Organic Chemistry
A.Y. 2026/2027
Learning objectives
The teaching aims to provide the student with the fundamental knowledge required to understand the structure of organic molecules and their main reactions, through the study of the most important classes of organic compounds, their physicochemical properties, reactivity and methods of synthesis with frequent connections to the real-world applications. The learning of the concepts and knowledge is supported by synchronous classroom and self-assessment exercises on digital platforms, and explanatory videos available on the course's Ariel website. The course also includes a laboratory, aimed at developing the skills necessary for the proper conduct of an organic chemistry experiment, including basic safety rules for the handling and disposal of organic substances. Laboratory activities focus on fundamental techniques of purification (recrystallization (recrystallization, distillation, and chromatography), separation (extraction) and the study of the reactivity of selected classes of organic compounds.
Expected learning outcomes
At the end of the course, students will be able to relate the structure, physicochemical properties, and reactivity of the main classes of organic compounds by applying fundamental concepts (chemical bonding, isomerism, resonance, functional groups, and IUPAC nomenclature).
They will also be able to describe the main reaction mechanisms, predict their products, and propose simple synthetic strategies, critically evaluating molecular properties.
Students will be able to use the language of organic chemistry to communicate results and prepare brief reports.
They will have acquired basic skills to safely perform simple laboratory operations, as well as the foundational knowledge required for subsequent courses in Environmental Chemistry, Biochemistry, Food Chemistry, and Chemical Toxicology.
They will also be able to describe the main reaction mechanisms, predict their products, and propose simple synthetic strategies, critically evaluating molecular properties.
Students will be able to use the language of organic chemistry to communicate results and prepare brief reports.
They will have acquired basic skills to safely perform simple laboratory operations, as well as the foundational knowledge required for subsequent courses in Environmental Chemistry, Biochemistry, Food Chemistry, and Chemical Toxicology.
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
Bonding and Structure of Organic Molecules. Electronic structure of the carbon atom. Ionic and covalent bonding, polar covalent bonds, atomic and molecular orbitals, hybrid orbitals. Single and multiple bonds. Resonance theory. Non-bonding intermolecular interactions. Acid-base equilibrium. Molecular structure and acidity. Composition, structure, and formulas of organic molecules. Functional groups and classes of compounds.
ALKANES. Nomenclature; structural isomerism. Conformational isomerism, Newman projections, conformational analysis of ethane and butane. Reactions of alkanes. Combustion: relative stability of alkanes, heats of formation. Radical halogenation. Alkyl radicals.
CYCLOALKANES. Nomenclature; cis-trans isomerism, ring strain. Cyclohexane and substituted cyclohexanes, conformational aspects.
ALKENES. Nomenclature. Structure and E/Z isomerism. Relative stability, heats of hydrogenation. Synthesis via elimination reactions. Reactivity: electrophilic addition of HX, water, and halogens; hydroboration and applications. Oxidation reactions. Reduction to alkanes.
ALKYNES. Nomenclature. Acidity. Synthesis and reactivity: electrophilic additions. Reductions.
Stereochemistry. Chirality and chiral molecules. Enantiomers: representations, Fischer projections, absolute configuration (R/S), optical activity. Molecules with multiple stereocenters: diastereomers and meso compounds. Stereoisomerism in cyclic compounds. Stereochemical course of reactions. Stereoselective reactions. Optical activity and polarimetry. Resolution of racemic mixtures.
HALOALKANES. Nomenclature. Reactivity: nucleophilic substitution and elimination. SN1 and SN2 mechanisms: effects of leaving group, nucleophile, substrate structure, and solvent on reaction rate; stereochemistry. Carbocations: structure and stability. E1 and E2 mechanisms.
ALCOHOLS, ETHERS, AND EPOXIDES. Nomenclature. Physical properties. Hydrogen bonding. Acidity and basicity. Reactivity and preparation methods. Reactions of epoxides with nucleophiles.
Thiols and Thioethers. Nomenclature. Physical properties and acidity. Oxidation. Reactivity as nucleophiles.
ORGANOMETALLIC COMPOUNDS. Preparation and reactivity.
