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32 Pages

Chem1506.OutlineNotes.Section1

Course: CHEM 1506, Fall 2008
School: Youngstown
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1506 Dr. Chemistry Hunters Class Section 1 Notes - Page 1/32 Chemistry 1506: Allied Health Chemistry 2 Section 1: Structure and Bonding in Alkanes Basics of Structure and Bonding Outline SECTION SECTION SECTION SECTION SECTION SECTION SECTION SECTION SECTION SECTION 1.1 WHAT IS AN ORGANIC CHEMICAL?....................................................................................2 1.2 SOURCES OF ORGANIC...

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1506 Dr. Chemistry Hunters Class Section 1 Notes - Page 1/32 Chemistry 1506: Allied Health Chemistry 2 Section 1: Structure and Bonding in Alkanes Basics of Structure and Bonding Outline SECTION SECTION SECTION SECTION SECTION SECTION SECTION SECTION SECTION SECTION 1.1 WHAT IS AN ORGANIC CHEMICAL?....................................................................................2 1.2 SOURCES OF ORGANIC CARBONS .......................................................................................4 1.3 STRUCTURES AND BONDING ................................................................................................5 1.4 HYDROCARBONS AND ALKANES ......................................................................................16 1.5 IUPAC NOMENCLATURE ......................................................................................................20 1.6 CYCLOALKANES.....................................................................................................................23 1.7 PHYSICAL PROPERTIES .......................................................................................................24 1.8 CHEMICAL PROPERTIES......................................................................................................25 1.9 FUNCTIONAL GROUPS ..........................................................................................................26 1.10 AMINO ACIDS HAVING ALKYL SIDE CHAINS...............................................................29 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 2/32 Section 1.1 What is an Organic Chemical? Definition Compounds of Carbon Mostly Covalent Bonding Related to Molecules of Life Where do they come from? Numbers Total (> 10,000,000) Fully isolated, characterized, and reported New (> 1,000,000 / year) Accelerating rate of discovery Linear Synthetic Strategies vs. Combinatorial Synthetic Strategies Characterization Methods Automation and Productivity 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 3/32 What is so Special about Carbon? Bond Orders (single bonds, double bonds, and triple bonds) Strong Stable bonds to almost all atom types Long chains This is a unique combination 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 4/32 Section 1.2 Sources of Organic Carbons Nature and Organic Chemicals Isolation from natural sources natural products Synthesis and Organic Chemicals man made organic products lab scale synthesis vs. factory scale synthesis Production Choices from Dual sources Cost Considerations and environmental considerations Semi-Synthetic Organic Compounds 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 5/32 Section 1.3 Structures and Bonding How Do We Know Structures? Analytical Data Spectroscopic Methods Sporting Methods Specific absorption of light NMR = Nuclear Magnetic Resonance (cf. MRI, Magnetic Resonance Imaging) Infra-Red (IR) Ultra Violet-Visible (UV-Vis) 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 6/32 X-Ray Crystallography/Diffraction Non-Sporting Method Single Crystals Hardware Data Collection Data Analysis General Features of Structures Complex 3D Shapes 109.5, 120, and 180 Bond Angles C~C Distances: 1.2 1.55 Bond Distances for Hydrocarbons and 1.54 for Alkanes (and C-H 1 ) Structural Correlations with Properties 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 7/32 Molecular Formulae Elements present Number of atoms of each type Molecular Weight Not unique to molecules e.g. C11H14O 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 8/32 Structural Formulae Connectivity 3D Structures (unique) Related to Properties Mp, Bp, taste, toxicity, strength, etc. Examples a few pages on 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 9/32 Rationalization by Lewis, VSEPR, and VBT Theories Lewis Theory Review (section 3.6) Lone pairs and bonds Valence electrons Rigorous Method Count number of valence electrons Place total number of valence electrons around each atom to give it a complete octet 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 10/32 Quick and dirty Lewis method (for common "organic" elements) Bond Lengths Bond Angles H one bond and no lone pairs F, Cl, Br, and I one bond and three lone pairs O, S, Se, and Te two bonds and two lone pairs N, P, As, and Sb three bonds and one lone pair C, Si, Sn, and Ge four bonds and no lone pairs 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 11/32 VSEPR, Valence Shell Electron Pair Repulsion Theory, Review Molecular shapes bond angles Four groups Tetrahedral, td Three groups Trigonal planar Two groups Linear Number of "things" 4 things -> 109.5 3 things -> 120 2 things -> 180 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 12/32 Valence Bond Theory, VBT, Review Hybridization 109.5 -> sp3 120 -> sp2 180 -> sp 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 13/32 Examples of Problem Types Predict Lewis Structures Predict hybridizations Predict bond angles Predict bond lengths Worked Example(s) [For each of the following molecules, draw the correct Lewis structure and predict the hybridizations, bond lengths and bond angles around the * atoms.] 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 14/32 Structural Isomers Definition Same atoms but attached differently Types Positions of Atoms Strait Chain vs. Branched Chain Multiple Bonds vs. Rings Examples [For following molecular formulae, draw all of the structural isomers (up to a maximum of 5). Be sure that you show all atoms and bonds for each.] C2H6O 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 15/32 C4H10 C3H6 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 16/32 Section 1.4 Hydrocarbons and Alkanes Definitions Hydrocarbon (CnHm) sources Alkane (CnH2n+2, e.g., C2H6, C5H12, C100H202) only single bonds Alkene At least one double bond Alkyne At least one triple bond Aromatic/Arene "benzene like" "alternating" single and double bonds around a ring 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 17/32 Examples of Alkanes Methane (sources, cost), CH4 Ethane, C2H6 Propane, C3H8 Butane, C4H10 Know C1-C10 Alkane Names (See Table in Text) (Pent, Hex, Hept, Oct, Non, Dec) Molecular Weight -> Mp and Bp 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 18/32 Structures of Alkanes Bond angles ( 109.5) Bond distances ( 1.54 (C-C) and 1.0 (C-H)) Ring Strain (C3 and C4 rings) Types of Carbons in Alkanes 1, Primary Carbon, CH3 2, Secondary Carbon, CH2 3, Tertiary Carbon, CH 4, Quaternary Carbon, C Examples 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 19/32 Rotation Around Bonds in Alkanes -Bonds, Sigma-Bonds Free Rotation or Restricted Rotation? Steric Effects, Rings Alkane Structural Isomers e.g. C5 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 20/32 Section 1.5 IUPAC Nomenclature Steps Find longest continuous chain (Alkane) Number carbons in chain from end that give side chains lowest number Identify side chains Name Attachment Position(s) Number of groups (di, tri, tetra, penta, hexa, hepta, octa, nona, deca) Assemble name (punctuation) , - 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 21/32 Side Chain Names Alkyl (See Table in text for prefixes) Methyl, CH3 Ethyl (C2H5) CH2CH3 Propyl (C3H7) n-propyl iso-propyl Butyl (C4H9) n-butyl iso-butyl sec-butyl tert-butyl Pentyl, etc. 