ORGANIC CHEMISTRY I
Learning outcomes of the course unit
Aim of the course is to acquire knowledge and understanding of 1) the basic principles relating the structure of the main families of organic compounds to their properties and reactivity, 2) the principles underlying organic reactions that allow the rational interpretation of reaction mechanisms.
Another goal of the course is to acquire the skills — that is the ability to apply knowledge and understanding of rules and principles underlying organic reactions — to solve problems of organic chemistry by predicting the outcome of chemical transformations and critically addressing the design of synthetic sequences to prepare simple organic compounds.
Finally, the course aims at the achievement of learning skills and communication skills by employing appropriate language to both specialized and non-specialized audience, in line with the above mentioned objectives.
At the end of the course, the student is expected to be able to master the acquired theoretical concepts and to apply knowledge and understanding to address the execution of problems and exercises about recognizing and analyzing the relationships between structure and reactivity of organic molecules, predicting the outcome of chemical reactions and proposing solutions to synthesize, interconvert and transform organic molecules.
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 first part of the course will be devoted to present the fundamentals of organic chemistry emphasizing the key connections between the molecular structure of organic compounds and their physical and chemical properties and reactivity. Attention will be paid to basic principles of organic chemistry including hybridization and molecular geometry, electronegativity and polarity of the molecules, acidity and basicity, nucleophilicity and electrophilicity, resonance, isomerism and chirality.
The second part of the course will be devoted to the systematic description of reactivity, physical properties and synthetic methods of the main classes of organic compounds (alkanes, cycloalkanes, alkenes, alkynes, halo-alkanes, alcohols and diols, aldehydes, ketones, etc.). In this context, particular emphasis will be given to the description of reaction mechanisms, highlighting similarities and featuring aspects of different reaction pathways.
Origin and development of organic chemistry as a science. Carbon as the focal element in organic chemistry. Functional groups featuring the main organic compound families. Relationships between molecular structure and physical- chemical behavior. Three-dimensional shape of molecules: conformation and configuration of stereogenic centers. Conformational analysis of linear and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality, enantiomers, diastereoisomers, meso compounds, geometrical isomers. Thermodynamic and kinetic control of organic reactions. Reaction kinetics, activation energy, catalysis. Reaction mechanisms. Resonance in organic compounds. Radical and ionic reactions. Oxidations and reduction of organic compounds. Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry. Monomolecular and bimolecular nucleophilic substitution reactions at saturated carbons. Monomolecular and bimolecular elimination reactions. Solubility and solvents used in organic chemistry. Electrophilic additions to alkenes. Regioselective, stereospecific, and stereoselective organic reactions. Nucleophilic addition to carbon-oxygen double bond. Organometallic compounds and Grignard reagents. Nucleophilic substitution at the carbonyl group (Acyl nucleophilic substitution). Role of protecting groups in organic synthesis. Carbon-carbon bond-forming reactions. Enols and enolates: alpha-alkylation and alpha-halogenation.
Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following organic compound families: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, diols, ethers, epoxides, aldehydes, ketones, carboxylic acids, acyl halides, anhydrides, esters, lactones, amides, lactams, imides, nitriles, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds, amines.
Aromaticity. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following organic compound classes: benzene, , alkyl benzenes, phenols, aryl halides and aromatic amines. Structure, nomenclature and reactivity of heterocyclic aromatic compounds.
1. W.H. Brown, B.L. Iverson, E.V. Anslyn, C.S. Foote, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2015.
2. J. McMurry, “Chimica Organica”, VIII Edizione, Piccin, Padova, 2013.
3. Autori vari, “Chimica Organica” (a cura di B. Botta), Edi.Ermes, Milano, 2011.
4. M. Loudon, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2010.
5. P. Yurkanis Bruice, "Chimica Organica", Seconda Edizione, EdiSES, Napoli, 2012.
1. M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, Seconda Edizione, Loghia Ed., Napoli, 2009.
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.
1. J. Clayden, N. Greeves, S. Warren, “Organic Chemistry”, Second Edition, Oxford University Press,. 2012.
2. L. Kürti, B. Csakò, “Strategic Applications of Named Reactions in Organic Synthesis”, 1st Edition, Academic Press, 2005.
According to the above mentioned objectives and contents, the course is carried out through frontal oral lessons. Exercises dealing with the design, synthesis, and transformation of simple organic molecules will be proposed allowing the student to check applying knowledge, understanding and learning skills, in line with the above mentioned objectives.
The exercise sessions are open for free discussion between students and teacher and these are considered an essential part of the course.
Assessment methods and criteria
The final exam consists of a written test followed by an oral colloquium (in case the written test has been passed). The written test deals with solving problems on the synthesis and reactivity of organic compounds. The test aims to verify whether the student has developed skills in relating the structural properties and reactivity of organic compounds, in predicting the behavior of organic compounds under given chemical conditions, in predicting the outcome of a chemical transformation, in selecting and exploiting information from the theory study to solve a practical organic chemistry problem.
The oral colloquium will focus on the contents of the course to check communication skills and the correct use of specialized language.
The result of the exam is marked in thirtieth, a minimum of eighteen thirtieth is required as a threshold.