Catalogo dei Corsi di studio

Knowledge and understanding
At the end of 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, the student learns the basic concepts of stereochemistry and reaction mechanisms in organic chemistry.

Applying knowledge and understanding
At the end of course, the student knows and understand the spatial arrangement of the carbon structures and knows how to assign the name to the simplest molecules according to the IUPAC nomenclature; the student is able to graphically show 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
The student, at the end of course, 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 natural products and their implications in global health.

Communication skills
The student, at the end of course, has the ability to communicate outward the knowledge he has learned during the Master degree, 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 natural products.

Learning skills
Given the basic training activity of this course, students who have passed the exam are able to undertake the study of other basic and characterizing training activities that have been set in the Master degree.

Programme

Structure and bonding. The periodic table. Bonding. Lewis structures. Resonance. Determining molecular shape. Drawing organic structures. Hybridization. Ethane, ethylene, acetylene. Electronegativity and bond polarity. Polarity of molecules.
Acids and bases. Brønsted-Lowry acids and bases. Reactions of Brønsted-Lowry acids and bases. Acid strength and pKa. Predicting the outcome of acid-base reactions. Factors that determine acid strength. Lewis acids and bases.
Organic molecules and functional groups. Functional groups. Intermolecular forces. Physical properties. Functional group and reactivity.
Alkanes and cycloalkanes. Introduction. Nomenclature for alkanes and cycloalkanes. Common names. Physical properties. Conformations of cyclic alkanes (ethane, butane). Cycloalkanes. Cyclohexane. Substituted cycloalkanes. Oxidation of alkanes.
Stereochemistry. The two major classes of isomers. Chiral and achiral molecules. Stereogenic centers. Labeling stereogenic centers with R/S. Diastereomers. Compounds with two or more stereogenic centers. Meso compounds. Physical properties of stereoisomers. Chemical properties of enantiomers.
Organic reactions. Equations for organic reactions. Kinds of organic reactions. Bond breaking and bond making. Bond dissociation energy. Thermodynamics. Enthalpy and entropy. Energy diagrams. Kinetics. Catalysts.
Alkyl halides and Nucleophilic Substitution. Introduction. Nomenclature. Physical properties. The polar C-halogen bond. Nucleophilic substitution (effect of halide, of leaving group, of nucleophile, of solvent). SN2 and SN1 Mechanisms (kinetics, stereochemistry, effect of halide, of solvent). Carbocation stability. SN2 versus SN1. Vinyl halides and aryl halides.
Alkyl halides and elimination reactions. General features of elimination. Alkenes (C=C bond, cis/trans isomers, stability). E2 and E1 elimination mechanisms (kinetics, halide). Zaitsev rule (regio and steroselectivity). E2 versus E1. E2 reactions and alkyne synthesis. Substitution versus elimination.
Alcohols, ethers and epoxides. Structure, Nomenclature. Physical properties. Preparations. Reactivity of alcohols: dehydration, reaction with HX. Reaction of ethers with strong acid. Reactions of epoxides with nucleophiles and acids.
Alkenes. Nomenclature (cis/trans and E/Z). Physical properties. Preparation of alkenes. Addition reactions: hydrohalogenation (Markovnikov’s rule, stereochemistry); hydration; halogenation (stereochemistry).
Alkynes. Nomenclature. Physical properties. Preparations. Reactivity: terminal alkynes as acids; hydrohalogenation; halogenation; hydration (keto-enol tautomerism). Reaction of acetylide anions.
Oxidation and reduction. Reducing agents. Reduction of alkenes and of alkynes. Oxidizing agents. Epoxidation, dihydroxylation, oxidative cleavage of alkenes and alkynes. Oxidation of alcohols.
Radical reactions. Introduction. General features. Halogenation of alkanes: mechanism. Radical addiction to double bonds.
Conjugation, resonance and dienes. Conjugation. Resonance and allylic carbocations. The resonance hybrid. Electron delocalization, hybridization and geometry. Conjugated dienes. 1,2 and 1,4 electrophilic addiction. Kinetic versus thermodynamic products.
Benzene and aromatic compound. The structure of benzene. Nomenclature. Benzene’s stability. Hückel’s rule. Polycyclic aromatic compounds. Aromatic heterocyclic compounds (pyridine, pyrrole). Ionic aromatic compounds (cyclopentadienyl anion and tropylium cation).
Electrophilic aromatic substitution. The general mechanism. Halogenation. Nitration and sulfonation. Friedel-Crafts alkylation and acylation. Electrophilic aromatic substitution of substituted benzenes (substituent effects on velocity and on orientation).
Amines. Structure and bonding. Nomenclature. Preparation by direct nucleophilic substitution, by reduction of nitrogen containing functional groups (reductive amination).
Introduction to carbonyl chemistry; organometallic reagents; oxidation and reduction. General reactions of carbonyl compounds: nucleophilic addition to aldehydes and ketones, nucleophilic substitution of RCOZ. Reduction of aldehydes and ketones (stereochemistry). Reduction of carboxylic acids and their derivatives. Oxidation of aldehydes. Organometallic reagents of lithium, magnesium and copper; reactions with aldehydes and ketones and with carboxylic acid derivatives. α,β-unsatured carbonyl compounds: 1,2- and 1,4-addition.
Aldehydes and ketones –Nucleophilic addition. Nomenclature. Preparation. Reactivity: nucleophilic addition of H- and R-, of -CN, of 1y and 2y amines, of H2O, of alcohols (acetals). Cyclic hemiacetals.
Carboxylic acids and the acidity of the O-H bond. Structure and nomenclature. Preparation. Acidity. Inductive effects in aliphatic and aromatic acids. Substituted benzoic acids. Sulfonic acids.
Carboxylic acids and their derivatives – Nucleophilic acyl substitution. Structure and bonding. Nomenclature. Nucleophilic acyl substitution: reaction of acid chlorides, of anhydrides, of carboxylic acids, of esters, of amides.
Substitution reactions of carbonyl compound in enols and enolates. Direct enolate alkylation. Malonic ester synthesis. Acetoacetic ester synthesis.
Carbonyl condensation reactions. The aldol reaction. The Claisen reaction. The Michael reaction.
Secondary Metabolism: Introduction and classification of main pathways.