ALDEHYDES AND KETONES. Nomenclature and physicochemical properties. Keto-enol tautomerism. Reactivity: nucleophilic addition; oxidation and reduction. Preparation methods.
CARBOXYLIC ACIDS. Nomenclature, physicochemical properties. Synthesis. Reactivity: nucleophilic acyl substitution.
DERIVATIVES OF CARBOXYLIC ACIDS. Acyl chlorides, anhydrides, esters, amides, and nitriles. Nucleophilic acyl substitution, hydrolysis and reduction reactions. Preparation methods.
Α-CARBONYL REACTIONS. Acidity of α-hydrogens. Enols and enolates. Halogenation, alkylation, aldol and Claisen condensations (inter- and intramolecular).
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 and Hückel's rule. Nomenclature. Benzylic reactions: oxidation and radical halogenation. Electrophilic aromatic substitution: halogenation, nitration, sulfonation, Friedel-Crafts alkylation/acylation. Activating/deactivating and directing effects of substituents.
PHENOLS AND ANILINES. Acidity and basicity. Preparation and reactivity. Reactions of anilines with nitrous acid: diazonium salts and their synthetic applications.
HETEROCYCLIC COMPOUNDS. Definition and overview. Five-membered aromatic heterocycles (pyrrole, furan, thiophene): electrophilic aromatic substitution. Pyrrole: acid-base properties. Six-membered heterocycles (pyridine): basicity and reactivity in electrophilic and nucleophilic substitution.
PHOSPHORUS COMPOUNDS. Phosphines and phosphites: nucleophilic and reducing character. Phosphorous acid, phosphonic acids, phosphonates. Phosphoric acid and phosphate esters. Hydrolysis.
CARBONIC ACID DERIVATIVES. Urea, phosgene, carbamates, diimides: synthesis and relevance.
CARBOHYDRATES. Classification. Stereochemistry: epimers. Hemiacetal structures: anomerism and Haworth projections. Mutarotation. Reactions of monosaccharides: glycosidation, oxidation, reduction. Disaccharides and polysaccharides.
AMINOACIDS. Classification. Stereochemistry. Acid-base properties: isoelectric point. Basic reactivity: esterification and acylation. Peptides and the peptide bond.
POLYMERS. Classification and nomenclature. Addition and condensation polymers.
Laboratory
Basic rules of safety in the laboratory. Purification techniques: distillation, crystallization. Acid/base separation techniques. Separation of organic mixtures with aqueous solutions of varying pH. Chromatographic separation techniques: thin layer chromatography (TLC) and column chromatography.
ALKANES. Nomenclature; structural isomerism. Conformational isomerism, Newman projections, conformational analysis of ethane and butane. Reactions of alkanes. Combustion: relative stability of alkanes, heats of formation. Radical halogenation. Alkyl radicals.
CYCLOALKANES. Nomenclature; cis-trans isomerism, ring strain. Cyclohexane and substituted cyclohexanes, conformational aspects.
ALKENES. Nomenclature. Structure and E/Z isomerism. Relative stability, heats of hydrogenation. Synthesis via elimination reactions. Reactivity: electrophilic addition of HX, water, and halogens; hydroboration and applications. Oxidation reactions. Reduction to alkanes.
ALKYNES. Nomenclature. Acidity. Synthesis and reactivity: electrophilic additions. Reductions.
Stereochemistry. Chirality and chiral molecules. Enantiomers: representations, Fischer projections, absolute configuration (R/S), optical activity. Molecules with multiple stereocenters: diastereomers and meso compounds. Stereoisomerism in cyclic compounds. Stereochemical course of reactions. Stereoselective reactions. Optical activity and polarimetry. Resolution of racemic mixtures.
HALOALKANES. Nomenclature. Reactivity: nucleophilic substitution and elimination. SN1 and SN2 mechanisms: effects of leaving group, nucleophile, substrate structure, and solvent on reaction rate; stereochemistry. Carbocations: structure and stability. E1 and E2 mechanisms.
ALCOHOLS, ETHERS, AND EPOXIDES. Nomenclature. Physical properties. Hydrogen bonding. Acidity and basicity. Reactivity and preparation methods. Reactions of epoxides with nucleophiles.
