Organic Chemistry – Part I

Upon successful completion of this course, students will be able to:

• draw and name the identified organic functional groups;
• state the IUPAC name (or the common name, if one exists) from the structure of an organic compound containing a functional group identified under Course Content;
• draw any organic compound containing an identified functional group using a bond-line structure, given either its IUPAC or common name;
• identify bonding characteristics of organic molecules, including molecular shape, bond angle, hybridization, molecular orbital count and symmetry type;
• draw structures of all possible isomers and describe each isomer from the molecular formula of an organic compound;
• draw all relevant resonance structures and a resonance hybrid for an organic compound and describe the significance of each resonance structure to the hybrid;
• list the intermolecular forces that apply to a molecule, and predict the physical properties that result from those forces;
• predict the relative acidity and the approximate value of the acid ionization constant (Ka/pKa) of a compound given its molecular structure;
• identify Lewis acids and Lewis bases;
• rank compounds, or sites on a single compound, in order of relative acidity;
• draw any alkane conformation with a Newman projection;
• draw mono-/multi-substituted cyclohexanes in all relevant conformations, indicating axial/equatorial bonds and 1,3-diaxial interactions;
• describe ring strain in cycloalkanes from cyclopropane to cyclohexane;
• describe the factors that affect signal intensity, wavenumber, and signal shape in an infrared (IR) spectrum;
• describe the factors that affect the absorption maximum location in an ultraviolet-visible absorption (UV-Vis) spectrum;
• determine the functional groups present given the IR spectrum of an unknown compound;
• identify the presence of a conjugated electron system;
• identify the location of the absorption maximum from the UV-Vis spectrum of an unknown compound;
• propose plausible bond-line structures for an unknown compound from its molecular formula and IR spectrum;
• identify chiral objects and molecules;
• identify chiral carbons and describe them using the R/S naming system;
• draw molecules with one or more chiral carbons and communicate the correct stereochemistry using any of the following: Fischer projection, Newman projection, or wedge/dash bonds on a bond-line diagram;
• identify a meso compound and draw its stereoisomers;
• describe how to conduct an optical activity experiment using a polarimeter;
• interpret the results of a polarimetry experiment in terms of observed rotation, specific rotation, optical purity, enantiomeric excess, and percent composition;
• state the isomeric relationship between two compounds, the structures of which may be given in any identified projection/conformation/bond-line diagram;
• provide examples of reactions that are one or more of: stereoselective, stereospecific, regioselective;
• describe whether a reaction is under thermodynamic or kinetic control and how this affects the observed outcome;
• sketch a potential energy plot for a reaction including reactants, intermediates, transition states, and products, given the mechanism;
• describe relative reaction rates and the relative stability of chemical species using a potential energy plot;
• rank the relative stabilities of a given a list of carbocations, including resonance-stabilized carbocations;
• identify strong nucleophiles, weak nucleophiles, electrophiles, strong bases, and weak bases and describe their interactions by drawing reaction mechanisms with curved arrows;
• derive and use the rate law equation to describe concentration effects on the rate of any identified reaction;
• rank the relative stabilities of a given list of alkenes;
• predict the major product of any identified organic reaction, given an appropriate chemical substrate and reagent(s);
• state the required reagents to carry out any identified organic reaction given appropriate substrate(s) and product(s);
• draw a complete identified reaction including substrate(s) and reagent(s), given a desired product;
• describe the effect of changing the substrate and/or reagents on the thermodynamic and kinetic properties of any identified reaction;
• draw a complete mechanism to rationalize the products formed for any identified reaction, including curved arrows, by-products, and intermediates, when given a full or partial reaction;
• sketch a reasonable transition state for any mechanistic step in any identified reaction;
• utilize retrosynthesis, as necessary, to design a multi-step synthesis of a target compound using identified reactions, given a desired target molecule and allowed starting materials;
• write a multi-step chemical synthesis using forward reaction arrows, retrosynthesis arrows, or both, as appropriate.