note: time spent for each issue is indicated in the Italian version.

Adopted texts

1- Gorzynski Smith J.: Fondamenti di Chimica Organica, McGrow-Hill, 2009. ISBN 978 88 386 6488-5.
2- Botta B., a cura di: Chimica Organica Essenziale, Edi-Ermes, 2012. ISBN 978-88-08-7051-354-7.
3- Paul M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali (II ed. Italiana), Piccin. ISBN: 978-88-299-2234-5

Prerequisites

For an easy approach to the course, it is advisable to have acquired the knowledge of general chemistry.

Study modes

Blendeed lessons using Prodigit system

Frequency modes

Attendance at course is not mandatory, however it is highly encouraged the frequency of lessons for a better understanding of the topics. For an easy understanding of the topics covered in the course it is recommended to have passed the General and Inorganic Chemistry exam.

Exam modes

The exam consists of a written test (lasting one hour) that serves for admission to the oral exam, followed by the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade.

The written test consists in 12-15 exercises, which may also contain practical or theoretical questions on the whole program. The student will attend the oral exam if he reaches the status of “ammesso”.

To access the written exam, students must register on the E-learning platform. The written test lasts only one session namely January/February, June/July, September, and November.


The oral exam consists of 3 questions on the whole 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 link between them quickly.
To access the oral exam, students must register on INFOSTUD.

Exam reservation date start	Exam reservation date end	Exam date
10/02/2023	20/02/2023	21/02/2023
10/02/2023	20/02/2023	21/02/2023
05/04/2023	15/04/2023	17/04/2023
05/04/2023	15/04/2023	17/04/2023
05/04/2023	15/04/2023	17/04/2023
14/06/2023	25/06/2023	27/06/2023
28/06/2023	12/07/2023	13/07/2023
07/09/2023	13/09/2023	14/09/2023
09/11/2023	14/11/2023	15/11/2023
11/01/2024	17/01/2024	18/01/2024

Programme

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

Acids and bases
Acids and bases by Brønsted-Lowry. Reactions of acids and bases by Brønsted-Lowry. Acid strength and pKa. Prediction of equilibrium. Factors that affect acidity. Acids and bases by Lewis. Functional groups. Intermolecular forces. Physical properties. Functional groups and reactivity [2 hours].