Thiols and Thioethers. Nomenclature. Physical properties and acidity. Oxidation. Reactivity as nucleophiles.
ORGANOMETALLIC COMPOUNDS. Preparation and reactivity.
ALDEHYDES AND KETONES. Nomenclature and physicochemical properties. Keto-enol tautomerism. Reactivity: nucleophilic addition; oxidation and reduction. Preparation methods.
CARBOXYLIC ACIDS. Nomenclature, physicochemical properties. Synthesis. Reactivity: nucleophilic acyl substitution.
DERIVATIVES OF CARBOXYLIC ACIDS. Acyl chlorides, anhydrides, esters, amides, and nitriles. Nucleophilic acyl substitution, hydrolysis and reduction reactions. Preparation methods.
Α-CARBONYL REACTIONS. Acidity of α-hydrogens. Enols and enolates. Halogenation, alkylation, aldol and Claisen condensations (inter- and intramolecular).
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 and Hückel's rule. Nomenclature. Benzylic reactions: oxidation and radical halogenation. Electrophilic aromatic substitution: halogenation, nitration, sulfonation, Friedel-Crafts alkylation/acylation. Activating/deactivating and directing effects of substituents.
PHENOLS AND ANILINES. Acidity and basicity. Preparation and reactivity. Reactions of anilines with nitrous acid: diazonium salts and their synthetic applications.
HETEROCYCLIC COMPOUNDS. Definition and overview. Five-membered aromatic heterocycles (pyrrole, furan, thiophene): electrophilic aromatic substitution. Pyrrole: acid-base properties. Six-membered heterocycles (pyridine): basicity and reactivity in electrophilic and nucleophilic substitution.
PHOSPHORUS COMPOUNDS. Phosphines and phosphites: nucleophilic and reducing character. Phosphorous acid, phosphonic acids, phosphonates. Phosphoric acid and phosphate esters. Hydrolysis.
CARBONIC ACID DERIVATIVES. Urea, phosgene, carbamates, diimides: synthesis and relevance.
CARBOHYDRATES. Classification. Stereochemistry: epimers. Hemiacetal structures: anomerism and Haworth projections. Mutarotation. Reactions of monosaccharides: glycosidation, oxidation, reduction. Disaccharides and polysaccharides.
AMINOACIDS. Classification. Stereochemistry. Acid-base properties: isoelectric point. Basic reactivity: esterification and acylation. Peptides and the peptide bond.
POLYMERS. Classification and nomenclature. Addition and condensation polymers.
Laboratory
Basic rules of safety in the laboratory. Purification techniques: distillation, crystallization. Acid/base separation techniques. Separation of organic mixtures with aqueous solutions of varying pH. Chromatographic separation techniques: thin layer chromatography (TLC) and column chromatography.
Prerequisites for admission
The student must have a good knowledge of general chemistry fundamentals, with particular attention to atomic structure, nature of the chemical bond, principles of chemical equilibrium, acid and base.
Teaching methods
Teaching will include classroom lectures and online training activities, synchronous and asynchronous (5CFU). The course will make use of active and interactive methods, emphasizing student involvement through group activities as well (1CFU).
Online learning tests (via the Exam Manager app) will be carried out to check the level of learning. The teaching also includes laboratory activities (2 CFU).
Online learning tests (via the Exam Manager app) will be carried out to check the level of learning. The teaching also includes laboratory activities (2 CFU).
