ORGANIC CHEMISTRY BASICS
Learning outcomes of the course unit
At the end of the course, the student is expected to acquire knowledge and competence on basic organic chemistry.
In particular, the student achieves the following targets:
1. knowledge of the basic functional groups and application of this knowledge for the classification of simple organic molecules;
2. knowledge, understanding and application of the structural representation of simple organic molecules and their visualization in the three-dimensional space also with the help of molecular models;
3. knowledge and understanding of the basic physical-chemistry principles (chemical equilibria, structural theory, thermodynamics and kinetics of organic reactions, acids and bases, nucleophiles and electrophiles);
4. knowledge, understanding and prevision of the relationship between the structure of simple organic molecules (containing the functional groups detailed in the contents section) and their physical properties, in particular their solubility in aqueous or non-aqueous solvents;
5. knowledge, understanding and prevision of the relationship between the structure of simple organic molecules (containing the functional groups detailed in the contents section) and their reactivity (chemical behavior), and application of this ability by solving suitable exercises;
6. knowledge and understanding the methods of synthesis (preparation) and interconversion of simple organic molecules (containing the functional groups detailed in the contents section) and application of these methods for the solution of suitable exercises dealing with the synthesis and transformation of unknown organic molecules;
7. knowledge of the international rules for the nomenclature of simple organic molecules (containing the functional groups detailed in the contents section) and their application in the nomenclature of unknown molecules, also by solving suitable exercises;
8. ability to convey the contents of the course to a specialized audience using appropriate scientific language (both written and oral) (communication skills);
9. understanding the role of organic chemistry basics in the study of drugs and living organisms; ability to link the contents of the course to those of neighboring chemical disciplines (making judgements; learning skills).
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 mandatory to pass the “General and Inorganic Chemistry” examination.
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 a 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, reaction diagrams, 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, alkenes, alkynes. In addition, the general structure and nomenclature of alkyl halides, alcohols, polyols, thiols, ethers, epoxides is given.
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 the science of organic chemistry. Functional groups of the main organic compounds. The carbon atom as a key element in organic chemistry: its electronic configuration, hybrid orbitals, oxidation number within a molecule, valence, electronegativity. Classification of the main classes of organic compounds based on the functional groups and the oxidation number of the carbon atom within them. Radical carbon atom, carbocation, carbanion.
Configurational and conformational isomers. Conformational analysis of linear alkanes and cycloalkanes, in particular mono- and polysubstituted cyclohexanes. Graphical representation of organic molecules (zig-zag modality, pseudocyclic, Fisher projection, Newman projection along carbon-carbon bond axis). Constitutional isomers and stereoisomers. Chirality of organic molecules, enantiomers, diastereoisomers, compounds possessing two or more stereocenters, R and S descriptors, meso compounds, geometric isomerism. Separation of racemates. Significance of chirality in biology and drugs.
Recalling the concepts of chemical equilibrium, equilibrium constants and relationship with the variation of free energy in a given reaction. Reaction kinetics, activation energy, energy profile of a reaction. Thermodynamic vs kinetic control of an organic reaction. Catalysis: general concepts.
Reaction mechanisms, use of curly arrows for their representation. Resonance structures. Representation of radical or ionic reaction mechanisms. Nucleophiles and electrophiles: definition, classification, factors influencing their behavior.
Acid and basic organic compounds. Definition according to Bronsted-Lowry and Lewis. Acid-base equilibria, pKa, equilibria position, dependence of the position of the equilibria upon pH. Factors influencing their behavior.
Classification of main solvents in organic chemistry. Relationship between the molecular structure of a simple organic compound and its polarity and solubility in aqueous/non-aqueous, protic/aprotic, polar/apolar solvents.
Monomolecular and bimolecular nucleophilic substitution reactions at saturated carbon atoms. Monomolecular and bimolecular elimination reactions. Regioselectivity, stereoselectivity, stereospecificity aspects.
Radical halogenation of alkanes; regioselectivity aspects (briefly).
Brief introduction to organometallic compounds; Grignard reagents.
Electrophilic addition reaction to the carbon-carbon double and triple bonds: mechanisms, regioselectivity, stereoselectivity.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of: alkanes, cycloalkanes, alkenes, alkynes. Structure and basic nomenclature of alkyl halides, alcohols, vicinal diols, thiols, aliphatic ethers, epoxides.
Choose ONE of the following textbooks (mandatory) (the same for both modules):
-W.H. Brown, B. L. Iverson, E. V. Anslyn, C.S. Foote, “Chimica Organica”, VI Edizione, EdiSES, Napoli, 2019
-P.Y. Bruice, “Chimica Organica”, Terza Edizione, EdiSES, Napoli, 2017.
