ORGANIC CHEMISTRY

Course objectives

Expected learning outcomes Organic chemistry is a chemistry discipline involving the scientific study of the structure, reactivity, properties and applications of compounds which are formed mainly by carbon atoms, forming covalent bonds, both from natural and artificial sources The general objective, is to provide students with the knowledge and competences necessary to understand the structure, reactivity and synthetic methods of different functional groups, and the mechanisms of organic reactions. For a Natural Science student, this learning is essential, to understand physical or macroscopic properties of matter on molecular basis and to know the role and impact of organic chemistry in natural sciences, modern technology and society. This knowledge will allow the student to be able to understand biochemistry, genetics and physiology, crucial topics in different next courses. Dublin Descriptors The Organic Chemistry course is devoted to provide students with the adequate knowledge to be independent in solving the examination problems or exercises. This ability will be acquired by the means of frontal lesson and guided exercitations that will be organized in ascending order of the difficulties they pose. Teaching materials, available on line will support students during the lessons even though studying the recommended text book is essential to acquire the skills and the competence that are necessary to perform the final exam. In order to improve the exposure ability, students will be constantly encouraged to communicate their ideas to both specialists and non specialists audiences. The Erasmus programme will enable students to improve their communications skills, by exchanging informations, problems and solutions. The specific objectives consist in acquiring the following knowledge and expertise: 1) to understand the importance of stereochemistry on the reactivity of organic compounds; 2) to understand the relationship between structure and reactivity for the different functional groups; 3) to acquire the basic knowledge of organic chemistry in order to understand the basic mechanism of organic reactions. 4) to acquire the basic knowledge of the organic synthesis 5) to apply the main concepts of stereochemistry to the reactivity of organic compounds. 6) to predict the reactivity and the physical properties of organic compounds. 7) to speculate about mechanistic aspect of the organic reactions. 8) to design the synthesis of organic molecules through their retrosynthetic analysis.

