Organic Chemistry
A.Y. 2026/2027
Learning objectives
The teaching aims to provide the student with the knowledge necessary for understanding the structure of organic molecules and their most common reactions, through the description of the main classes of organic compounds, the study of their chemical and physical characteristics, their reactivity and methods of obtaining them with frequent connections between organic compounds and the world around us. The learning of the concepts and notions acquired, will be helped by synchronous classroom and self-assessment exercises on digital platforms. Explanatory videos will also be made available to facilitate learning of more complex mechanisms.
Expected learning outcomes
At the end of the course, the student will have acquired knowledge about the structure, chemical and physical properties of the main classes of organic compounds, will be able to critically analyse organic molecules on the basis of their structure, recognizing their acidity/basicity, nucleophilicity/electrophilicity, and stereochemistry, understand and predict the reactivity of organic molecules on the basis of the functional groups in the molecular structure. (Dublin Descriptor 1: Knowledge and Ability to Understand)
He/she will know how to apply the concepts of hybridization, covalent, polar, sigma and π bonding, isomerization and resonance to organic compounds; he/she will be able to recognize the functional groups present in the structures and assign IUPAC names. In addition, the student will gain knowledge of the mechanisms of chemical transformations and be able to predict the products of a reaction from analysis of the reactants, catalysts and reaction conditions used. This ability will be developed by conducting classroom exercises through discussion between students and the teacher. In addition, periodic verification of understanding of the skills acquired will be possible through the performance of exercises chosen by the teacher, available on an online platform. (Dublin Descriptor 2: Ability to apply knowledge and understanding).
The student will acquire the ability to propose simple synthetic strategies for the preparation of chemical compounds and to predict the physical characteristics and reactivity of organic molecules. (Dublin Descriptor 3: Critical and judgmental skills).
The student will be expected to acquire the ability to use vocabulary and terminology related to Organic Chemistry to transfer knowledge. (Dublin Descriptor 4: Ability to communicate what has been learned.)
By the end of the course, the student will have acquired the foundation for learning the preparatory topics for teachings of the subsequent years. (Dublin Descriptor 5: Ability to pursue independent study
He/she will know how to apply the concepts of hybridization, covalent, polar, sigma and π bonding, isomerization and resonance to organic compounds; he/she will be able to recognize the functional groups present in the structures and assign IUPAC names. In addition, the student will gain knowledge of the mechanisms of chemical transformations and be able to predict the products of a reaction from analysis of the reactants, catalysts and reaction conditions used. This ability will be developed by conducting classroom exercises through discussion between students and the teacher. In addition, periodic verification of understanding of the skills acquired will be possible through the performance of exercises chosen by the teacher, available on an online platform. (Dublin Descriptor 2: Ability to apply knowledge and understanding).
The student will acquire the ability to propose simple synthetic strategies for the preparation of chemical compounds and to predict the physical characteristics and reactivity of organic molecules. (Dublin Descriptor 3: Critical and judgmental skills).
The student will be expected to acquire the ability to use vocabulary and terminology related to Organic Chemistry to transfer knowledge. (Dublin Descriptor 4: Ability to communicate what has been learned.)
By the end of the course, the student will have acquired the foundation for learning the preparatory topics for teachings of the subsequent years. (Dublin Descriptor 5: Ability to pursue independent study
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Single session
Responsible
Lesson period
Second semester
Course syllabus
INTRODUCTION: Review of the concepts of hybridization, bond types and polarity, intermolecular interactions, resonance structures, acidity and basicity, molecular structure, and acidity scales, with application to organic compounds.
HYDROCARBONS: Alkanes, alkenes, and alkynes. Nomenclature. Physical properties, reactivity, and methods of preparation. Conformational analysis of linear and cyclic alkanes. Newman projections. Substituted cycloalkanes: steric effects and cis-trans and E/Z isomerism.
Types of organic reactions: addition, elimination, substitution, and rearrangement. Reaction mechanisms: radical and polar reactions. Electrophilic addition to carbon-carbon double and triple bonds: Markovnikov's rule. Addition of water, hydrogen halides, halogens, and hypohalous acids. Hydrogenation, oxidation, and hydroxylation.
STEREOCHEMISTRY: Geometry of carbon-containing compounds. Molecular representations. Constitutional isomers. Chirality and stereogenicity. Fischer projections. Enantiomers, diastereomers, and meso compounds. Optical activity and polarimetry. Resolution of racemic mixtures. Cahn-Ingold-Prelog nomenclature.
