Learning objectives
FIRST AND SECOND MODULES
At the end of the course, the student is expected to acquire knowledge and competence on fundamental organic chemistry. In particular, the student
achieves the following learning goals:
1. knowledge of the main 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 fundamental physical-chemistry principles (chemical equilibria, structural theory, thermodynamics and
kinetics of organic reactions, acids and bases, nucleophiles and electrophiles);
4. knowledge, understanding and prediction 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 prediction 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)
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 class. 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 fundamentals in previous classes. To access the final examination, it is necessary to pass both the “General and Inorganic Chemistry” examination and the Organic Chemistry Basics” written examination.
Course unit content
FIRST MODULE:
After a brief introduction on aims and methods of the course, the following topics are recalled and/or introduced: electronic structure of atoms (with emphasis on C, H, O, N, and main elements in organic molecules), Lewis structure, chemical bonds classification, polarity of molecules and its relationship with molecular structure, atomic orbital hybridation and molecular geometry, theory and application of the resonance theory, identification of functional groups in organic molecules and their classification based on carbon oxidation state, principles of chemical thermodynamics and kinetics, reaction diagrams, use of curly arrows in chemical reactions, acids and bases, nucleophiles and electrophiles. Structure, drawing modalities and nomenclature of alkanes, cycloalkanes, alkenes, and alkynes. Constitutional isomerism, conformational isomerism, physical properties
and reaction types of alkanes and cycloalkanes. Physical properties, geometric isomerism, and reactivity of alkenes; physical properties and
brief introduction on alkyne reactivity. Stereoisomerism (enantiomers, diastereoisomers, meso compounds), properties of stereoisomers, thier drawing and nomenclature; relevance of chirality in the domains of natural products and drugs. Each class of the introduced organic compounds is placed in connection with natural compounds and drugs. A series of exercises are proposed during the class, 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 class.
SECOND MODULE:
Recall of key topics in the "Organic Chemistry Basics” class. The following topics are then treated.
Topic 5. Classification of solvents. Structure and nomenclature of halogenoalkanes, physico-chemical properties, monomolecular and bimolecular nucleophilic substitution reactions at saturated carbon atoms, monomolecular and bimolecular beta-elimination reactions: mechanisms, predction of resulst based on experimental conditions, competition. Connection with biology, drugs, environment.
Topic 6. Structure, nomenclaure, physico-chemical properties of aliphatic alcohols, ethers, epoxides, thiols, thioethers, amines. Reactivity of alcohols as acids, bases, in SN/E reactions, oxidations. Bried introduction on the reactivity of ethers and thiols. Reactions of epoxide opening. Basic (and acid) properties of amines, amines as nucleophiles. Connection with the natural world and drugs.
Topic 7. Structure of benzene, aromaticity, nomenclature of benzene derivatives, their physico-chemical properties. Reaction of electrophilic aromatic substitution: mechanism and applications. Introduction to phenols and their biological relevance. Aromatic amines: structure, synthesis, and biological properties. Main aromatic heterocycles: structure, resonance, relevance in the world of drugs.
Topic 8. Aldehydes and ketones: structure, nomenclature, physico-chemical properties. Reactivity: nucleophilic addition, addition-elimination with ammonia derivatives, redox reactions. Keto-enol tautomerism. Brief introduction to the structure of aldose and ketose monosaccharides, and di- and polysaccharides.
Topic 9. Carboxylic acids: structure, nomenclature, physico-chemical properties, behaviour as acids. Reactions of acylic nucleophilic substitution: Fischer esterification. brief introduction to reduction reactions and decarboxylation. Connection with the natural world, brief introduction to fatty acids. Main acylic derivatives: structure, nomenclature, SNAc reactions with alcohols and amines, their interconversion, brief introduction to reduction reactions with hydrides and Grignard reagents. Brief introductions to the structure of peptides.
Topic 10. Enolate anoin: structure and formation. Aldol reaction, Claisen condensation, Michael addition. Connection with the natural world and drugs.
Full programme
FIRST MODULE:
Topic 0. Genesis and development of the science of organic chemistry. Description of the electronic structure of atoms with particular emphasis
on C, H, N, O, halogens and elements mainly present in organic molecules. Lewis model of chemical bond description, classification of chemical bonds, electronegativity, polarity of molecules and estimation of polar/apolar features of molecules based on their structure. Hybrid atomic orbitals with emphasis on carbon atom, and subsequent prediction of molecular geometry. Classification of the main classes of organic compounds based on the functional groups and the oxidation number of the carbon atom within them. Resonance theory and its application in organic molecules; radical carbon atom, carbocation, carbanion.
Topic 1. Alkanes and cycloalkanes: structure, nomenclature, physical properties, occurrence, drawing modalities (Kekulé structures, condensed, pseudocyclic, zig-zag, Fischer, Newman projections).Configurational and conformational isomers. Conformational analysis of linear alkanes and cycloalkanes, in particular mono- and disubstituted cyclohexanes. Reaction types of alkanes, and connection with biomolecules and drugs.