Channel 1
PAOLO LUPATTELLI Lecturers' profile

Program - Frequency - Exams

Course program
Arrhenius, Lowry-Brönsted e, and Lewis acids and bases. Factors influencing the strength of Lowry-Brönsted acids and bases: hybridization, polarizability, electronegativity, inductive effect, field effect, resonance, hydrogen bond, solvent. Alkanes and cycloalkanes Nomenclature, hybridization, structure, physical properties, structural isomers, conformation (torsional strain, angle strain), hybridization and bond angle (cyclopropane). Newman projections. Haworth projections. Reactivity: oxidation and radical halogenation [mention]. Alkenes Nomenclature, hybridization, structure, stability, physical properties, geometric isomerism, E-Z rules. Reactivity: addition of HX (X = halogens) [ionic (carbocations: structure, stability)], water, halogens, epoxidation (reaction with peracids), palladium-catalyzed hydrogenation and hydrogenation heats, Alkynes Nomenclature, hybridization, structure, physical properties. Reactivity: palladium-catalyzed addition of hydrogen (mention), addition of HX (X = halogen) (vinylic cations: hybridization, stability), addition of halogens, addition of water (catalyzed by sulfuric acid and Hg(II) salts), acidity of terminal alkynes (addition and nucleohilic substitution reactions of acetylides). Fundamentals of stereochemistry Stereoisomers. Chirality. Chiral and stereogenic center. Enantiomers and diastereoisomers. Symmetry elements: center, axis, plane. Enantiomers: nomenclature (Cahn, Ingold, and Prelog priority rules). Optical rotation. Racemates. Specific rotation. Enantiomeric excess. Compounds containing more than one chiral center (diastereoisomers and meso isomers). Fischer projections. Alkyl halides Structure and IUPAC nomenclature, physical properties. Nucleophilic substitution (SN), nucleophilicity and basicity. SN1: mechanism, stereochemistry, ion pairs, factors influencing the SN1 reaction (alkyl halide, leaving group, nucleophile, solvent (protic solvents, polar aprotic solvents, apolar aprotic solvents). SN2: mechanism, stereochemistry, factors influencing the SN2 reaction (alkyl halide, leaving group, nucleophile, solvent). SN1 vs SN2 (influence of the alkyl group, solvent, and nucleophile). beta-Elimination (E). E1: mechanism, regiochemistry (Saitseff’s rule). E2: mechanism, regiochemistry, stereochemistry.. E1 vs E2: influence of the alkyl halide, solvent, and base. SN1 vs E1 and SN2 vs E2 Formation of alkylmagnesium compounds. Alcohols Nomenclature, physical properties. Reactivity: acidity, synthesis of esters, alkyl halides, tosylates, oxidation (mechanism with chromic acid and pyridinium chlorochromate). Ethers and epoxides Nomenclature, physical properties. Reactivity: reaction with con HX (X = halogens). Epoxides: nomenclature, ring opening (acid-catalyzed, with nucleophiles). Aldehydes and ketones Nomenclature, physical properties. Addition reactions: reaction with boron and aluminum hydrides, with terminal alkynes, Grignard reagents, HCN, water, alcohols (acetals as protecting groups). Addition-elimination reactions: reaction with primary and secondary amines. Carboxylic acids Nomenclature, physical properties. Reactivity: acid-base reactions, reactions with LiAlH4, with alcohols, with SOCl2, with PBr3 (mention). Carboxylic acid derivatives Acyl halides, anhydrides, esters, lactones, amides, lactames, imides, nitriles: Nomenclature, physical properties. Reactivity: reaction with water [acyl chlorides, anhydrides, esters, (esters from 1°, 2°, and 3° alcohols), amides, nitriles], with alcohols (acyl chlorides, anhydrides, esters), (acyl chlorides), with ammonia and amines [acyl chlorides, anhydrides, esters], with Grignard reagents (esters), with LiAlH4 (esters, amides). Enols and enolates Keto-enol tautomerism (acid- and base-catalyzed), factors influencing the keto-enol equilibrium (hydrogen bond, resonance), Aldol condensation, Aldol condensation-dehydration (under acid and basic conditions), crossed aldol condensation. Aromatic compounds Aromaticity. Huckel rule. Aromatic, antiaromatic and non aromatic compounds. Aromatic ions. Heteroaromatics. Nomenclature. Electrophilic aromatic substitution: mechanism, substituent effects, halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation. Phenols Nomenclature. Reactivity: acidity, synthesis of esters and ethers. Amines Nomenclature. Chirality. Pyramidal inversion. Chirality of armonium salts. Reactivity: basicity of aliphatic and aromatic amines. Carbohydrates and amino acids: structure and general properties
Prerequisites
Students are expected to have basic knowledge of General and Inorganic Chemistry; in particular the following fundamentals of chemistry must be known: hybridization, resonance, fundamentals of thermodinamics (entalpy, Gibbs energy, entropy), chemical equilibria, fundamentals of chemical kinetics, reaction rate, transition state
Books
B. Botta ”Chimica Organica” Edi-Ermes, 2011 W. H. Brown ”Chimica Organica” Ed. Edises 2010 J. Mc Murry ”Chimica Organica” 8Ed. Ed. Piccin 2012 T.W.G. Solomons, C.B. Fryhle ”Chimica Organica” Ed. Zanichelli 2008
Frequency
The participation at the lectures is voluntary but highly recommended
Exam mode
The written test is evaluated on the capacity of the student to apply the fundamental principles of structure and reactivity of organic compounds for the resolution of problems. The oral test is evaluated on the capacity of the student to clearly explain basic principles of organic chemistry and to connect the different topics developed during the course.
Lesson mode
The course is given by classical lectures (frontal teaching) with the aid of blackboard and Power Point presentations
  • Lesson code97566
  • Academic year2024/2025
  • CourseNatural Sciences
  • CurriculumSingle curriculum
  • Year2nd year
  • Semester1st semester
  • SSDCHIM/06
  • CFU6
  • Subject areaDiscipline chimiche