Learning objectives
At the end of the course, the student is expected to acquire and strengthen learning and knowledge of basic organic chemistry.
In particular, the student is expected to have gained the following skills:
1. Knowledge and understanding of the main functional groups and applying them to the classification of simple organic molecules;
2. Knowledge, understanding and applying the structural representation of simple organic molecules and their visualization in the three-dimensional space;
3. Knowledge and understanding of 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 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 and their reactivity;
6. Knowledge and understanding of the methods for the functional group interconversion within simple organic molecules and applying these methods for the synthesis and manipulation of unknown organic molecules, also solving simple exercises;
7. Knowledge the international rules for the nomenclature of simple organic molecules and applying them to unknown molecules, also solving simple exercises;
8. Communication skills of the course contents to specialized and non-specialized audience;
9. Understanding the importance of organic chemistry in the study of drugs and living organisms.
Prerequisites
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 Organic Chemistry I test, it is mandatory to pass the “General and Inorganic Chemistry” exam.
Course unit content
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, as well as their main reactivity. Attention will be paid to basic principles of organic chemistry including the nature of chemical bond and the polarity of the molecules, orbital hybridization and molecular geometry, 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, synthetic methods and the rules of nomenclature for the main classes of organic compounds according to their functional group (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.
Full programme
COURSE OUTLINE
General aspects. 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. Oxidation 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. Nucleophilic substitution at the carbonyl group (acyl nucleophilic substitution). Enols and enolates. Aromaticity: basic concepts.
Structure, nomenclature, natural occurrence, physical properties, reactivity and synthesis of the following organic compound families: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, diols, ethers, thiols, epoxides, aldehydes, ketones, carboxylic acids, acyl halides, anhydrides, esters, lactones, amides, lactams, imides, nitriles, amines, alpha,beta-unsaturated carbonyl compounds.
Bibliography
RECOMMENDED TEXTBOOKS (choose one of the following):
1. W.H. Brown, B.L. Iverson, E.V. Anslyn, C.S. Foote, “Chimica Organica”, VI Ed., EdiSES, Napoli, 2019.
2. J. McMurry, “Chimica Organica”, IX Edizione, Piccin, Padova, 2017.
3. P. Yurkanis Bruice, "Chimica Organica", III Edizione, EdiSES, Napoli, 2017.
4. Autori vari, “Chimica Organica”, II edizione (a cura di B. Botta), Edi.Ermes, Milano, 2016.
WORKBOOKS (choose one of the following):
1. M.V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, Quarta Edizione, Loghia Ed., Napoli, 2017.
2. B.L. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Chimica Organica di Brown, Iverson, Anslyn, Foote", IV Ed., EdiSES, Napoli, 2016.
3. F. Nicotra, L. Cipolla, "Eserciziario di Chimica Organica", Edises, Napoli, 2013.
4. T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
FURTHER READINGS
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.
As additional study tools it will be provided slides presented during lessons and links to access a series of educational videos published by the JoVE Science Education web platform and recommended as innovative learning support.
Copies of the past examination tests to be use for practicing will be also uploaded in the Elly platform.
Teaching methods
According to the regulation of the Italian Government and the University of Parma about the pandemics, the present course is carried out through frontal oral lessons (both theory and exercises) according to an "in-presence" modality (total 64 hours corresponding to 8 CFU). In particular, the teacher takes lessons in the classroom with the help Powerpoint slides, board (graphic table connected to the PC or traditional whiteboard) and educational videos. In case of emergency, lessons may be registered and loaded in the Elly portal of the course (with access allowed to attending students), together with the slides. Exercises dealing with synthesis and manipulation of simple organic molecules will be proposed and solved by either the teacher or the students. The exercise sessions are open to free discussion between students and teacher and this is considered an essential part of the course with the aim to:
-check applying knowledge and understanding of proposed contents;
-check the ability to master the acquired theoretical concepts and to apply knowledge in analyzing and solving problems of organic chemistry;
-check learning skills and communication skills.
The student is expected to read and study the contents of the lessons by him/herself by using notes and textbook, and applying this knowledge in solving the exercises, including both the exercises proposed in classroom, and exercises in the textbook and study guide.
To stimulate regular class attendance, the video recording of each lesson will be accessible through the Elly platform for one week.
The teacher is available (on e-mail appointment) for further explanations about theory and exercises in office or by distance via Teams.
The additional material (slides) is weekly loaded on Elly platform; this material does not substitute the textbook and the exercise study guide, which are mandatory.
Many copies of past written tests are loaded and updated in the Elly platform, to provide further tools in preparation of the examination.
Assessment methods and criteria
Knowledge and learning are verified by a written test followed by an oral exam.
The written test consists of 4-5 questions (open-answer) dealing with the synthesis and the reactivity of simple organic compounds.
The result is marked in thirtieth, with a minimum pass of 18 and it contributes for the 50% of the final quotation.
To access the written test, the student must register on-line (via ESSE3 portal) in the dates according to the official agenda of the Food and Drug Department.
During the written test, the consultation of books, notes, or web-related material is forbidden; 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 (> or equal to 18/30) when the student demonstrates the following skills:
-knowledge and understanding of the functional groups (as detailed in the contents) within simple organic molecules and their nomenclature;
-applying knowledge and understanding in the identification of carbon stereocenters, asymmetry and chirality;
-applying knowledge and understanding in relating the structural properties and the reactivity of organic compounds;
-applying knowledge and understanding in predicting the outcome of a chemical transformation;
-selecting information from the theory to analyze and solve a practical organic chemistry problem;
-completing synthesis sequences and interconversion of functional groups of simple organic compounds.
To access the final oral colloquium and subsequent recording, it is necessary to pass the written test. The result of the written test is given within one week and in any case before the oral examination via ESSE3 portal.
The oral colloquium is intended to test and confirm the student knowledge and understanding of the contents of the course, to check communication skills and the correct use of specialized language.
The result of the final exam is the arithmetic mean of both written and oral tests and is marked in thirtieth; a minimum of 18/30 is required as a threshold.
"In-progress test": during the course, one "in-progress test" (not mandatory) is given, focused on the first part of the program. Passing the in-progress test allows the student to take a shortened written test.
The mark (in thirtieth) for the partial test contributes one third to the mark for the written test.
Other information
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