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CHEM 203 Important Topics for Review – See Chapters 1-3 of Brown-Foote-Iverson Chapter 1 Covalent bonding in organic molecules Covalent bonding as "electron-sharing" between atomic pairs Particularly stable electronic configuration of inert (= noble) gases Principle: atoms in a bonded state tend to acquire an electronic configuration similar to that of a noble gas Bonding in methane: σ-bonds Valence Shell Electron Pair Repulsion (VSEPR) Tetrahedral shape of methane predicted by VSEPR and confirmed by experiment Use of wedges-and-dashed lines to represent the spatial orientation of atoms in a molecule H atoms in the plane of the paper C H H H hash: atom projecting away from the observer wedge: atom projecting toward the observer Association of tetrahedral geometry about a carbon atom with sp3 hybridization Possible occurrence of multiple bonds (double, triple) between atoms in an molecule Bonding in ethene (ethylene), CH2=CH2: a molecule containing a C-C double bond σ-Framework and π-bonds leftover p-type atomic orbitals !-framework H H C C H H sideways overlap of p-type orbitals H C C H H H "-bond Trigonal geometry of the carbon atoms in ethene (ethylene) and related structures as predicted by VSEPR and as confirmed by experiment Association of trigonal geometry about a carbon atom with sp2 hybridization Bonding in ethyne (acetylene), H–C C–H: a molecule containing a C-C triple bond Presence of two independent π-bonds in acetylene leftover p-type atomic orbitals (in the plane of the paper) !-framework H C C H sideways overlap of "dark" "-bond # 1 H C C and "light" p-orbitals H "-bond # 2 leftover p-type atomic orbitals (perpendicular to the paper) Linear geometry of the carbon atoms in acetylene and related structures as predicted by VSEPR and as confirmed by experiment Association of linear geometry about a carbon atom with sp hybridization Functional groups Resonance Chapter 2 Alkanes: structure, isomerism, and conformation (eclipsed, staggered forms) Cycloalkanes (only monocylic molecules; i.e., those containing only 1 ring) Conformations of cyclohexane (chair, boat, twist-boat) Cis-trans isomerism in cycloalkanes Axial and equatorial bonds in a chair cyclohexane Chapter 3 Stereoisomers Enantiomers Optical activity Specific rotation Chirality Centers of chirality Stereogenic atoms / centers R and S convention for designation of configuration of stereogenic centers Diastereomers meso compounds racemic compounds and their resolution into the two enantiomers Fischer projections.