Organic Chemistry – Part II

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

• describe the physical basis of nuclear magnetic resonance (NMR);
• describe basic NMR experiment design;
• calculate the hydrogen deficiency index from a molecular formula;
• predict the number of peaks and their respective chemical shifts, splitting patterns, and integrations in a ¹H  or ¹³C NMR spectrum from the structural formula of an organic compound;
• determine a plausible structure of an unknown organic compound, given any combination of its: chemical formula, infrared (IR) spectrum, ultraviolet-visible absorption (UV-Vis) spectrum, mass spectrum, ¹H NMR spectrum, ¹³C NMR spectrum;
• state the IUPAC name (or the common name, if one exists) when given 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 its IUPAC or common name, as appropriate;
• recognize identified oxidizing and reducing agents, and identify the transformations they induce;
• predict the relative potential energy of each organic radical, given a group of such radicals;
• draw resonance structures to describe the relative potential energy of an allylic radical;
• predict whether an allylic substitution (diene) reaction will be thermodynamically or kinetically controlled;
• rank the relative speeds of various Diels–Alder reactions, given a list of potential dienes and dienophiles;
• explain the potential energy of benzene using molecular orbital theory;
• predict whether a given organic compound is aromatic, non-aromatic, or anti-aromatic;
• draw the sigma complex from an electrophilic aromatic substitution reaction mechanism and all relevant resonance structures;
• predict where on its structure a substituted-benzene substrate will add an additional electrophile in an electrophilic aromatic substitution reaction;
• describe the rate, relative to unsubstituted benzene, at which a substituted-benzene substrate will undergo an electrophilic aromatic substitution reaction;
• draw keto and enol tautomers and describe how to manipulate their equilibrium;
• select an appropriate base to irreversibly form an enolate from a carbonyl compound;
• predict if a reaction will occur by addition to the carbonyl group, or at the carbon alpha to the carbonyl group, given a suitable substrate;
• describe the similarities and differences in the reactivities of carboxylic acids and their derivatives;
• describe the effects of carboxylic acid structure on acidity;
• describe how to manipulate a condensation mechanism to produce starting materials or products;
• 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 reaction including substrate(s) and/or 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 mechanism and its outcome;
• draw a complete mechanism to rationalize the products formed for any identified organic reaction, including curved arrows, by-products, and intermediates, when given a full or partial reaction;
• draw and distinguish acid- and base-catalyzed versions of an identified reaction mechanism, where appropriate;
• sketch a reasonable transition state for any mechanistic step in any identified organic reaction;
• design a multi-step synthesis of a target compound using identified organic reactions when given a target molecule and allowed starting materials.