Teaching Resources
MyAriel site:
- Lecture slides
- Classroom exercises
- Introductory laboratory lecture slides
- In-depth videos
· W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote - Chimica Organica - VII ed., 2023, Edises, Napoli
· W. H. Brown, T. Poon - Introduzione alla Chimica Organica - VII ed., 2023 - Edises, Napoli
· Paula Yurkanis Bruice - Elementi di Chimica Organica - III ed., 2024 Edises, Napoli
· J. McMurry Fondamenti di Chimica Organica - quarta edizione - Ed. Zanichelli
· M. S. Erickson "Guida alla soluzione dei problemi" da "Introduzione alla Chimica Organica" quinta ed., 2016 - Ed. Edises, Napoli
· Peter C Vollhardt, Neil E Schore - Chimica Organica - IV ed,
· Peter C Vollhardt, Neil E Schore - Esercizi risolti di chimica organica. 2016 - Ed. Zanichelli, Bologna Con
· Slides available on the teacher's Ariel website
For laboratory:
· D.L.Pavia, G.M.Lampman, G.S. Kriz Il laboratorio di Chimica Organica Ed. Sorbona
·M.D'Ischia La Chimica Organica in laboratorio- Ed Piccin - Bologna
- Lecture slides
- Classroom exercises
- Introductory laboratory lecture slides
- In-depth videos
· W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote - Chimica Organica - VII ed., 2023, Edises, Napoli
· W. H. Brown, T. Poon - Introduzione alla Chimica Organica - VII ed., 2023 - Edises, Napoli
· Paula Yurkanis Bruice - Elementi di Chimica Organica - III ed., 2024 Edises, Napoli
· J. McMurry Fondamenti di Chimica Organica - quarta edizione - Ed. Zanichelli
· M. S. Erickson "Guida alla soluzione dei problemi" da "Introduzione alla Chimica Organica" quinta ed., 2016 - Ed. Edises, Napoli
· Peter C Vollhardt, Neil E Schore - Chimica Organica - IV ed,
· Peter C Vollhardt, Neil E Schore - Esercizi risolti di chimica organica. 2016 - Ed. Zanichelli, Bologna Con
· Slides available on the teacher's Ariel website
For laboratory:
· D.L.Pavia, G.M.Lampman, G.S. Kriz Il laboratorio di Chimica Organica Ed. Sorbona
·M.D'Ischia La Chimica Organica in laboratorio- Ed Piccin - Bologna
Assessment methods and Criteria
Two alternative assessment methods are available:
1. Continuous assessment (midterm exams)
This option includes two written midterm exams: one in the second half of April and the other at the end of the course. Each exam consists of 10 exercises aimed at the practical application of the theoretical concepts covered in class, to be completed within a maximum of two hours. Each exercise is graded on a scale from 0 to 3 points.
Admission to the second exam requires a minimum score of 17/30 in the first. If the student chooses to take the midterm exams, the grade for the written exam will be calculated as the average of the marks obtained in the two midterm tests.
2. Final exam
This option consists of a written exam lasting two hours, composed of 10 exercises, each graded from 0 to 3 points.
Admission to the written exam, as well as to the second midterm exam, is granted only to students who have submitted the laboratory report by the deadline indicated by the teacher and have successfully passed the General Chemistry exam.
The final grade will also consider the quality of the laboratory activities and the submitted reports, and will be calculated as a weighted average based on the credits assigned to the theoretical component (6 CFU) and the laboratory component (2 CFU).
1. Continuous assessment (midterm exams)
This option includes two written midterm exams: one in the second half of April and the other at the end of the course. Each exam consists of 10 exercises aimed at the practical application of the theoretical concepts covered in class, to be completed within a maximum of two hours. Each exercise is graded on a scale from 0 to 3 points.
Admission to the second exam requires a minimum score of 17/30 in the first. If the student chooses to take the midterm exams, the grade for the written exam will be calculated as the average of the marks obtained in the two midterm tests.
2. Final exam
This option consists of a written exam lasting two hours, composed of 10 exercises, each graded from 0 to 3 points.
Admission to the written exam, as well as to the second midterm exam, is granted only to students who have submitted the laboratory report by the deadline indicated by the teacher and have successfully passed the General Chemistry exam.
The final grade will also consider the quality of the laboratory activities and the submitted reports, and will be calculated as a weighted average based on the credits assigned to the theoretical component (6 CFU) and the laboratory component (2 CFU).
CHEM-05/A - Organic Chemistry - University credits: 8
Exercises: 16 hours
Tutorials: 32 hours
Lessons: 40 hours
Tutorials: 32 hours
Lessons: 40 hours
Professor:
Pini Elena Renata Elvira
Professor(s)
Reception:
By appointment
Via Golgi 19. Building 25010-Entrance C, IV floor