Alkanes and cycloalkanes
Introduction. IUPAC nomenclature for alkanes and cycloalkanes. Common names. Physical properties. Conformation of acyclic alkanes (ethane, butane). Cycloalkanes. Cyclohexane (chair conformation, ring inversion). Cyclohexanes substituted (mono- and di-substituted) [2 x 2 hours].

Alkenes
IUPAC nomenclature (use of cis/trans and E/Z convention). Physical properties. Preparation of alkenes. Electrophilic addition reactions: hydrohalogenation (Markovnikov’s rule, stereochemistry); hydration; halogenation (stereochemistry) [3 x 2 ore].

Alkynes
IUPAC nomenclature. Physical properties. Preparation. Reactivity: acidity of terminal alkynes; hydrohalogenation; halogenation; hydration. Reactions of the acetylide anions [2 hours].

Conjugation, resonance and dienes
Conjugation. Resonance and allylic carbocations. The resonance hybrid. Delocalization of electrons, hybridization and geometry. Conjugated dienes: 1,3-butadiene [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].

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

Alkyl halides and substitution reactions
Introduction. 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 [2 hours].

Alkyl halides and elimination reactions
General features of elimination. Alkenes (C=C double bond, cis/trans isomers, stability). E2 and E1 elimination mechanism (kinetics, nature of halide). Zaitsev’s rule (regioselective and stereoselective reactions). Factors determining the E2 or E1 mechanism [2 hours].

Alcohols, ethers and epoxides
Structure, IUPAC nomenclature, physical properties. Preparations. Reactivity of alcohols: dehydration, reaction with halogenidric acids. Reactivity of ethers with strong acids. Reaction of epoxides with nucleophiles and with acids [2 x 2 hours].

Benzene and aromatic compounds
The structure of benzene. Nomenclature. Stability of benzene. Hückel's rule. Polycyclic aromatic hydrocarbons. Aromatic heterocycles (pyridine, pyrrole) [2 hours].

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) [2 hours].

Amines
Structure, IUPAC nomenclature, physical properties. Preparation by direct nucleophilic substitution and by reduction of functional groups containing nitrogen; reductive amination [2 hours].

Adopted texts

One of the following books:

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

For the chemistry of natural products:
Paul M. Dewick, Chimica, Biosintesi e Bioattività delle Sostanze Naturali, Piccin-Nuova Libraria, 2012.

Prerequisites

For an easy understanding of the topics covered in the course it is recommended to have acquired the basics of general and inorganic chemistry.

Study modes

The course consists of frontal classes and numerical exercises on the blackboard that are intended to prepare students for the written test. During the lessons, the teacher stimulates the students with questions related to what it has just been presented, with the aim of making them participate and stimulate the study at home, lesson by lesson. Students are invited to read the various textbooks recommended at the beginning of the course and to find, on them, the discussion of the various topics proposed in class.

Frequency modes

Attendance to the course is not mandatory, but strongly recommended.

Exam modes

The exam consists of a written test (lasting 1 hour) that serves for the admission to the oral exam, followed by the oral test.
Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade.

The written test is structured in 12 open-ended exercises and may also contain a theoretical question on a reaction mechanism proposed in class. To access the written exam, students must register on the E-learning platform. The validity of the test is limited to one session only, namely January/February, June/July, September, November).

The oral exam consists of 3 questions on the whole 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. To access the oral exam, students must register on INFOSTUD.

Exam reservation date start	Exam reservation date end	Exam date
01/01/2022	22/01/2023	23/01/2023
01/02/2023	19/02/2023	20/02/2023
01/02/2023	19/02/2023	20/02/2023
02/03/2023	05/04/2023	06/04/2023
02/03/2023	05/04/2023	06/04/2023
01/06/2023	19/06/2023	20/06/2023
28/06/2023	09/07/2023	10/07/2023
01/09/2023	19/09/2023	20/09/2023

Programme

Reduction and oxidation. Reducing agents. Reduction of alkenes and alkynes. Oxidizing agents. Epoxidation, dihydroxylation, oxidative cleavage of alkenes and alkynes. Oxidation of alcohols.

