1 2008 Lecture 2 3 4_Functional_groups Alkanes Cycloalkanes

1 2008 Lecture 2 3 4_Functional_groups Alkanes Cycloalkanes...

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Chem 2203/2207 There are no formally scheduled tutorials! Assignments and Lecture Notes are posted On http://http-server.carleton.ca/~pbuist/
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Introduction to Functional Groups, Alkanes and ycloalkanes Cycloalkanes Chapter 3,4
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Functional Groups • A functional group is a collection of atoms that confers unique physical and chemical properties on an organic molecule.
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Non-functionalized carbon framework 1. Acyclic (not in a ring) CH 3 CH 2 CH 2 CH 2 CH 3 2. Cyclic (ring) 3. Arenes/Aromatic ring (cyclic system with alternating double bonds in a 6- membered ring)
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Functional group Nomenclature tidbits example No functional group on carbon backbone C-C double bond triple bond (Alkane) Alkene - ane - ene C-C triple bond Also called: Hydroxyl Also called: Mercaptan OH SH Alkyne Alcohol Thiol - yne - ol - thiol
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Functional group Nomenclature tidbits S O Ether Sulfide -ether -Sulfide (thioether) Other halides can also be functional groups (i.e. Br = bromo, I = Iodo NH 2 Cl Amine (amino) Alkyl chloride (chloro) -amine -halide
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Functional Group Nomenclature tidbits H O O Aldehyde Ketone -al -one Carboxylic acid family Carboxylic acid family OH O O O O NH 2 Carboxylic acid Ester Amide -oic acid -oate -amide
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Functional Group Nomenclature tidbits Carboxylic acid family Nitrile, cyanide Carboxylic acid family Cl O C N O O Acid Chloride Cyano Acid -oyl chloride -nitrile -phenol -aniline O OH NH 2 Anhydride Phenol Aromatic Amine -oic anhydride
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Functional groups on Penicillin S N H Amide Sulfide N O O C OH O Carboxylic Acid β -Lactam ring Cyclic amide
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The Penicillin Story
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The Discovery of Penicillin • …took place in a St. Mary’s Hospital laboratory on the second floor of the corner Tower . . facing Praed St. The laboratory window would have been open allowing fungal spores to enter….
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Alkanes • Fully saturated hydrocarbons – Maximum number of Hydrogens per Carbon CH 4 (methane) CH H thane) C 2 H 6 = CH 3 -CH 3 (ethane) C 3 H 8 = CH 3 -CH 2 -CH 3 (propane) . . . C n H 2n+2 = general formula for an alkane
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Alkanes • No functional groups • Also called “aliphatic” hydrocarbons • Tetrahedral geometry
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Geometry and Electronic Structure • Why tetrahedral? To maximize distance between bonds and minimize repulsion between hydrogens arbon atom has 4 • Carbon atom has 4 valence electrons. – Promote a 2s electron to a 2p orbital and then mathematically reconfigure to give 4 equivalent sp 3 hybrid orbitals
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sp 3 hybridization • Four sp 3 orbitals are arranged in a tetrahedral array, one valence electron in each
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4 sp 3 orbitals on C overlap with 1 s orbitals on 4 H atoms to form four identical C-H sigma ( σ ) bonds • Each C–H bond has a strength of 438 kJ/mol nd length of 110 pm (1.1 Angstroms, 0.11 nm). and length of 110 pm (1.1 Angstroms, 0.11 nm). • Each H–C–H bond angle is ~109.5°(tetrahedral)
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1 2008 Lecture 2 3 4_Functional_groups Alkanes Cycloalkanes...

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