Learning objectives
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 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
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” examination.
Course unit content
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 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 reactiivity 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.
Full programme
Topic 0. Genesis and development of the science of organic chemistry. Description of the electronic structure of atoms with particual emphasis of 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.
Bibliography
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 EdizioneItaliana, 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
The course is carried out in presence through frontal oral lessons (slides) and exercises. The exercises are carried out by either the teacher or the students and are considered an essential part of the course to be able to:
-apply the theory to solve practical problems dealing with the contents of the course;
-verify the status of knowledge before passing to the subsequent subject;
-acquire a method for the execution of execises.
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 both the exercises made in classroom, and exercises in the textbook.
The teacher is available for further explanations about theory and exercises at the end of the lesson, during the break, or in office upon agreement with the teacher via e-mail.
The teacher provides loading of lesson slides and exercises on each topic on the Elly platform; this material is considered of help to the students but DOES NOT REPLACE the textbook (which is mandatory).
Some copies of the text of written examinations of the past academic years are loaded and updated in the Elly platform, to provide further tools
in preparation of the examination.
Assessment methods and criteria
To verify the level of knowledge and learning of the student, a written examination is mandatory (1 hour), consisting of about 5 open-answer questions corresponding to a partial score detailed in the text. The overall score is marked in thirtieth, with a minimum pass of 18; the laude (30/30 cum laude) is assigned as a maximum score when all questions are correctly answered and when specialized language is used. The score of this partial written examination contributes for the 45% of the score of the whole final 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 given at different times.
To access the written examination, the student must register on-line (via Essetre) according to the official examination schedule of the Department of Food and Drug.
The successful written test has a validity of about 6 months, and the student must take the remaining tests (written examination of Organic Chemistry and oral test) within this period. The written exam is held in PRESENCE.
In addition to the essetre exam schedule, the teacher will propose a written examination “in itinere” (in November), whose positive result will dispense the students to take the same examination later.
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.
No books, notes, nor web-related materials 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, according to the CAI guidelines.
The student is expected to view his/her work (either successful or failed), which is consigned the day of the oral session.
Other information
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