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Chapter 11 Alkenes, Alkynes, and Aromatic Compounds

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Chapter 11 Alkenes, Alkynes, and Aromatic Compounds

Chemistry 506 Dr. Hunter’s Class Chapter 11.1

    Chemistry 506: Allied Health Chemistry 2

    Chapter 11: Alkenes, Alkynes, and Aromatic Compounds

    Hydrocarbons with Multiple Bonds

    th Introduction to General, Organic & Biochemistry, 5 Edition by Bettelheim and March: Chapter 11, Pages 353-390

     Outline Notes by Dr. Allen D. Hunter, YSU Department of

    Chemistry, ?2000.

    Outline

11A SECTION(S) 11.1/2/4 INTRODUCTION AND NOMENCLATURE OF ALKENES................................................... 2

    11B SECTION(S) 11.3 -BONDS .......................................................................................................................................... 4 11C SECTION(S) 11.5 PHYSICAL PROPERTIES .............................................................................................................. 5 11D SECTION(S) 11.6 CHEMICAL PROPERTIES: ADDITION REACTIONS ............................................................... 6

    11E SECTION(S) 11.7 ADDITION POLYMERS ................................................................................................................. 8 11F SECTION(S) 11.8 ALKYNES ....................................................................................................................................... 13 11G SECTION(S) 11.9/10 AROMATIC HYDROCARBONS .............................................................................................. 17 11H SECTION(S) 18.2 AMINO ACIDS HAVING SIMPLE AROMATIC SIDE CHAINS ................................................ 22

    11I SECTION(S) 11.11 AROMATIC REACTIONS ........................................................................................................... 23 11J SECTION(S) 11.12 FUSED RING AROMATICS ........................................................................................................ 25 11K SECTION(S) 11.13 HETEROCYCLICS (NOT COVERED IN DETAIL) ................................................................... 26

?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.2 11A Section(s) 11.1/2/4 Introduction and Nomenclature of Alkenes

    ? Ethene = (Ethylene), CH=CH 22

    ? IUPAC Rules

    ? Start numbering from the end that gives the double bond the

    lowest number.

    ? Indicate position of double bond(s) by numbers.

    ? Use the ene ending

    ? Indicated number of double bonds by prefixes (ene, diene, triene,

    tetraene, etc.)

    ? Examples

?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.3

    ? Geometric Isomers

    ? No free rotation (?-bonds)

    ? Experimental observations

    ? cis isomers vs. trans isomers

    ? Examples

    ?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.4 11B Section(s) 11.3 ?-Bonds

    2? Bonding: sp hybridization for 3 ?-bonds to the three atoms

    bonded to each carbon

    ? p orbital for ?-bond z

    ? Typical C=C bond distance (i.e., 1.34

    ?)??????????????????????????

    ????????????????????

    ? slightly shorter C-H distance than alkanes

?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 506 Dr. Hunter’s Class Chapter 11.5

    11C Section(s) 11.5 Physical Properties

    ? Almost identical to Alkanes of same MW

    ? Van der Waals forces

    ? Slightly higher Mp and Bp

    ? Smell (turpentine like)

    ? Density

    ? Solubility

    ?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.6 11D Section(s) 11.6 Chemical Properties: Addition Reactions

    ? Addition reaction (generic)

    ? ?-bonds weaker than ?-bonds

    ? Hydrogenation: Addition of H or D (Pt catalyst) 22

    ? Addition of Cl or Br (X) 222

?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.7

    ? Addition of HX ((HF) HCl, HBr (HI))

    ? Halide Influences

    ? Markovnikov Addition

    ? Addition of Water (Hydration)

    +? H Catalyst

    ? Markovnikov

?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.8 11E Section(s) 11.7 Addition Polymers

    ? Definition of Addition Polymers

    ? No loss of mass

    ? Rapid chain growth

    ? ?-bond opening

    ? “Generic” Synthesis Reaction

    ? typical monomers are CH=CH-R 2

    ? Role of Catalysts

    ? Speed reaction but aren’t themselves consumed

    ? Highly reactive species

    ?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.9

    ? Reversibility of Reactions

    ? Polymerization under low temperatures/high pressures

    ? i.e., monomer (liquids or gasses) -> polymer (solids)

    ? Depolymerizations (unraveling) at high temperatures

    ? i.e., polymer -> monomer

    ? Molecular Weights and Molecular Weight Distributions

    ? High average Molecular Weights

    ? Distributions rather than discrete weights

    ? Linear Chains vs. Branched Chains

    ?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

    Chemistry 506 Dr. Hunter’s Class Chapter 11.10

    ? Examples

    ? Polyethylene, PE, Synthesis

    ? CH=CH, R = H 22

    ? Poly(vinyl chloride), PVC, Synthesis

    ? CH=CH-Cl, R = Cl 2

?2000, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

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