Radicalic reaction. Introduction. General reactivity. Halogenation of alkanes: mechanism. Radicalic addition to double bonds.

Introduction to carbonyl group chemistry. General reactivity of carbonyl compounds.

Aldehydes and ketones. Nomenclature. Preparation. Reactivity: nucleophilic addition of water. Imine and enamine. Acetals and hemiacetals, cyclic hemiacetals. Reduction of aldehydes and ketones (with stereochemistry aspects). Organometallic reagents of lithium and magnesium (reactivity as bases and as nucleophiles). α,β-Unsaturated carbonyl compounds: addition 1,2 vs 1,4.

Carboxylic acids and the acidity of the O-H bond. Structure and nomenclature. Preparation. Acidity. Inductive effects in aliphatic and aromatic acids.

Carboxylic acids and derivatives – Nuclephilic acyl substitution. Structure and bonds. Nomenclature and main features of acyl chlorides, anhydrides, acids, esters and amides. Nuclephilic acyl substitution: reaction of acyl chlorides and esters.

Substitution reaction at the α – carbon of carbonyl compounds. Direct alkylation of enolates. Aldol condensation.

Introduction to Biomolecules. Carbohydrates. Peptides and proteins. Lipids. Nucleic acids.

Carbohydrates. Structure and classification (aldoses and ketoses). Fisher projections. Cyclic form of monosaccharides: glucose and fructose. Glycosides. Disaccharides. Polysaccharides.

Secondary metabolism. Introduction and classification of the main metabolic pathways. Enzymes and some examples of enzymatic reactions.

Terpenes and steroids. Structure and biosynthesis.

Alkaloids. Classification and examples.

Adopted texts

Chimica Organica Essenziale, Autori Vari (a cura di Bruno Botta), Edi-Ermes, Milano, 2° edizione, 2018.

Chimica, Biosintesi e Bioattività delle Sostanze Naturali, Paul M. Dewick, Piccin-Nuova Libraria, 2012 (per la parte di sostanze organiche naturali).

Prerequisites

It is strongly suggested a good knowledge of general and inorganic chemistry.

Study modes

The course consists of taught classes and numerical exercises on the interactive whiteboard that are intended to prepare students for the written test. During the lessons, the teacher stimulates the students with questions related to what it has just been presented, with the aim of making them participate and stimulate the study at home, lesson by lesson. Students are invited to read the various textbooks recommended at the beginning of the course and to find on them, the discussion of the various topics proposed in class.

Frequency modes

Attendance at course is not mandatory, however it is highly encouraged the frequency of lessons for a better understanding of the topics. For an easy understanding of the topics covered in the course it is recommended to have passed the General and Inorganic Chemistry exam.

Exam modes

The exam consists of a written test (lasting 1 hour) that serves for the admission to the oral exam, followed by the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade.

The written test consists in 12 exercises, which may also contains practical or theoretical questions on the whole program.

To access the written exam, students must register on the E-learning platform. The written test lasts only one session namely January/February, June/July, September, November.


The oral exam consists of 3 questions on the whole 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. To access the oral exam, students must register on INFOSTUD.

Programme

Part 2 (3CFU)

- Carboxylic acids and the acidity of the O-H bond. Structure and nomenclature. Preparation. Acidity. Inductive effects in aliphatic and aromatic acids. Substituted benzoic acids. Sulphonic acids.

- Carboxylic acids and derivatives – Nucleophilic acyl substitution. Structure and bonding. Nomenclature. Nucleophilic acyl substitution: reaction of acid chlorides and esters.

- Substitution reactions of carbonyl compound at the α- carbon: Enols and enolates. Direct enolate alkylation. Carbonyl condensation reactions. The aldol reaction.

- Introduction to Biomolecules. Carbohydrates. Peptides and proteins. Lipids. Nucleic acids.

- Carbohydrates. Structure. Classification (aldose e ketose). Fischer projection. Monosaccharides and cyclization: glucose and fructose. Glycosides. Disaccharides. Polysaccharides.

- Secondary Metabolism: Introduction and classification of main pathways. Enzymes and some enzymatic reactions.
- Terpenes e steroids: structure and introduction to the biosynthesis.

