Course Syllabus

CHEM 2320 Organic Chemistry II

Course Description

CHEM 2320 is the second semester of a full-year course in organic chemistry, which is the study of the structures and properties of compounds primarily composed of carbon and hydrogen. Reactivity is studied in the context of mechanism patterns associated with functional groups, with emphasis on synthesis and biochemical applications. This course is required for all chemistry-centered majors, most pre-professional programs, and many life science majors, and is commonly taken in the second year of study.

Justification

Organic chemistry is taught by chemistry departments at USHE institutions. It is a two-semester sequence that is numbered as CHEM 2310 for the first semester and CHEM 2320 for the second semester at USHE institutions. It is required for all chemistry-based majors and many pre-professional programs; some programs require only the first semester. This course will provide a thorough foundation in organic structures, reaction mechanisms, and elementary synthesis methods.

Student Learning Outcomes

1. Students will learn the nomenclature, physical properties, chemical reactivity, preparation, and use in synthesis of common organic functional groups.
2. Students will be able to interpret and draw structures of organic molecules using a variety of representations, such as skeletal structures, Newman projections, Fisher projections, cyclohexane chairs, etc, and transform structures given in one representation into a different representation while maintaining correct regio- and stereochemistry.
3. Students will be able to correctly describe relationships between chemical structures, such as resonance contributors, tautomers, various types of isomers, and reactant-product transformations.
4. Students will be able to write correct curved arrow formalism mechanisms for foundational organic reaction types in isolation and as components of a moderately complex overall molecular transformation.
5. Students will understand the synthetic utility of foundational organic reaction types and be able to construct multi-step synthesis pathways for moderately complex molecules.
6. Students will apply principles of chemical reactivity and structure analysis to predict the major and minor products of organic reactions.
7. Students will be able to integrate spectral and reaction data to determine the structure of an unknown compound.

Course Content

Chemistry 2320 is the second semester of a full-year introductory organic chemistry course. This course provides a fundamental and foundational description of the properties and behavior of carbon-based molecules, which are the primary constituents of all known living systems and many materials upon which modern lifestyles rely. Topics and concepts will be presented such that they build upon one another, with later topics reinforcing and developing concepts introduced with earlier topics. In the first half of the semester, instructors may choose to cover the material in either of the following organizational patterns, corresponding to the pattern being used in the first semester.Topic Set A: mass spectroscopy (MS); ultraviolet-visible light (UV-Vis) spectroscopy; infrared (IR) spectroscopy; nuclear magnetic resonance (NMR) spectroscopy; nucleophilic addition-elimination reactions of carboxylic acids and carboxylic acid derivatives; reactions of aldehydes and ketones with nucleophiles; hydride reduction of carbonyl compounds; use of protecting groups in synthesis; nucleophilic addition to alpha,beta-unsaturated carbonyl compounds; reactions of enolate anions; decarboxylation of beta-keto carboxylic acids; use of carbonyl reactions in synthesis; electrophilic aromatic substitution of benzenes; nucleophilic aromatic substitution of benzenes; synthesis of multi-substituted benzenes; reactions and synthesis of amines; and reactions of five- and six-membered ring aromatic heterocycles. Topic Set B: organolithium and organomagnesium compounds; transmetallation; organocuprates; palladium-catalyzed coupling reactions; radical halogenation of alkanes; radical addition to alkenes; radical substitution at benzylic and allylic positions; use of radical reactions in synthesis; nucleophilic addition-elimination reactions of carboxylic acids and carboxylic acid derivatives; reactions of aldehydes and ketones with nucleophiles; hydride reduction of carbonyl compounds; use of protecting groups in synthesis; nucleophilic addition to alpha,beta-unsaturated carbonyl compounds; reactions of enolate anions; decarboxylation of beta-keto carboxylic acids; use of carbonyl reactions in synthesis; electrophilic aromatic substitution of benzenes; nucleophilic aromatic substitution of benzenes; synthesis of multi-substituted benzenes; reactions and synthesis of amines; and reactions of five- and six-membered ring aromatic heterocycles. In the second half of the semester, instructors may choose at their discretion four to six of the more advanced topics typically contained in the last several chapters of organic chemistry textbooks, comprising: properties and reactions of carbohydrates; properties and reactions of amino acids, peptides, and proteins; catalysis in laboratory and biological settings; structure and biological activity of vitamins; reactions of metabolic pathways and terpene biosynthesis; properties and reactions of nucleic acids; synthesis and structural properties of polymers; and pericyclic reactions.