Learning objectives
FIRST AND SECOND MODULES
At the end of the course, the student is expected to acquire knowledge and competence on basic organic chemistry.
In particular, the student will be on 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 of, understanding and applying 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 of, and understanding 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 carrying out suitable exercises (knowledge and understanding; applying knowledge and understanding).
6. Knowledge of, 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 carrying out 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 applying them for the nomenclature of unknown molecules, also by carrying out 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 necessary to pass the “General and Inorganic Chemistry” exam.
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 necessary to pass both the “General and
Inorganic Chemistry” exam and the Organic Chemistry Basics” exam.
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, 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.
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: 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”, V Edizione, EdiSES, Napoli, 2014
-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.
- P.Y. Bruice, “Chimica Organica”, Terza Edizione, EdiSES, Napoli, 2017.
Choose one of the following exercise 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”, seconda Edizione, Loghia Ed., Napoli, 2011.
-B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote, Iverson – Chimica Organica”, 4° Ed., EdiSES, Napoli, 2014.
-T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
-S. Cacchi, F. Nicotra, “Esercizi di Chimica Organica”, Casa Editrice Ambrosiana, 1998
Further readings available at the Food and Drug Department (as a suggestion for specific subjects, not mandatory) (the same for both modules):
-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.
Many copies of the text of written examinations (in some cases with solutions) of the past academic years are loaded and updated in the Elly platform, to provide further tools in preparation of the examination.
Teaching methods
FIRST MODULE
The course is carried out through frontal oral lessons at the blackboard (total 40 hours corresponding to 5 CFU) including exercises. The exercises are carried out by either the teacher or the students and are considered an essential part of the course in order to:
-applying the theory to solve practical problems dealing with the contents of the course;
-verifying the status of knowledge before passing to the subsequent subject;
-acquire 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 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.
The teacher is available for further explanations about theory and exercises at the end of the lesson, during the break or in office on e-mail appointment.
The teacher may sometimes use additional teaching material (slides) loaded on the Elly platform; this material is considered optional and does not replace the textbook and the exercise study guide, which are mandatory.
Many copies of the text of written examinations of the past academic years are loaded and updated in the Elly platform (some of them with solutions), to provide further tools in preparation of the examination.
SECOND MODULE
The course is carried out through frontal oral lessons at the blackboard (total 56 hours corresponding to 7 CFU) including exercises. The exercises are carried out by either the teacher or the students and are considered an essential part of the course to:
-applying the theory to solve exercises dealing with the contents of the course;
-verifying the status of knowledge before passing to the subsequent subject;
-acquire a method for the execution of exercises in both the synthetic direction (synthesis of a target molecule), and retrosynthetic direction (disconnection of a target molecule).
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 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.
The teacher is available for further explanations about theory and exercises at the end of the lesson, during the break or in office on e-mail appointment.
The teacher may sometimes use additional teaching material (slides) loaded on Elly platform; this material is considered optional and does not substitute the textbook and the exercise study guide, which are mandatory.
Many copies of the text of written examinations of the past academic years are loaded and updated in the Elly platform (some of them with solutions), to provide further tools in preparation of the examination.
Assessment methods and criteria
FIRST MODULE
To verify the level of knowledge and learning of the student, a written examination is mandatory (1 hour and 45 minutes maximum length) consisting of 7/8 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. It is possible to carry out the written examination of both modules in the same date since they are 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 Food and Drug Department.
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. While carrying out the examination, as a rule, no books, notes nor whatever information system must be available. The student is expected to view his/her work which is consigned the day of the oral session. 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.
SECOND MODULE
To verify the level of knowledge and learning of the student, a written examination is mandatory (2 hour and 15 minutes maximum length) consisting of 4-5 (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 of the integrated course, it is necessary to pass the written examination of both modules. To access the written examination, the student must register on-line (via Essetre) in the dates according to the official examination agenda of the Food and Drug Department.
The written exam 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. While carrying out the examination, as a rule, no books, notes, nor whatever information system must be available.
The result of the written examination is usually given within one week from the date of the same exam and anyway before the oral examination of that session via Essetre portal. The student is expected to view his/her work which is consigned on the day of the oral session. Once written examinations of both modules are passed, the student must attend the final oral examination (10-20 minutes, 10% weight) in the date of the same session of the last written examination. The on-line registration via Essetre to access the oral examination is suggested but not mandatory.
Other information
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