Learning objectives
FIRST AND SECOND MODULES
At the end of the course, the student is expected to acquire knowledge and competence on organic chemistry.
In particular, the student will achieve the following targets:
1. knowledge of the basic and advanced functional groups and applying this knowledge for the classification of simple polyfunctionalized organic molecules (knowledge and understanding; applying knowledge and understanding);
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 (knowledge and understanding; applying knowledge and understanding);
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) and application of these principles to the study of simple polyfunctionalized organic molecules (knowledge and understanding; applying knowledge and understanding);
4. knowledge, understanding and prevision of the relationship between the structure of simple polyfunctionalized 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 (knowledge and understanding; applying knowledge and understanding);
5. knowledge, understanding and prevision of the relationship between the structure of simple polyfunctionalized organic molecules (containing the functional groups detailed in the contents section) and their reactivity (chemical behavior), also by solving suitable exercises (knowledge and understanding; applying knowledge and understanding);
6. knowledge and understanding the methods of synthesis (preparation) and interconversion of simple polyfuntionalized organic molecules (containing the functional groups detailed in the contents section) and applying these methods for the synthesis and transformation of unknown organic molecules, also by solving suitable exercises (knowledge and understanding; applying knowledge and understanding);
7. knowledge of the international rules for the nomenclature of simple polyfunctionalized organic molecules (containing the functional groups detailed in the contents section) and application of them for the nomenclature of unknown molecules, also by solving suitable exercises (knowledge and understanding; applying knowledge and understanding);
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).
Prerequisites
FIRST MODULE: 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.
SECOND MODULE:
To fully appreciate the content of the course, it is necessary to acquire knowledge of general and inorganic chemistry and organic chemistry basics in previous courses. To access the final examination, it is mandatory to pass both the “General and Inorganic Chemistry” exam and the Organic Chemistry Basics” written test.
Course unit content
FIRST MODULE: 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 physicochemical
properties, recalling some general concepts from the General Chemistry
course including thermodynamics principles, the kinetics and the structural theories.
The key concepts of 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.
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.
SECOND MODULE:
The first part of the course is devoted to recall and advance knowledge acquired in
the (Organic Chemistry Basics” course. The following subjects are then treated:
nucleophilic addition to carbon-oxygen double bond, acyl nucleophilic substitution,
brief description of the role of protecting groups in organic synthesis, brief survey of
qualitative identification of the main functional groups. The systematic study of the
following compound classes is then placed, comprising the structure, nomenclature,
natural occurrence, physical properties, reactivity, and synthesis of the following
compound classes: halogeno-alkanes, alcohols, polyols, ethers, epoxides, thiols, aldehydes, ketones, carboxylic acids, acyl halides, acid
anhydrides, esters, thioesters, lactones, amides, lactams, imides, nitriles, 1,3-
dicarbonyl compounds, alpha,beta-unsaturated compounds, aliphatic and aromatic
amines, nitro- and nitroso-derivatives.
The second part of the course allows students to acquire knowledge on carboncarbon
bond-forming reactions, synthesis of enols and enolates, imines and
enamines, alpha-alkylation and alpha-halogenation of enols and enolates, aldol
additions and condensations and variants thereof, Claisen condensations and
related reactions, Michael and Mannich addition reactions, examples of
transposition reactions.
The third part of the course allows students to acquire knowledge on the aromatic
domain including the concept of aromaticity and the systematic study of aromatic
compounds including the structure, nomenclature, natural occurrence, physical
properties, reactivity, and synthesis of the following compound classes: benzene,
substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines,
simple aromatic heterocycles, azo-compounds.
Full programme
FIRST MODULE: 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.
SECOND MODULE:
The first part of the course is devoted to recall and advance knowledge acquired in
the “Organic Chemistry Basics” course. The following subjects are then treated:
nucleophilic addition to carbon-oxygen double bond, acyl nucleophilic substitution,
brief description of the role of protecting groups in organic synthesis (carbonyl
compounds, phenols, aniline), brief survey of qualitative identification of the main
functional groups. The systematic study of the following compound classes is then
placed, comprising the structure, nomenclature, natural occurrence, physical
properties, reactivity, and synthesis of the following compound classes: aldehydes,
ketones, carboxylic acids, acyl halides, acid anhydrides, esters, thioesters, lactones,
amides, lactams, imides, nitriles, 1,3-dicarbonyl compounds, alpha,betaunsaturated
compounds, amines, nitro- and nitroso-derivatives.
The second part of the course allows students to acquire knowledge on carboncarbon
bond-forming reactions, synthesis of enols and enolates, imines and
enamines, alpha-alkylation and alpha-halogenation of enols and enolates, aldol
additions and condensations and variants thereof, Claisen condensations and
related reactions, Michael and Mannich addition
reactions, examples of transposition reactions.
The third part of the course allows students to acquire knowledge on the aromatic
domain including the concept of aromaticity and the systematic study of aromatic
compounds including the structure, nomenclature, natural occurrence, physical
properties, reactivity, and synthesis of the following compound classes: benzene,
substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines,
simple aromatic heterocycles, azo-compounds.
Bibliography
FIRST AND SECOND MODULES
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.
Teaching methods
FIRST and SECOND MODULE
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 in both retrosynthesis (disconnection of a target molecule) and synthesis (preparation of a target molecule) directions.
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
1° and 2° MODULE
To verify the level of knowledge and learning of the student, a written test for each module is mandatory (1 hour long for Chimica Organica Propedeutica, COP, and 2 hours for Chimica Organica, CO) consisting of 7/8 (COP) or 4/5 (for CO) 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; each test contributes for the 45% of the final quotation of the whole examination.
To access each of the written examinations, the student must register on-line (via Essetre) in the dates according to the official examination schedule of the Food and Drug Department. In addition, students have the occasion to carry out the COP written test “in itinere” (in November) and, if successful, they will be allowed to access to the second test (CO) without repeating the first one. The partial test of COP has a validity of 6 months, period along which the student must carry out the second written test and the final oral examination.
To access the final oral examination and subsequent recording, it is necessary to pass both written tests of the two modules. It is possible to carry out both tests in the same date since they are given at different times. To access the oral examination, the student may register via Essetre, but it is not mandatory.
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 test of COP 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 written exam of CO is judged positive (superior or equal to 18/30) when the student demonstrates knowledge and learning of the following contents: identification and knowledge of the functional groups (as detailed in the contents) within natural or drug-like polyfunctional molecules; identification of carbon stereocenters and chirality; knowledge of the main aromatic and heteroaromatic cyclic compounds with the corresponding resonance structures; execution (even partial) of exercises on synthesis sequences and interconversion of functional groups; execution (even partial) of exercises on the total synthesis of simple organic compounds. 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 each 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.
Other information
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