ORGANIC CHEMISTRY BASICS
Learning outcomes of the course unit
Aim of the course is to acquire knowledge and understanding, concepts and learning skills within the following domains:
1) Students should learn and understand the basic language of organic chemistry;
2) students should learn and understand the basic principles which connect the structure of organic compounds with their physico-chemical properties;
3) students should learn and understand the key concepts of the basic organic chemistry course in view of further in-depth study in the subsequent organic chemistry course.
At the end of the course, students having followed all the theory and exercise lessons are expected to be able to applying knowledge and understanding of the above mentioned subject areas through the correct execution of problems and exercises about:
1) recognizing, writing and naming the main organic molecule classes (recognizing the main functional groups);
2) viewing simple organic molecules in three dimensions with an emphasis to their stereochemical properties;
3) recognizing and analyzing the relationship between structure and properties (reactivity) of basic organic molecules including alkanes, cycloalkanes, halogeno-alkanes, alkenes, alkynes, alcohols, polyols, ethers, epoxides, thiols;
4) proposing viable solutions as how to retro-synthesize, synthesize, transform, and interconvert the above mentioned organic compounds.
Further aim of the course involves the acquisition of learning skills and communication skills by employing appropriate language to both specialized and non-specialized audience, in line with the above mentioned objectives.
To fully appreciate the content of the course, it is necessary to acquire knowledge of general and inorganic chemistry in a previous course. To access the final examination, it is necessary to pass the “General and Inorganic Chemistry” exam.
Course contents summary
The introduction of the course is devoted to a general presentation of organic chemistry as a scientific discipline, with a brief overview of its historical background and an highlight of the significance and impact of organic chemistry on contemporary science, culture, and life. Basic principles are then given emphasizing the key connections between the structure of organic compounds and their physico-chemical properties, recalling some general concepts from the General Chemistry course including thermodynamics principles, the kinetics and the structural theories. The key concepts of covalent and ionic bonds, molecular geometry, resonance, acids and bases in organic chemistry, and isomerism are given (conformational and configurational isomers) and an emphasis is placed to stereoisomerism. The second part of the course comprises the systematic study of basic organic compounds including the structure, nomenclature, natural occurrence, physical properties, reactivity, and synthetic methods of alkanes, cycloalkanes, halogeno-alkanes, alkenes, alkynes, alcohols, polyols, ethers, epoxides, thiols.
During the course, a series of exercises are proposed and solved at the blackboard, with the purpose to applying the principles and concepts into a “real-world” context. These exercises are open for free discussion between teacher and students and they are considered an essential part of the course.
Origin and development of organic chemistry as a science. Functional groups of the main organic compounds. The carbon atom as a focal element in organic chemistry. Oxidation number assignment to a given atom within an organic molecule with a special emphasis on the carbon atom. Relationship between the structure of an organic compound and its physical and chemical behaviour. Hybridation (in aprticulr of the carbon atom within organic molecules), molecular geometry, electronegativity, polarity of organic compounds. Resonance in organic compounds. Configurational and conformational isomerism. Conformational analysis of linear and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality, enantiomers, diastereoisomers, meso compounds, geometric isomerism. Thermodynamic and kinetic control of organic reactions. Reaction kinetics, activation energy, catalysis. Reaction mechanisms. Radical and ionic reactions. Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry, acid-base reactions. Oxidative-reductive reactions. Monomolecular and bimolecular nucleophilic substitutions at saturated carbons. Monomolecular and bimolecular beta-elimination reactions. Main solvents and their use in organic chemistry. Organometallic reagents, Grignard reagents: generality and use. Electrophilic addition reactions to alkenes and alkynes. Regioselective, stereospecific, and stereoselective organic reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, polyols, thiols, ethers, epoxides.
Textbooks (one of the following to be chosen):
1. W.H. Brown, C.S. Foote, B. L. Iverson, E. V. Anslyn, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2015.
2. Autori vari, “Chimica Organica” (a cura di B. Botta), Edi.Ermes, Milano, 2011.
3. J. McMurry, “Chimica Organica”, VIII Edizione, Piccin, Padova, 2012.
4. M. Loudon, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2010.
5. J. G. Smith, "Chimica Organica", McGraw-Hill, Milano, 2007.
6. G.H. Schmid, “Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1997.
Study guide and solution manual for exercises (at least one of the following to be chosen):
1. M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, seconda Edizione, Loghia Ed., Napoli, 2011.
2. B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote, Iverson – Chimica Organica”, 3° Ed., EdiSES, Napoli, 2006.
3. T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
4. S. Cacchi, F. Nicotra, “Esercizi di Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1998.
1. J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001.
2. R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana, Piccin Editore, Padova, 1997.
3. R.T. Morrison, R.N. Boyd, “Chimica Organica”, VI Edizione, Casa Editrice Ambrosiana, 1997.
Additional teaching material for students:
Examples of organic chemistry exercises given in the previous examination sessions.
According to the above mentioned objectives and contents, the course is carried out through frontal oral lessons and includes exercises at the blackboard dealing with the design, synthesis, and transformation of simple organic molecules which could be connected with the pharmaceutical and biological domains. These exercises are open for free discussion between teacher and students and they are considered an essential part of the course.
Assessment methods and criteria
The final examination consists of a written exam. The written exam deals with the execution of exercises on the synthesis and reactivity of organic compounds. This test is aimed at verifying whether the student has developed the skill and ability of 1) using the language of organic chemistry, 2) recognizing the basic functional groups, 3) recognizing the relationship between structure and properties of basic organic compounds, 4) predicting the behavior of a given organic chemistry transformation among those comprised in the program, 5) selecting and deploying information from the theory study in order to furnish solutions to a given practical organic chemistry problem.
The result of the written exam is marked in thirtieth. A minimum of eighteen thirtieth is required as a threshold.
Since the “Organic Chemistry Basics” course is complemented by the subsequent “Organic Chemistry” course, the final marking is given by the arithmetic mean of the quotations of each part.