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C341, Page 1 Learning Outcomes and Activities for Chemistry 341 – Organic Chemistry I. Learning Outcome Associated Activities 1 C341.A Understand structures of organic compounds, their classes, and nomenclature 2 3 4 C341.B C341.C Understand structures, isomerism, physical and chemical properties, and practical importance of alkanes and cycloalkanes Understand chirality and stereoisomerism of organic compounds, nomenclature of chiral compounds, their physical and biological properties Understand structures of organic molecules and different ways of their graphic representation Understand hybridization of atomic orbitals and its influence on chemical and physical properties of organic compounds Know and be able to recognize all major functional groups and classes of organic compounds and different ways of their graphic representation Understand and be able to apply major principles of both common and IUPAC nomenclatures of organic compounds 1 Understand structures of alkanes and cycloalkanes and their constitutional isomerism 2 Understand basic principles affecting physical properties of alkanes and cycloalkanes 3 Understand conformations of alkanes and cycloalkanes and different ways of their graphic representation 4 Understand cis,trans isomerism of cycloalkanes and different ways of their graphic representation 5 Understand basic principles affecting chemical behavior of alkanes and cycloalkanes, and oxidation as their primary reaction 6 Know major sources of alkanes and cycloalkanes and their practical importance 1 Understand chirality and stereoisomerism of organic compounds 2 3 Understand and be able to apply principals of naming chiral compounds, including R,S system of stereocenters Understand specific chemical and physical properties of chiral compounds, including compounds with one and two stereocenters 4 Understand optical activity of chiral compounds and methods of its detection and measuring 5 Understand principles and methods of separation of enantiomers and diastereomers 6 Understand significance of chirality in biological world and its practical importance for biological activity of organic compounds Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams C341, Page 2 C341.D C341.E C341.F Understand acidity and basicity of organic compounds and their connection to chemical reactivity Understand structures, isomerism, nomenclature and practical importance of alkenes Understand major chemical reactions of alkenes, including electrophilic addition, oxidation, and reduction 1 Understand structures and functions of BrønstedLowry and Lewis acids and bases 2 Understand principles influencing acidity and basicity of organic compounds, including electronegativity and hybridization of atoms, and charge delocalization 3 Understand acidity and basicity as a basis of chemical reactivity of organic compounds 1 Understand structures of alkenes, their cis,trans isomerism, and nomenclature 2 3 1 Understand the presence of double bond as a major factor that determines chemical reactivity of alkenes 2 Understand electrophilic addition as a major chemical reaction of unsaturated organic compounds 3 4 C341.G Understand transformation of alkanes into highly reactive haloalkanes via radical halogenation Understand and be able to apply principles of designating configuration in alkenes, including cis,trans and E,Z systems Understand and be able to recognize structures of terpenes as a major class of naturally occurring alkenes, know their practical importance Know and understand major examples of electrophilic addition in alkenes, including addition of hydrogen halides, water, and halogens, hydroboration-oxidation, and oxymercuration-reduction. Know and understand major oxidation and reduction reactions of alkenes, and major reagents used in these reactions, including catalytic hydrogenation, oxidation to glycols, and ozonation 1 Understand structures of haloalkanes, haloalkenes, and haloarenes, and their nomenclature 2 Understand factors determining specific physical and chemical properties of haloalkanes 3 Understand the key role of haloalkanes in organic chemistry as reactive derivatives of alkanes 4 Understand radical halogenation as a major method of preparation of haloalkanes from alkanes Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams C341, Page 3 1 2 C341.H Understand nucleophilic aliphatic substitution and β-elimination as a major reaction types in organic chemistry 3 Understand SN1 and SN2 as two major mechanisms of nucleophilic aliphatic substitution 4 Understand β-elimination as a competitor of nucleophilic substitution 5 Understand E1 and E2 as two major mechanisms of βelimination 6 Understand phase transfer catalysis as an important tool facilitating nucleophilic aliphatic substitution 1 2 C341.I Understand structure, nomenclature, properties, reactions, and practical significance of alcohols Understand the role of nucleophilic aliphatic substitution as a major reaction type in organic chemistry Understand major factors affecting nucleophilic substitution, including the role of nucleophile, leaving and neighboring groups, and solvents 3 Understand structure and nomenclature of alcohols and thiols, including primary, secondary, and tertiary alcohols, diols, and poliols Understand the presence of hydroxyl as a major factor determining specific physical and chemical properties of alcohols, including their high boiling points, their acidity and basicity Understand nucleophilic aliphatic substitution and βelimination as major reactions of alcohols, as well as different methods of transforming hydroxyl into a good leaving group, including acid catalysis, conversion to haloalkanes, and tosylation 4 Understand pinacol rearrangement as a major industrial chemical reaction 5 Know and understand different methods and outcomes of oxidation of alcohols, and reagents used there for 6 Understand practical significance and role of alcohols in human history, chemical industry, and environment protection 7 Understand factors determining specific properties of thiols compared to alcohols Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams Daily quizzes, exams C341, Page 4 C341.J Acquire significant practical experience in major methods of isolation and purification of organic compounds, and carrying out chemical reactions. 1 Become proficient in basic methods of separation and isolation of organic compounds, including liquid-liquid extraction, gravity and vacuum filtration, and distillation/evaporation 2 Become proficient in basic methods of characterization of organic compounds, including melting point determination and thin layer chromatography (TLC) 3 Be able to successfully apply TLC for monitoring progress of chemical reactions, separation and purification of reaction products 4 Be able to successfully use open column chromatography to isolate and purify products of chemical reactions 5 Through participation in a real research project acquire significant practical experience in carrying out chemical reactions. The reactions in question may include but will not be limited to aldol condensation and reductive amination 6 Become familiar with modern methods of parallel organic synthesis including application of microwave synthesizers Observation of instructor, and lab notebook Observation of instructor, and lab notebook Observation of instructor, and lab notebook Observation of instructor, and lab notebook Observation of instructor, and lab notebook Observation of instructor, and lab notebook