Organic Chemistry
A.Y. 2024/2025
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 references to environmental issues. The learning of the concepts and notions acquired, will be facilitated by synchronous classroom and self-assessment exercises on digital platforms. Explanatory videos will also be made available to facilitate learning of more complex mechanisms. The course also includes a laboratory experiences in which experiments will be carried out in order to acquire the ability for the correct execution of an organic chemistry experiment, including the basic safety rules regarding the handling and the disposal of organic substances. The laboratory experiments aim to give the basic knowledge of the fundamental purification techniques (crystallization, distillation and chromatography), the separation (extraction) and the reactivity of organic compounds.
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 pi-greed 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 lecturer during the course of the exercises. In addition, periodic verification of understanding of the skills acquired will be possible through the performance of exercises chosen by the lecturer, 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, including through informing reports of laboratory experiences. (Dublin Descriptor 4: Ability to communicate what has been learned.)
By the end of the teaching, the student will have acquired the foundation for learning the preparatory topics for the Environmental Chemistry, Biochemistry, Food Chemistry and Chemical Toxicological Analysis teachings in subsequent years. (Dublin Descriptor 5: Ability to pursue study independently)
Attendance in the laboratory will enable the student to be able to perform standard laboratory procedures and use the necessary instrumentation for synthesis.
He/she will know how to apply the concepts of hybridization, covalent, polar, sigma and pi-greed 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 lecturer during the course of the exercises. In addition, periodic verification of understanding of the skills acquired will be possible through the performance of exercises chosen by the lecturer, 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, including through informing reports of laboratory experiences. (Dublin Descriptor 4: Ability to communicate what has been learned.)
By the end of the teaching, the student will have acquired the foundation for learning the preparatory topics for the Environmental Chemistry, Biochemistry, Food Chemistry and Chemical Toxicological Analysis teachings in subsequent years. (Dublin Descriptor 5: Ability to pursue study independently)
Attendance in the laboratory will enable the student to be able to perform standard laboratory procedures and use the necessary instrumentation for synthesis.
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: Chemical bonding and structure: Electronic configuration and hybridization of carbon atom. Ionic and covalent bonds; polarity. Intermolecular interactions. Structures and formulas of organic molecules. The organic reactions. Main types of organic reactions: mechanisms and intermediates involved. Acid-base equilibria. Radical and ionic reactions.
IUPAC nomenclature. Functional groups in organic chemistry.
HYDROCARBONS: alkanes, alkenes and alkynes Physical properties, reactivity, preparation methods. Conformational analysis of linear and cyclic alkanes. Newman projections. Substituted cycloalkanes: steric implications and cis-trans isomers, E/Z.
Types of organic reactions: addition, elimination, substitution, transposition. Reaction mechanisms: radical reactions and polar reactions. Double and triple bond electrophilic addition reactions: Markovnikov's rule. Addition of water, halogen acids, halogen and hypohalogen acids, Hydrogenation. Oxidation and hydroxylation.
STEREOCHEMISTRY: Geometry of carbon-containing compounds. Representation of molecules. Structural isomers. Chirality and stereogenicity. Fischer projections. Enantiomers, diastereoisomers and mesoforms. Optical activity and polarimetry. Resolution of racemes. Cahn/Ingold/Prelog nomenclature. Chirality of atoms other than carbon.
ALKYL HALIDES: Chemical and physical properties. Halogenated compounds and CFC.SN1 and SN2 Nucleophilic Substitution Reactions; mechanism and stereochemical consequences. Carbocation: stability and rearrangement. Elimination reactions. E1 and E2 reactions. Factors influencing the reaction mechanism. Competition between substitution and elimination.
ALCOHOLS, THIOLS, ETHERS. Alcohols as acids and bases. Reactivity. Oxidations. Oxidation of thiols. Synthesis and reactivity of ethers.
ORGANOMETALLIC COMPOUNDS: Grignard reagents. Reaction with carbonyl compounds.
CRBONYL GROUP: ALDEHYDES AND KETONES. structure of carbonyl group. Reactions of nucleophilic additions: addition of water, alcohol, amines. Oxidations and reductions. Aldol condensation.
CARBOXYLIC ACIDS AND DERIVATIVES. Reactivity: nucleophilic acyl substitution. Esters, anhydrides, acid chlorides, amides, nitriles: hydrolysis, reduction and synthesis.
ALKYLAMINES. Basicity and reactivity. Synthesis of nitrosoamines.
BENZENE: structure, Resonance energy. Huckel rule. Reactivity of benzene
PHENOL AND ANILINE: nomenclature, Acidity and basicity. Reactivity. Reaction with nitrous acid.
HETEROAROMATIC COMPOUNDS: nomenclature and reactivity in electrophilic substitution.
PHOSPHORUS DERIVATIVES: Classification, hydrolysis and biologic rule.
CARBONIC ACID DERIVATIVES: Urea, carbammates.
CARBOHYDRATES: Classification according to structure, C atoms, carbonyl group.
Stereochemistry: epimers. Hemiacetal structures: anomers and Haworth projections. Mutarotation.
Monosaccharide reactions: glycosidation; oxidation and reduction reactions.
Disaccharides and polysaccharides.
AMMINOACIDS: Classification. Stereochemistry. Acid/base properties: isoelectric point.
Alpha aminoacids reactivity: esterification; acylation; oxidation of cysteine; reaction with ninhydrin. Peptides and peptide bonding.
POLYMERS: Classifications. 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.
IUPAC nomenclature. Functional groups in organic chemistry.
HYDROCARBONS: alkanes, alkenes and alkynes Physical properties, reactivity, preparation methods. Conformational analysis of linear and cyclic alkanes. Newman projections. Substituted cycloalkanes: steric implications and cis-trans isomers, E/Z.