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 22/32 n-alkyl Iso-alkyl Halogens Fluoro Chloro Bromo Iodo Examples 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 23/32 Section 1.6 Cycloalkanes cyclo prefix cyclobutane, cyclohexane, etc. number from functional groups Ring strain (C3 & C4) Examples 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 24/32 Section 1.7 Physical Properties Physical State Mp and Bp Depends on MW Van der Waals Forces Intermolecular Bonding vs. Intramolecular Bonding Non-Polar compounds Definition of Polar vs. Non-Polar Solubility Non-polar organic solvents vs. water Density Cf. water 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 25/32 Section 1.8 Chemical Properties UNREACTIVE Combustion (balance reactions) __ CH4 + __ 2 __ C2 + __2 __ C3H6 + __ 2 __ C2 + __2 __ C6H6 + __ 2 __ C2 + __2 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 26/32 Section 1.9 Functional Groups Framework vs. Functional Group Identifying Functional Groups (See Table in text for Functional Groups) Alkene Alkyne Aromatic Alkyl Halide Alcohol 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 27/32 Ether Thiol (mercaptan) Amine Aldehyde Ketone 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 28/32 Carboxylic Acid Ester Amide 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 29/32 Section 1.10 Amino Acids Having Alkyl Side Chains Amino Acids (Building Blocks of Proteins) Generic AA = H2N-CHR-CO2H 6 Nonpolar Alkyl Side Chains Glycine, R = H Alanine, R = CH3, methyl Valine, R = CH(CH3)2, isopropyl Leucine, R = CH2CH(CH3)2, isobutyl Isoleucine, R = CH(CH3)(CH2CH3), sec-butyl Proline, HN{CH2CH2CH2-ring}CH-CO2H 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 30/32 Index of Topics and Vocabulary 109.5 ............................................................6, 11, 12 120 ...............................................................6, 11, 12 180 ...............................................................6, 11, 12 1 ............................................................................18 2 ............................................................................18 3 ............................................................................18 4 ............................................................................18 Alanine ....................................................................29 Alcohol ....................................................................26 Aldehyde..................................................................27 Alkane .....................................................................16 Alkane Names .........................................................17 Alkane Structural Isomers .......................................19 Alkanes ....................................................................17 Alkene ...............................................................16, 26 Alkyl........................................................................21 Alkyl Halide ............................................................26 Alkyne ...............................................................16, 26 Amide ......................................................................28 Amine ......................................................................27 Amino Acids............................................................29 Analytical Data ..........................................................5 Arene .......................................................................16 Aromatic ............................................................16, 26 Attachment Position(s) ............................................20 Automation ................................................................2 balance reactions......................................................25 benzene ....................................................................16 bond angles........................................................11, 13 Bond angles .............................................................18 Bond Angles ........................................................6, Bond 10 distances.........................................................18 Bond Distances ..........................................................6 bond lengths.............................................................13 Bond Lengths...........................................................10 Bond Orders...............................................................3 bonds .........................................................................9 Bp ..................................................................8, 17, 24 Branched Chain .......................................................14 Bromo ......................................................................22 Butane......................................................................17 Butyl ........................................................................21 C2H6 .........................................................................17 C3H8 .........................................................................17 C4H10........................................................................17 Carboxylic Acid.......................................................28 CH4 ..........................................................................17 Characterization Methods..........................................2 characterized..............................................................2 Chemical Properties.................................................25 Chloro......................................................................22 CnHm ........................................................................16 Combinatorial Synthetic Strategies ...........................2 Combustion..............................................................25 complete octet............................................................9 Compounds of Carbon...............................................2 Covalent Bonding ......................................................2 cyclo prefix..............................................................23 