- Alkaloids: classifications.

-Autovalutazione

Adopted texts

1- Gorzynski Smith J.: Fondamenti di Chimica Organica, McGrow-Hill, 2009. ISBN 978 88 386 6488-5.
2- Botta B., a cura di: Chimica Organica Essenziale, Edi-Ermes, 2012. ISBN 978-88-08-7051-354-7.
3- Paul M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali (II ed. Italiana), Piccin. ISBN: 978-88-299-2234-5

Prerequisites

For an easy approach to the course, it is advisable to have acquired the knowledge of general chemistry.

Study modes

Blendeed lessons using Prodigit system

Frequency modes

Attendance at course is not mandatory, however it is highly encouraged the frequency of lessons for a better understanding of the topics. For an easy understanding of the topics covered in the course it is recommended to have passed the General and Inorganic Chemistry exam.

Exam modes

The exam consists of a written test (lasting one hour) that serves for admission to the oral exam, followed by the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade.

The written test consists in 12-15 exercises, which may also contain practical or theoretical questions on the whole program. The student will attend the oral exam if he reaches the status of “ammesso”.

To access the written exam, students must register on the E-learning platform. The written test lasts only one session namely January/February, June/July, September, and November.


The oral exam consists of 3 questions on the whole 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 link between them quickly.
To access the oral exam, students must register on INFOSTUD.

Exam reservation date start	Exam reservation date end	Exam date
10/02/2023	20/02/2023	21/02/2023
10/02/2023	20/02/2023	21/02/2023
05/04/2023	15/04/2023	17/04/2023
05/04/2023	15/04/2023	17/04/2023
05/04/2023	15/04/2023	17/04/2023
14/06/2023	25/06/2023	27/06/2023
28/06/2023	12/07/2023	13/07/2023
07/09/2023	13/09/2023	14/09/2023
09/11/2023	14/11/2023	15/11/2023
11/01/2024	17/01/2024	18/01/2024

Programme

Structure and bonding. The periodic table. Bonding. Lewis structures. Resonance. Determining molecular shape. Drawing organic structures. Hybridization. Ethane, ethylene, acetylene. Electronegativity and bond polarity. Polarity of molecules.

Acids and bases. Brønsted-Lowry acids and bases. Reactions of Brønsted-Lowry acids and bases. Acid strength and pKa. Predicting the outcome of acid-base reactions. Factors that determine acid strength. Lewis acids and bases. Organic molecules and functional groups. Functional groups. Intermolecular forces. Physical properties. Functional group and reactivity.

Alkanes and cycloalkanes. Introduction. Nomenclature for alkanes and cycloalkanes. Common names. Physical properties. Conformations of cyclic alkanes (ethane, butane). Cycloalkanes. Cyclohexane. Substituted cycloalkanes. Oxidation of alkanes.

Stereochemistry. The two major classes of isomers. Chiral and achiral molecules. Stereogenic centers. Labeling stereogenic centers with R/S. Diastereomers. Compounds with two or more stereogenic centers. Meso compounds. Physical properties of stereoisomers. Chemical properties of enantiomers.
Alkenes. Nomenclature (cis/trans and E/Z). Physical properties. Preparation of alkenes. Addition reactions: hydrohalogenation (Markovnikov’s rule, stereochemistry); hydration; halogenation (stereochemistry).

Alkynes. Nomenclature. Physical properties. Preparations. Reactivity: terminal alkynes as acids; hydrohalogenation; halogenation; hydration (keto-enol tautomerism). Reaction of acetylide anions.

Organic reactions. Equations for organic reactions. Kinds of organic reactions. Bond breaking and bond making. Bond dissociation energy. Thermodynamics. Enthalpy and entropy. Energy diagrams. Kinetics. Catalysts.

Alkyl halides and Nucleophilic Substitution. Introduction. Nomenclature. Physical properties. The polar C-halogen bond. Nucleophilic substitution (effect of halide, of leaving group, of nucleophile, of solvent). SN2 and SN1 Mechanisms (kinetics, stereochemistry, effect of halide, of solvent). Carbocation stability. SN2 versus SN1. Vinyl halides and aryl halides.