Topic 2. 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. Catalysis: general concepts. Acids and bases: definition, acid base equilibria, pKa, equilibria position and its prediction based on the structure of the involved species, chemical species in aqueous solutions depending on pH values. Nucleophiles and electrophiles: definition, classification, and factors influencing their behaviour and reactivity.
Topic 3. Alkenes and alkynes: structure, occurrence, nomenclature. Geometric isomerism of alkenes, physical properties, and reactions of alkenes and alkynes: electrophilic addition, redox. Carbocation transpositions. Terminal alkyne acidity and reactions of alkyne anions. Connection with biomolecules and drugs.
Topic 4. Stereoisomers, chirality of organic molecules, enantiomers, diastereoisomers, compounds possessing two or more stereocenters, R and S descriptors, meso compounds. Properties of stereoisomers, brief introduction to the separation of racemates. Significance of chirality in biology and drugs.
SECOND MODULE:
Recall of key topics in the "Organic Chemistry Basics” class. The following topics are then treated.
Topic 5. Classification of solvents. Structure and nomenclature of alkyl halides, physico-chemical properties, monomolecular and bimolecular nucleophilic substitution reactions at saturated carbon atoms, monomolecular and bimolecular beta-elimination reactions: mechanisms, predction of resulst based on experimental conditions, competition. Connection with biology, drugs, environment.
Topic 6. Structure, nomenclaure, physico-chemical properties of aliphatic alcohols, ethers, epoxides, thiols, thioethers, amines. Reactivity of
alcohols as acids, bases, in SN/E reactions, oxidations. Brief introduction on the reactivity of ethers and thiols. Reactions of epoxide opening. Basic
(and acid) properties of amines, amines as nucleophiles. Connection with the natural world and drugs.
Topic 7. Structure of benzene, aromaticity, nomenclature of benzene derivatives, their physico-chemical properties. Reaction of electrophilic
aromatic substitution: mechanism and applications. Introduction to phenols and their biological relevance. Aromatic amines: structure, synthesis, and biological properties. Main aromatic heterocycles: structure, resonance, relevance in the world of drugs.
Topic 8. Aldehydes and ketones: structure, nomenclature, physico chemical properties. Reactivity: nucleophilic addition, addition-elimination with ammonia derivatives, redox reactions. Keto-enol tautomerism. Brief introduction to the structure of aldose and ketose monosaccharides, and
di- and polysaccharides.
Topic 9. Carboxylic acids: structure, nomenclature, physico-chemical properties, behaviour as acids. Reactions of acylic nucleophilic substitution: Fischer esterification. brief introduction to reduction reactions and decarboxylation. Connection with the natural world, brief introduction to fatty acids. Main acylic derivatives: structure, nomenclature, SNAc reactions with alcohols and amines, their interconversion, brief introduction to reduction reactions with hydrides and Grignard reagents. Brief introductions to the structure of peptides.
Topic 10. Enolate anoin: structure and formation. Aldol reaction, Claisen condensation, Michael addition. Connection with the natural world and
drugs.
Bibliography
FIRST AND SECOND MODULES
Choose ONE of the following textbooks (MANDATORY) (the same for both modules):
1. W.H. Brown, T. Poon, “Introduzione alla Chimica Organica”, VII Edizione, EdiSES Università, Napoli, 2023
2. J. Gorzynski Smith, "Fondamenti di Chimica Organica", Quarta Edizione, McGraw-Hill Education, 2023
3. P.Y. Bruice, "Elementi di Chimica Organica", III Edizione, EdiSES Università, Napoli, 2024
Further readings for consultation (at the library of the Science Centre in the Campus):
-W.H. Brown, B. L. Iverson, E. V. Anslyn, C.S. Foote, “Chimica Organica”, VII Edizione, EdiSES, Napoli, 2023
-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. Clayden, N. Greeves, S. Warren, , “Chimica Organica”, Piccin, 2023
-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 loaded on Elly includes:
-slides of each lesson;
-exercises for each subject matter;
-some copies of the text of written examinations of the past academic years
Teaching methods
FIRST and SECOND MODULE
The present course is realized with frontal lessons (both theory and exercises) IN PRESENCE. In particular, the teacher takes lessons in the classroom with the help of PC (Powerpoint slides); the lesson slides are uploaded in Elly.
The teacher also performs exercises (in classroom with the collaboration of students) 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 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, some 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.
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 about 5 (COP) or about 6 (for CO) open-answer questions corresponding to a score detailed in the text. The result is marked in thirtieth, with a minimum pass of 18. The laude (30/30 cum laude) is assigned as a maximum quotation when all questions are correctly answered and when specialized language is used. Each written test contributes for the 45% of the final quotation of the whole examination, while the fianl oral exam contributes for 10%.
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 about 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.
Both written exams as well as and oral exam are carried out IN PRESENCE.
During both written and oral examinations , no books, notes, nor web-related material are permitted ; 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, according to CAI guidelines.
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 final oral examination deals with a brief discussion of the subjects of both modules.
Other information
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