MoleculesØ Synthetic Methods DevelopmentØ Conventional Serial Synthesis MethodsØ Combinatorial Synthesis MethodsChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University107D Structural IsomersØ DefinitionØ Same atoms but attached differentlyØ TypesØ Positions of AtomsØ Strait Chain vs. Branched ChainØ Multiple Bonds vs. RingsØ Example [For the following molecular formulae, draw all of the structuralisomers (up to a maximum of 5). Be sure that you show all atoms and bonds foreach.]Ø C2H6OChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University11Ø Ask Students: For each of the following molecules, drawall structural isomers (up to a maximum of five)Ø Group ActivityØ C2H6O2Ø C3H9NChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University12Ø C4H10Ø C3H6Chemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University137E Functional GroupsØ Graphics from Text: Figure 11.2 in 2nd Edition and 10.2 in 3rdEdition, Functional Group ClassificationØ HydrocarbonsØ AlkanesØ AlkenesChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University14Ø AlkynesØ ArenesChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University15Ø Groups with Oxygen(s)Ø AlcoholsØ EthersØ AldehydesChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University16Ø KetonesØ Carboxylic AcidsØ EstersChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University17Ø Groups with NitrogenØ AminesØ AmidesChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University18Ø Ask Students: In the following molecule(s), identify allfunctional groups by circling then and then name eachfunctional groupØ Group ActivityH CHHC CH HCOOCH HCOH HCCHCCCCCCNCCCCCOOHHHHHHH HHHH HHHCOCCCOHCCCCOOCHHHH HHHHHHHHHHChemistry 500 Dr. Hunter’s Class Topic 7.2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State