Alkyl halides and elimination reactions. General features of elimination. Alkenes (C=C bond, cis/trans isomers, stability). E2 and E1 elimination mechanisms (kinetics, halide). Zaitsev rule (regio and steroselectivity). E2 versus E1. E2 reactions and alkyne synthesis. Substitution versus elimination.

Alcohols, ethers and epoxides. Structure, Nomenclature. Physical properties. Preparations. Reactivity of alcohols: dehydration, reaction with HX. Reaction of ethers with strong acid. Reactions of epoxides with nucleophiles and acids.

Oxidation and reduction. Reducing agents. Reduction of alkenes and of alkynes. Oxidizing agents. Epoxidation, dihydroxylation, oxidative cleavage of alkenes and alkynes. Oxidation of alcohols.

Radical reactions. Introduction. General features. Halogenation of alkanes: mechanism. Radical addiction to double bonds.

Conjugation, resonance and dienes. Conjugation. Resonance and allylic carbocations. The resonance hybrid. Electron delocalization, hybridization and geometry. Conjugated dienes. 1,2 and 1,4 electrophilic addiction. Kinetic versus thermodynamic products.

Benzene and aromatic compound. The structure of benzene. Nomenclature. Benzene’s stability. Hückel’s rule. Polycyclic aromatic compounds. Aromatic etherocyclic compounds (pyridine, pyrrole). Ionic aromatic compounds (cyclopentadienyl anion and tropylium cation).

Electrophilic aromatic substitution. The general mechanism. Halogenation. Nitration. Friedel-Crafts alkylation and acylation. Electrophilic aromatic substitution of substituted benzenes (substituent effects on velocity and on orientation).

Amines. Structure and bonding. Nomenclature. Preparation by direct nucleophilic substitution, reductive amination.

Aldehydes and ketones –Nucleophilic addition. Nomenclature. Preparation. Reactivity: nucleophilic addition of H- and R-, of 1y and 2y amines, of H2O, of alcohols (acetals). Cyclic hemiacetals. Reduction of aldehydes and ketones (stereochemistry). Organometallic reagents of lithium, magnesium, and copper. α,β-unsatured carbonyl compounds: 1,2- and 1,4-addition.

Adopted texts

1- Gorzynski Smith J.: Fondamenti di Chimica Organica, McGrow-Hill, 2009. ISBN 978 88 386 6488-5.
2- Botta B., a cura di: Chimica Organica Essenziale, Edi-Ermes, 2012. ISBN 978-88-08-7051-354-7.
3- Paul M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali (II ed. Italiana), Piccin. ISBN: 978-88-299-2234-5

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, aromaticity, fundamentals of thermodinamics (entalpy, Gibbs energy, entropy), chemical equilibria, fundamentals of chemical kinetics, reaction rate, transition state.

Study modes

The course is provided through traditional lessons integrated with exercises. The lessons are held in classrooms where there are devices suitable for projecting the slides of the course, available to CTF students on the Sapienza E-learning platform. The exercises, provided throughout the course, cover all the topics covered during the theoretical lessons and prepare students for the written test. There are several summarizing sessions in which different quizzes that are representative of those given to the exam, are shown.

Frequency modes

Attendance of lectures and exercises, although very useful for achieving the course's educational objectives, is not mandatory.

Exam modes

The exam consists of a written test (lasting one hour) that serves for admission to the oral exam, followed by the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade.

The written test consists in 12-15 exercises, which may also contain practical or theoretical questions on the whole program. The student will attend the oral exam if he reaches the status of “ammesso”.

To access the written exam, students must register on the E-learning platform. The written test lasts only one session namely January/February, June/July, September, and November.


The oral exam consists of 3 questions on the whole 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 link between them quickly.
To access the oral exam, students must register on INFOSTUD.

Exam reservation date start	Exam reservation date end	Exam date
13/02/2023	20/02/2023	21/02/2023
05/04/2023	11/04/2023	13/04/2023
19/06/2023	26/06/2023	27/06/2023
06/07/2022	12/07/2023	13/07/2023
07/09/2023	12/09/2023	14/09/2023
09/11/2023	13/11/2023	15/11/2023
12/01/2024	16/01/2024	18/01/2024