-Autori vari, “Chimica Organica” (a cura di B. Botta), Seconda Edizione, Edi.Ermes, Milano, 2016.
-J. Gorzynski Smith, Fondamenti di Chimica Organica, Terza Edizione, McGraw Hill Education, Milano, 2018.
-J. McMurry, “Chimica Organica”, IX Edizione, Piccin, Padova, 2017.
Choose ONE of the following exercize books (mandatory) (the same for both modules):
-M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, Quinta Edizione, Loghia Ed., Napoli, 2020.
-B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote, Iverson – Chimica Organica”, 4° Ed., EdiSES, Napoli, 2016.
-T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
-F. Nicotra, L. Cipolla “Eserciziario di Chimica Organica”, Edises, 2013.
Further readings for consultation (at the library of the Department of Food and Drug):
-J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001
-R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana, Piccin Editore, Padova, 1997
--L. Kürti, B. Czakó, “Strategic Applications of Named Reactions in Organic Synthesis”, Elsevier Academic Press, 2005.
Further material for exercises and examples of the final written examination are loaded on Elly portal:
-exercises (with separate solutions) for each subject matter;
-many copies of the text of written examinations (with separate solutions) of the past academic years.
According to the regulation of the Italian Government and the University of Parma about the COVID-19 pandemics, the present course is realized with frontal lessons (both theory and exercises) via mixed in-presence and at-distance modality. In particular, the teacher takes lessons in the classroom with the help of PC (Powerpoint slides) and board (either graphic table connected to the PC or blackboard); simultaneous connection of the PC to the Teams platform in streaming modality ensures connection with students not present in the classroom. Each lesson is registered and loaded in the Elly portal of the course, together with the slides. The teacher also performs exercises (in classroom with the collaboration of students and simultaneous streaming connection via Teams) in order for the student to: 1) apply the theory to solve practical problems dealing with the contents of the course; 2) verify learning before passing to the subsequent subject; 3) get a method for the execution of exercises.
The student is expected to read and study the contents of the lessons by him/herself by using notes/slides and textbook, and applying this knowledge in the execution of exercises, including 1) the exercises made in classroom, 2) exercises in the textbook and study guides, and 3) exercises assigned during lessons and loaded weekly on the Elly platform. Solutions of exercises are subsequently given by the teacher, for self-evaluation of the students. In addition, many copies of the text of written examinations of the past academic years are loaded and updated in the Elly platform (with solutions), to provide further tools in the preparation of the examination.
The teacher is available for further explanations about theory and exercises in the following moments: 1) at the end or during the break of the lesson, 2) in office or by distance via Teams after e-mail appointment, 3) via chat on Elly platform.
Assessment methods and criteria
To verify the level of knowledge and learning of the student, a written examination is mandatory (1 hour) consisting of 7 or 8 open-answer questions having different weight and corresponding to a score detailed in the text. The result is marked in thirtieth, with a minimum pass of 18; it contributes for the 45% of the final quotation of the whole examination.
To access the final oral examination and subsequent recording, it is also necessary to pass the written examination of the second module (Organic Chemistry). It is possible to carry out the written examination of both modules (Organic Chemistry Basics and Organic Chemistry) in the same date since they are dispensed at different times.
To access the written examination, the student must register on-line (via Essetre) in the dates according to the official examination schedule of the Department of Food and Drug. In addition, the teacher will propose a written examination “in itinere” (November), whose positive result exonerates the students to take the examination later. The successful written test has a validity of 6 months, and the student has to take the remaining tests (written examination of Organic Chemistry and oral test) within this period.
In case the COVID-related sanitary emergence continues, the written examination will proceed as follows: 1) written examination in the classroom (whenever possible); 2) remote written examination on the Teams platform (see the guidelines at the address: http://selma.unipr.it/). The teacher will give the students detailed instructions on the modality to access the examination by remote location (link, ID loading, honour declaration loading).
Whichever the modality of the examination (in presence or remote), no books, notes, nor web-related material are permitted during the examination; possible compensatory material will be allowed to students with DSA or BES, which will be agreed upon with the teacher at least one week before the examination.
The written exam is judged positive (superior or equal to 18/30) when the student demonstrates knowledge and learning of the nomenclature of basic organic molecules, acid-base reactions, writing the structure of simple organic molecules including different conformations and configurations.
The laude (30/30 cum laude) is assigned as a maximum quotation when all questions are correctly answered and when specialized language is used.
The result of the written examination is given within one week from the date of the same exam and anyway before the date of the oral examination of the same session via Essetre portal. The student is expected to view his/her work (either successful or failed), which is consigned the day of the oral session either in presence or by distance via Teams. If the student cannot be present that day, he/she has to inform the teacher by e-mail; the teacher will show the work to the student on another date, to be fixed with the student.