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Chemistry 2100

Chemistry 2100. Fall 2011. Bloom’s Taxonomy. Richard C. Overbaugh, Lynn Schultz Old Dominion University. Student Objectives for this course. Analyze and explain chemical differences among the various classes of organic compounds Evaluate carbohydrate structure and reactivity

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Chemistry 2100

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  1. Chemistry 2100 Fall 2011

  2. Bloom’s Taxonomy Richard C. Overbaugh, Lynn SchultzOld Dominion University

  3. Student Objectives for this course • Analyze and explain chemical differences among the various classes of organic compounds • Evaluate carbohydrate structure and reactivity • Compare and contrast the four main classes of key biomolecules • Explain the processes of protein folding and enzymatic catalysis • Use knowledge of replication, transcription, and translation to predict the outcome of genetic diseases • Relate biochemical concepts to digestion, metabolism, and nutrition

  4. Organic & Biological Chemistry

  5. General Chemistry element covalent bonds lone pairs H 1 0 C 4 0 N 3 1 O 2 2 X 1 3 ~109.5°

  6. Valence Shell Electron Pair Repulsion Theory regions of predicted predicted electron density geometry bond angles 4 tetrahedral 109.5° 3 trigonal planar 120° 2 linear 180° 120° ~109.5° 180° 120°

  7. Meet the Elements http://www.youtube.com/watch?v=Uy0m7jnyv6U

  8. English Language Shorthand Cursive Type Print

  9. The language of Chemistry 3D Structural Formula Molecular Formula C2H6O Structural Formula Skeletal, line-angle Formula Condensed Structural Formula Molecular Representation CH3CH2OH or

  10. Alkanes • Simplest hydrocarbons • Composed of only single bonds • Often referred to as aliphatic hydrocarbons • From Greek aleiphar (fat or oil) • Also called Paraffins • From Latin parum affinis (barely reactive) • General formula: CnH2n+2

  11. Methane & Ethane

  12. Propane & Butane

  13. Butane & Constitutional Isomers C4H10 n-butane isobutane

  14. How many constitutional isomers? constitutional (structural) isomers C20H42 366,319 C30H62> 4 billion C40H82> 65 trillion C20H42 366,319 C30H62 > 4 billion C40H82> 65 trillion C5H123 C6H145 C10H2275

  15. Naming Conventions: IUPAC Nomenclature • International Union of Pure and Applied Chemistry • Gives a set of unambiguous names • Despite this, common names are still used

  16. Naming Alkanes #C Prefix + -ane C1 "meth" Gr., methy (wine)* C2 "eth" Gr., aithein (blaze) C3"prop" Gr., protos pion (first fat)* C4"but" L., butyrum (butter) C5"pent" Gr., pente (five) C6"hex" Gr., hex (six) C7"hept" Gr., hepta (seven) C8"oct" L., octo (eight) C9"non" L., nona (nine) C10"dec" L., deca (ten)

  17. Alkyl groups

  18. Naming Algorithm Parent Substituents— —Suffix IUPAC Rules (a) parent C-chain (b) substituents (c) numbers (d) alphabetical listing

  19. Dreadful Details! • 1. The name for an alkane with an unbranched chain of carbon atoms consists of a prefix showing the number of carbon atoms and the ending -ane. • 2. For branched-chain alkanes, the longest chain of carbon atoms is the parent chain and its name is the root name. • 3. Name and number each substituent on the parent chain and use a hyphen to connect the number to the name. • 4. If there is one substituent, number the parent chain from the end that gives the substituent the lower number.

  20. Dreadful details (part 2)! • 5. If the same substituent occurs more than once: • Number the parent chain from the end that gives the lower number to the substituent encountered first. • Indicate the number of times the substituent occurs by a prefix di-, tri-, tetra-, penta-, hexa-, and so forth. • Use a comma to separate position numbers. • 6. If there are two or more different substituents • List them in alphabetical order. • Number the chain from the end that gives the lower number to the substituent encountered first. • If there are different substituents at equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number. • 7. Do not include the prefixes di-, tri-, tetra-, and so forth or the hyphenated prefixes sec- and tert- in alphabetizing; • Alphabetize the names of substituents first, and then insert these prefixes.

  21. Alkane Origins

  22. Physical Properties of Alkanes

  23. Isomers and Physical Properties pentane bp 36°C; mp -130°C d 0.626 neopentane bp 9°C; mp -16°C d 0.606 isopentane bp 28°C; mp -160°C d 0.620

  24. Alkane Origins

  25. C6-C12 mixture Gasoline, Combustion, & Octane Ratings CH4 + 2O2 CO2 + 2H2O + 212 kcal/mol CH3CH2CH3 + 5 O2 3 CO2 + 4H2O + 530 kcal/mol but… 2 CH3CH2CH3 + 7 O2 2 CO2 + 2 CO + 2 C + 8H2O + < 530 kcal/mol Octane Rating – Controlled Explosions Ethanol Octane rating 105 2,2,4-trimethylpentane (iso-octane) Octane rating 100 Heptane Octane rating 0 Octane Octane Rating -20

  26. Halogenation dichlorodiphenyltrichloroethane DDT polytetrafluoroethylene (PTFE) Teflon dichlorodifluoromethane Freon Perfluorodecalin

  27. 60° 90° 108° 120° 128° 135° Cycloalkanes CnH2n 60° 88° 105° 109° 109° 109°

  28. Cholesterol Muskone Interesting Cycloalkane Derivatives Testosterone Estradiol

  29. Cyclohexane

  30. Cyclohexane – the Chair 6 1 5 4 2 "chair" 3

  31. CH3 CH3 H H H H H H (1) (1) H H 4 4 1 1 H H 2 2 (3) (3) (3) (3) 3 3 2 2 3 3 6 6 (3') (3') (3') (3') 5 5 6 6 5 5 (1) (1) CH3 CH3 1 1 4 4 95% 5% 1,3-diaxial interactions H H Cyclohexane Substituents

  32. H H Cl H Cl H Cl H H Cl H H Cl Cl Cl Cl Haworth perspective Haworth perspective cis-1,2-dichlorocyclopentane trans-1,2-dichlorocyclopentane Geometric Isomers, a.k.a.cis-trans isomers

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