Cycloalkanes............................................................23 cyclobutane..............................................................23 cyclohexane .............................................................23 Dec...........................................................................17 deca..........................................................................20 Density.....................................................................24 di ............................................................................20 double bond .............................................................16 double bonds..............................................................3 Ester.........................................................................28 Ethane......................................................................17 Ether ........................................................................27 Ethyl ........................................................................21 factory scale synthesis ...............................................4 Fluoro ......................................................................22 Framework...............................................................26 Free Rotation ...........................................................19 Functional Groups .............................................26, 29 Generic AA..............................................................29 Glycine ....................................................................29 Halogens ..................................................................22 Hept .........................................................................17 hepta ........................................................................20 Hex ..........................................................................17 hexa .........................................................................20 hybridization............................................................13 Hybridization...........................................................12 Hydrocarbon ............................................................16 Hydrocarbons and Alkanes......................................16 Infra-Red....................................................................5 Intermolecular Bonding...........................................24 Intramolecular Bonding...........................................24 Iodo..........................................................................22 IR ..............................................................................5 Iso-alkyl...................................................................22 iso-butyl...................................................................21 Isoleucine.................................................................29 iso-propyl.................................................................21 IUPAC Nomenclature..............................................20 Ketone .....................................................................27 2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University Chemistry 1506 Dr. Hunters Class Section 1 Notes - Page 31/32 lab scale synthesis......................................................4 Leucine ....................................................................29 Lewis Structures ......................................................13 Lewis Theory.............................................................9 Linear.......................................................................11 Linear Synthetic Strategies ........................................2 lone pairs .................................................................10 Lone pairs ..................................................................9 Long chains ...............................................................3 longest continuous chain .........................................20 Magnetic Resonance Imaging....................................5 man made organic products .......................................4 mercaptan ................................................................27 Methane ...................................................................17 Methyl .....................................................................21 Molecular Formulae ..................................................7 Molecular Weight ................................................7, 17 Molecules of Life.......................................................2 Mp .................................................................8, 17, 24 MRI ...........................................................................5 Multiple Bonds ........................................................14 MW..........................................................................24 n-alkyl......................................................................22 natural products .........................................................4 n-butyl .....................................................................21 NMR..........................................................................5 Non ..........................................................................17 nona .........................................................................20 Non-Polar ................................................................24 Nonpolar Alkyl Side Chains....................................29 Non-Polar compounds .............................................24 n-propyl ...................................................................21 Nuclear Magnetic Resonance ....................................5 Number carbons in chain .........................................20 Number of "things ...................................................11 Number of groups....................................................20 Oct ...........................................................................17 octa ..........................................................................20 octet ...........................................................................9 Pent..........................................................................17 penta ........................................................................20 Pentyl.......................................................................22 Physical Properties ..................

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ARDENT AND WELL-MEANING JURISPRUDENCE WAYLAID I have only one statement that will ensure against profligy, especially in rural obbligato mode as one's own thunderstorm or hillside pasture, is simply then to have come in out of the rain, leave the mat
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CURRICULUM VITAEJIANZHEN YU Department of Chemistry, Hong Kong University of Science & Technology Clear Water Bay, Kowloon, Hong Kong Telephone: 852-2358-7389 Fax: 852-2358-1594 e-mail: chjianyu@ust.hk Academic Qualifications: B.S. M.S. 1989 1992 N
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