Catalogo dei Corsi di studio

Knowledge and understanding
At the end of the course the student knows the main concepts of organic chemistry needed both for the knowledge of the molecular structure and for the understanding of the reactivity of the main functional groups. Moreover, he learns the basic concepts of stereochemistry and reaction mechanisms in organic chemistry.
Applying knowledge and understanding
At the end of the course the student knows and understands the spatial arrangement of the carbon structures and knows how to assign the name to the simplest molecules according to the IUPAC nomenclature; he is able to graphically represent the structures through the most commonly used conventions and assign the absolute configuration to the stereocenters. Furthermore, the student knows the reactivity of the functional groups according to the general scheme of the main reaction mechanisms.
Making judgements
At the end of the course the student is able to collect and understand information useful to express a proper independent opinion. In particular, he must show a critical and proposing spirit in the discussion of issues inherent to organic molecules and biologically active compounds.
Communication skills
At the end of the course the student has the ability to communicate outward the knowledge he has learned during the course, both toward the scientific community and the labor market. In particular, he must be able to provide clear and direct information on chemical reactivity, with particular emphasis to that of the biologically active compounds.
Learning skills
Given the basic training activity of this course, the student who has passed the exam is able to undertake the study of the other basic and characterizing training activities that have been set in the Master degree, as Biochemistry and Molecular Biology.

Programme

Structure and chemical bonds of atoms and molecules. Electronegativity and polarity of the bond. Lewis structures. Carbon hybridization: ethane, ethylene, acetylene. Bond length and bond strength. The shape of the molecules. Resonance. Representation of organic structures. The curved arrow convention [2 hours].

Acids and bases by Brønsted-Lowry and Lewis. Factors that affect acidity. Acid strength and pKa. Prediction of equilibrium [2 hours].

Main functional groups. Structural and electronic features [2 hours].

Alkanes and cycloalkanes. IUPAC nomenclature. Common names. Conformation of acyclic alkanes (ethane, butane). Cycloalkanes. Cyclohexane (chair conformation). Cis/trans isomerism in cyclohexanes substituted (mono- and di-substituted) [2 hours].

Alkenes. IUPAC nomenclature (use of cis/trans and E/Z convention). Electrophilic addition reactions: hydrohalogenation (Markovnikov’s rule, stereochemistry); hydration; halogenation (stereochemistry), hydrogenation. Carbocations and their stability. Reaction of 1,2-dihydroxylation [3 x 2 hours].

Alkynes. IUPAC nomenclature. Physical properties. Reactivity: acidity of terminal alkynes. Reactions of the acetylide anions. Dienes and conjugated dienes: 1,3-butadiene. Delocalization of electrons, hybridization and geometry [2 hours].

Stereochemistry. The two main classes of isomers. Chiral and achiral molecules. Stereogenic centers. Absolute R/S configuration. Diastereoisomers. Compounds with two or more stereogenic centers. Mesoforms and racemic mixtures. Physical properties of enantiomers (optical activity, specific rotation, enantiomeric excess) and diastereoisomers. Chemical properties of enantiomers [2 x 2 hours].

Type of organic reactions (substitution, elimination, addition) and mechanisms. Cleavage and formation of bonds (radicals, carbocations, carbanions). Thermodynamics (equilibrium constant and free energy changes). Nucleophiles and electrophiles [concepts given during the different lessons].

Alkyl halides. IUPAC nomenclature. Physical properties. Polarity of the carbon-halogen bond. Nucleophilic substitution (halide, leaving group, nucleophile, solvent effect). SN2 and SN1 mechanism (kinetics, stereochemistry, nature of the halide, solvent effect). Stability of carbocations. Factors determining the SN2 or SN1 mechanism. General features of beta-elimination. E2 and E1 Elimination mechanism (kinetics, nature of halide). Zaitsev’s rule (regioselective and stereoselective reactions). Factors determining the E2 or E1 mechanism [3 x 2 hours].

Alcohols, ethers and thiols. Structure, IUPAC nomenclature, physical properties. Reactivity of alcohols: dehydration, reaction with halogenidric acids. Epoxides. Phenols and their acidity [2 x 2 hours].

Benzene and aromatic compounds. The structure of benzene. Nomenclature. Stability of benzene. Hückel's rule. Electrophilic aromatic substitution (SEAr) reaction: general mechanism. Benzene halogenations (mechanism), nitration and sulphonation. Friedel-Crafts alkylation and acylation. Aromatic electrophilic substitution on substituted benzenes (effect of substituents on reactivity and orientation). Polycyclic aromatic hydrocarbons [2 x 2 hours].

Aldehydes and ketones. Structure, IUPAC nomenclature. Reactivity of the carbonyl group. Nucleophilic addition reaction (general mechanism). Carbon nucleophiles (hydrogen cyanide and Grignard reagents); oxygen nucleophiles (water and alcohols); nitrogen nucleophiles (ammonia and derivatives, primary amines). Acidity of alpha hydrogens. Keto-enol tautomerism. Aldol reactions (mechanism) [2 x 2 hours].

Carboxylic acids. Structure, IUPAC nomenclature, acidity. Derivatives of carboxylic acids: acyl chlorides, anhydrides, esters, amides. Esterification of Fischer and alkaline hydrolysis of esters. Structure of the amide bond [2 hours].

Adopted texts

Autori Vari, Chimica Organica Essenziale, Edi-Ermes, Milano, 2018, 2° edizione (a cura di Bruno Botta).
John McMurry, Fondamenti di Chimica Organica, Zanichelli, Bologna, 2005.
William H. Brown, Thomas Poon, Introduzione alla Chimica Organica, EdiSES S.r.l., Napoli, III Ed.

Prerequisites

Given the basic training activity of this course, it is useful that the students attend and learn the concepts of general and inorganic chemistry presented during the same teaching semester.

Frequency modes

The frequency of the course is optional, but strongly recommended.

Exam modes

The Organic Chemistry exam, divided into two Modules, consists of a written test (related to Module 1, first semester) that serves for the admission to the oral exam (related to Module 2, second semester). The written test (lasting 1 hour) is not given a mark, but it is only an admission (ADMITTED/NOT ALLOWED) to the oral exam. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade. While access to the written test is possible from the first exam session (in January and February), it is necessary to wait until the end of the second semester for the oral exam (the first possible date is June).

To access the written exam, students must register on the E-learning platform.

The written test (which lasts for one calendar year) is structured in 6 open-ended exercises, and may also contain a theoretical question on a reaction mechanism proposed in class.

To access the oral exam, students must register on the INFOSTUD platform.

The oral exam consists of 3 questions on the Module 2 program (average exam duration: 30 minutes). To achieve a score of 30/30 cum laude, the student must demonstrate that he has acquired excellent knowledge of all the topics covered during the course, showing a natural ability to quickly link between them.

Exam reservation date start	Exam reservation date end	Exam date
28/01/2020	03/02/2020	04/02/2020
14/02/2020	20/02/2020	21/02/2020
05/06/2020	15/06/2020	25/06/2020
20/06/2020	10/07/2020	16/07/2020
17/07/2020	18/07/2020	20/07/2020
17/09/2020	23/09/2020	24/09/2020
16/11/2020	19/11/2020	20/11/2020