ALKYL HALIDES: Nomenclature. Physical and chemical properties. Halogenated compounds and chlorofluorocarbons (CFCs). Nucleophilic substitution reactions (SN1 and SN2): mechanisms and stereochemical consequences. Carbocations: stability and rearrangements. Elimination reactions (E1 and E2). Factors influencing reaction mechanisms. Competition between substitution and elimination.
ALCOHOLS, ETHERS, AND EPOXIDES: Nomenclature. Physical properties. Hydrogen bonding. Acidity and basicity. Reactivity and methods of preparation.
THIOLS AND THIOETHERS: Nomenclature. Physical properties and acidity.
ALDEHYDES AND KETONES: Nomenclature. Structure and physical properties. Nucleophilic addition to the carbonyl group: addition of oxygen, nitrogen, and carbon nucleophiles. Oxidation and reduction reactions. Methods of preparation. Keto-enol tautomerism and racemization.
CARBOXYLIC ACIDS: Physical properties and acidity. Salt formation. Methods of preparation: oxidation, carboxylation, and hydrolysis of derivatives. Reduction reactions. Substitution reactions involving the hydroxyl hydrogen and the hydroxyl group.
CARBOXYLIC ACID DERIVATIVES: Acyl chlorides, acid anhydrides, esters, amides, and nitriles. Nucleophilic acyl substitution, hydrolysis, and reduction reactions. Methods of preparation.
REACTIONS AT THE α-CARBON OF CARBONYL COMPOUNDS: Acidity of α-hydrogen atoms. Tautomerism. Enols and enolates. Halogenation, alkylation, aldol condensation, and inter- and intramolecular Claisen condensation.
AMINES: Physical properties. Basicity. Synthesis by direct and indirect alkylation (Gabriel synthesis). Reductive methods: reduction of amides, nitriles, and azides; reduction of imines, enamines, and nitro compounds. Reactions with nitrous acid.
AROMATIC HYDROCARBONS: Structure of benzene. Aromaticity: Hückel's criteria. Nomenclature. Reactions at the benzylic position: oxidation and radical halogenation. Electrophilic aromatic substitution (EAS): halogenation, nitration, sulfonation, and Friedel-Crafts alkylation/acylation. Activating, deactivating, and directing effects of substituents.
PHENOLS AND ANILINES: Acidity and basicity. Methods of preparation and reactivity.
HETEROCYCLIC COMPOUNDS: Definition and overview. Five-membered aromatic heterocycles: pyrrole, furan, and thiophene; electrophilic aromatic substitution reactions. Pyrrole: acid-base properties. Six-membered aromatic heterocycles: pyridine; basicity and reactivity in electrophilic and nucleophilic aromatic substitution (EAS and SNAr).
CARBOHYDRATES: Classification. Stereochemistry: epimers. Hemiacetal structures: anomers and Haworth projections. Mutarotation. Reactions of monosaccharides: glycoside formation, oxidation, and reduction. Disaccharides and polysaccharides.
AMINO ACIDS: Classification. Stereochemistry. Acid-base properties: isoelectric point. Introduction to the reactivity of α-amino acids: esterification and acylation. Peptides and the peptide bond.
HYDROCARBONS: Alkanes, alkenes, and alkynes. Nomenclature. Physical properties, reactivity, and methods of preparation. Conformational analysis of linear and cyclic alkanes. Newman projections. Substituted cycloalkanes: steric effects and cis-trans and E/Z isomerism.
Types of organic reactions: addition, elimination, substitution, and rearrangement. Reaction mechanisms: radical and polar reactions. Electrophilic addition to carbon-carbon double and triple bonds: Markovnikov's rule. Addition of water, hydrogen halides, halogens, and hypohalous acids. Hydrogenation, oxidation, and hydroxylation.
STEREOCHEMISTRY: Geometry of carbon-containing compounds. Molecular representations. Constitutional isomers. Chirality and stereogenicity. Fischer projections. Enantiomers, diastereomers, and meso compounds. Optical activity and polarimetry. Resolution of racemic mixtures. Cahn-Ingold-Prelog nomenclature.
ALKYL HALIDES: Nomenclature. Physical and chemical properties. Halogenated compounds and chlorofluorocarbons (CFCs). Nucleophilic substitution reactions (SN1 and SN2): mechanisms and stereochemical consequences. Carbocations: stability and rearrangements. Elimination reactions (E1 and E2). Factors influencing reaction mechanisms. Competition between substitution and elimination.
ALCOHOLS, ETHERS, AND EPOXIDES: Nomenclature. Physical properties. Hydrogen bonding. Acidity and basicity. Reactivity and methods of preparation.