Types of organic reactions: addition, elimination, substitution, transposition. Reaction mechanisms: radical reactions and polar reactions. Double and triple bond electrophilic addition reactions: Markovnikov's rule. Addition of water, halogen acids, halogen and hypohalogen acids, Hydrogenation. Oxidation and hydroxylation.
STEREOCHEMISTRY: Geometry of carbon-containing compounds. Representation of molecules. Structural isomers. Chirality and stereogenicity. Fischer projections. Enantiomers, diastereoisomers and mesoforms. Optical activity and polarimetry. Resolution of racemes. Cahn/Ingold/Prelog nomenclature. Chirality of atoms other than carbon.
ALKYL HALIDES: Chemical and physical properties. Halogenated compounds and CFC.SN1 and SN2 Nucleophilic Substitution Reactions; mechanism and stereochemical consequences. Carbocation: stability and rearrangement. Elimination reactions. E1 and E2 reactions. Factors influencing the reaction mechanism. Competition between substitution and elimination.
ALCOHOLS, THIOLS, ETHERS. Alcohols as acids and bases. Reactivity. Oxidations. Oxidation of thiols. Synthesis and reactivity of ethers.
ORGANOMETALLIC COMPOUNDS: Grignard reagents. Reaction with carbonyl compounds.
CRBONYL GROUP: ALDEHYDES AND KETONES. structure of carbonyl group. Reactions of nucleophilic additions: addition of water, alcohol, amines. Oxidations and reductions. Aldol condensation.
CARBOXYLIC ACIDS AND DERIVATIVES. Reactivity: nucleophilic acyl substitution. Esters, anhydrides, acid chlorides, amides, nitriles: hydrolysis, reduction and synthesis.
ALKYLAMINES. Basicity and reactivity. Synthesis of nitrosoamines.
BENZENE: structure, Resonance energy. Huckel rule. Reactivity of benzene
PHENOL AND ANILINE: nomenclature, Acidity and basicity. Reactivity. Reaction with nitrous acid.
HETEROAROMATIC COMPOUNDS: nomenclature and reactivity in electrophilic substitution.
PHOSPHORUS DERIVATIVES: Classification, hydrolysis and biologic rule.
CARBONIC ACID DERIVATIVES: Urea, carbammates.
CARBOHYDRATES: Classification according to structure, C atoms, carbonyl group.
Stereochemistry: epimers. Hemiacetal structures: anomers and Haworth projections. Mutarotation.
Monosaccharide reactions: glycosidation; oxidation and reduction reactions.
Disaccharides and polysaccharides.
AMMINOACIDS: Classification. Stereochemistry. Acid/base properties: isoelectric point.
Alpha aminoacids reactivity: esterification; acylation; oxidation of cysteine; reaction with ninhydrin. Peptides and peptide bonding.
POLYMERS: Classifications. 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). 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, T. Poon - Introduzione alla Chimica Organica - quinta ed., 2014 - Ed. Edises, Napoli
· J. McMurry Fondamenti di Chimica Organica - quarta edizione - Ed. Zanichelli
· D. Klein Fondamenti di Chimica Organica - Ed Pearson
· M. S. Erickson " Guida alla soluzione dei problemi" da "Introduzione alla Chimica Organica" quinta ed., 2006 - Ed. Edises, Napoli
· Chimica organica. Esercizi risolti di chimica organica. Con Contenuto digitale (
· H. Hart, L. Craine, D. Hart "Chimica Organica" sesta ed- Ed. Zanichelli, Bologna
· Slides available on the teacher's Ariel website
For insights:
· J. McMurry "Chimica Organica" nona ed., 2017, Ed. Piccin, Padova.
· K. P. C. Vollhardt, "Chimica Organica" quarta edizione, 2016 - Ed. Zanichelli,
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, T. Poon - Introduzione alla Chimica Organica - quinta ed., 2014 - Ed. Edises, Napoli
· J. McMurry Fondamenti di Chimica Organica - quarta edizione - Ed. Zanichelli
· D. Klein Fondamenti di Chimica Organica - Ed Pearson
· M. S. Erickson " Guida alla soluzione dei problemi" da "Introduzione alla Chimica Organica" quinta ed., 2006 - Ed. Edises, Napoli
· Chimica organica. Esercizi risolti di chimica organica. Con Contenuto digitale (
· H. Hart, L. Craine, D. Hart "Chimica Organica" sesta ed- Ed. Zanichelli, Bologna
· Slides available on the teacher's Ariel website
For insights:
· J. McMurry "Chimica Organica" nona ed., 2017, Ed. Piccin, Padova.
· K. P. C. Vollhardt, "Chimica Organica" quarta edizione, 2016 - Ed. Zanichelli,
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
The exam consists of a written test lasting two hours, which aims to verify through the answer to 10 questions/exercises, the achievement of the following educational objectives: (i) knowledge of the fundamental concepts necessary for an understanding of the structure and the reactivity of organic molecules. (ii) ability to use the concepts acquired, to solve problems of reactivity and structure. Each correct exercise allows the acquisition of a score between zero and three points. Passing the written test, is achieved upon overall achievement of at least 18 points.
The student is admitted to the written exam only if he has previously delivered the Laboratory Report.
The Laboratory Report together with the laboratory quality activity, will be included in the final evaluation (weighted average).
The student is admitted to the written exam only if he has previously delivered the Laboratory Report.
The Laboratory Report together with the laboratory quality activity, will be included in the final evaluation (weighted average).
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Lessons: 40 hours
Single bench laboratory practical: 32 hours
Lessons: 40 hours
Professor:
Pini Elena Renata Elvira
Professor(s)
Reception:
By appointment
Via Golgi 19. Building 25010-Entrance C, IV floor