THIOLS AND THIOETHERS: Nomenclature. Physical properties and acidity.
ALDEHYDES AND KETONES: Nomenclature. Structure and physical properties. Nucleophilic addition to the carbonyl group: addition of oxygen, nitrogen, and carbon nucleophiles. Oxidation and reduction reactions. Methods of preparation. Keto-enol tautomerism and racemization.
CARBOXYLIC ACIDS: Physical properties and acidity. Salt formation. Methods of preparation: oxidation, carboxylation, and hydrolysis of derivatives. Reduction reactions. Substitution reactions involving the hydroxyl hydrogen and the hydroxyl group.
CARBOXYLIC ACID DERIVATIVES: Acyl chlorides, acid anhydrides, esters, amides, and nitriles. Nucleophilic acyl substitution, hydrolysis, and reduction reactions. Methods of preparation.
REACTIONS AT THE α-CARBON OF CARBONYL COMPOUNDS: Acidity of α-hydrogen atoms. Tautomerism. Enols and enolates. Halogenation, alkylation, aldol condensation, and inter- and intramolecular Claisen condensation.
AMINES: Physical properties. Basicity. Synthesis by direct and indirect alkylation (Gabriel synthesis). Reductive methods: reduction of amides, nitriles, and azides; reduction of imines, enamines, and nitro compounds. Reactions with nitrous acid.
AROMATIC HYDROCARBONS: Structure of benzene. Aromaticity: Hückel's criteria. Nomenclature. Reactions at the benzylic position: oxidation and radical halogenation. Electrophilic aromatic substitution (EAS): halogenation, nitration, sulfonation, and Friedel-Crafts alkylation/acylation. Activating, deactivating, and directing effects of substituents.
PHENOLS AND ANILINES: Acidity and basicity. Methods of preparation and reactivity.
HETEROCYCLIC COMPOUNDS: Definition and overview. Five-membered aromatic heterocycles: pyrrole, furan, and thiophene; electrophilic aromatic substitution reactions. Pyrrole: acid-base properties. Six-membered aromatic heterocycles: pyridine; basicity and reactivity in electrophilic and nucleophilic aromatic substitution (EAS and SNAr).
CARBOHYDRATES: Classification. Stereochemistry: epimers. Hemiacetal structures: anomers and Haworth projections. Mutarotation. Reactions of monosaccharides: glycoside formation, oxidation, and reduction. Disaccharides and polysaccharides.
AMINO ACIDS: Classification. Stereochemistry. Acid-base properties: isoelectric point. Introduction to the reactivity of α-amino acids: esterification and acylation. Peptides and the peptide bond.
Prerequisites for admission
Basic knowledge of General and Inorganic Chemistry is required, with particular reference to atomic structure, chemical bonding, periodic trends of the elements, stoichiometry, chemical equilibrium, acids and bases, and the main properties of solutions. Basic mathematical skills necessary to perform simple chemical calculations are also recommended. These competencies are normally acquired during upper secondary education or through the General Chemistry courses included in the degree programme.
Teaching methods
The course includes face-to-face lectures and online learning activities delivered in synchronous formats. Teaching will employ active and interactive learning methods, with particular emphasis on student engagement through group activities and problem-solving exercises designed to reinforce the topics covered during the lectures.
Teaching Resources
Brown - Foote - Iverson, Chimica Organica, Edises.
Bruice, Chimica Organica, Edises.
D'Auria Taglialatela, Zampella Guida ragionata allo svolgimento di esercizi di Chimica Organica, Loghia.
Supplementary course materials are available on the professor's MyAriel website, including lecture slides, practice exercises, past examination papers, and additional learning resources.
Bruice, Chimica Organica, Edises.
D'Auria Taglialatela, Zampella Guida ragionata allo svolgimento di esercizi di Chimica Organica, Loghia.
Supplementary course materials are available on the professor's MyAriel website, including lecture slides, practice exercises, past examination papers, and additional learning resources.
Assessment methods and Criteria
Learning outcomes will be assessed through a written examination designed to verify the achievement of the course learning objectives. The examination will include questions aimed at assessing students' knowledge of the structure, nomenclature, properties, and reactivity of the main classes of organic compounds, as well as their understanding of the principal reaction mechanisms and their ability to solve simple organic chemistry problems. Assessment will be based on the accuracy and completeness of the answers, together with the ability to apply the acquired knowledge to the proposed questions. The final grade will be expressed on a 30-point scale.
Professor(s)