The course is finilized to the acquisition of the theoretical and applied principles of organic chemistry. The primary objective of the course is to impart to students the language of organic chemistry, with particular reference to nomenclature (IUPA and common names), the physicochemical proprities of organic compounds and the structural characteristics of functional groups. In addition, knowledge of the main mechanisms of organic reactions and the reactivity of the most common functional groups will be conveyed. Emphasis will be placed on the main classes of organic compounds of biological significance: lipids, carbohydrates, amino acids and proteins, and nucleic acids.

1) Structure and bonding

Introduction to the course - Periodic table - Bonding - Lewis structures - Resonance - Shape of molecules - Representation of organic structures - Hybridization - Ethane, ethylene and acetylene - Bond length and bond strength - Electronegativity and bond polarity - Polarity of molecules

2) Acids and bases

Brønsted-Lowry acids and bases - Brønsted-Lowry acid and base reactions - Acid strength and pKa - Prediction of equilibrium in acid-base reactions - Factors determining acid strength - Lewis acids and bases

3) Introduction to organic molecules and functional groups

Review of functional groups - Intermolecular forces - Physical properties

4) Alkanes

IUPAC nomenclature - Common names - Physical properties of alkanes - Conformation of acyclic alkanes (Conformation of ethane; Conformation of butane) -- Conformation of cyclic alkanes (Conformation of cyclohexane) - Oxidation of alkanes

5) Stereochemistry.

Constitutional isomers and stereoisomers - Chiral and achiral molecules - Stereogenic centers - Naming stereogenic centers with R or S descriptors - Enantiomers - Diastereoisomers - Meso compounds - Optical activity of chiral compounds - The separation of enantiomers - Fischer projection formulas and relative D and L descriptors

6) Understanding Organic Reactions.

Types of organic reactions-Bond breaking and bond formation-Thermodynamics-Energy diagrams for single- and two-stage reaction mechanisms-Kinetics-The Hammond postulate-Catalysts

7) Alkyl halides and substitution reactions.

Structure - Nomenclature - Physical properties - General characteristics of nucleophilic substitution - Outgoing group - Nucleophilic - Possible mechanisms for nucleophilic substitution - SN2 mechanism - SN1 mechanism -Carbocation stability - When is a mechanism SN1 or SN2? - Vinyl halides and aryl halides

8) Alkyl halides and elimination reactions.

General features of elimination - Alkenes: the products of elimination reactions - Mechanism of elimination - E2 mechanism - Zaitsev's rule - E1 mechanism - SN1 and E1 reactions - When is a mechanism E1 or E2? - E2 reactions in the synthesis of alkynes - When will a mechanism be SN1, SN2, E1 or E2?

9) Alcohols, ethers and epoxides.

Structures and bonding - Nomenclature - Physical properties - Preparations of alcohols, ethers and epoxides - Reactions of alcohols, ethers and epoxides - Dehydration of alcohols to alkenes - Conversion of alcohols to alkyl halides with HX - Conversion of alcohols to alkyl halides with SOCl2 and PBr3 - Alkyl Tosylate - Reactions of ethers with strong acids - Reactions of epoxides

10) Alkenes

Nomenclature - Physical properties - Preparation of alkenes - Introduction to addition reactions - Hydrohalogenation - Electrophilic addition of HX - Markovnikov's rule - Stereochemistry of electrophilic addition of HX - Hydration - Electrophilic addition of water - Halogenation - Halogen addition - Stereochemistry of halogenation - Formation of halide - Hydroboration-oxidation

11) Alkynes

Nomenclature - Physical properties - Preparation of alkynes - Reactions of alkynes - Addition of halogen acids - Addition of halogen - Addition of water - Hydroboration-oxidation - Reactions of acetylide anions12) Oxidation and reduction

12) Oxidation and reduction

Reducing agents - Reduction of alkenes - Reduction of alkynes - Oxidizing agents - Epoxidation - Dihydroxylation - Oxidative cleavage of alkenes - Oxidative cleavage of alkynes - Oxidation of alcohols - Biological oxidations

13) Radical Reactions.

General characteristics of radical reactions - Halogenation of alkanes - Mechanism of halogenation - Differences between chlorination and bromination - Radical halogenation to allyl carbon - Radical addition to double bonds - Radical polymerization - Antioxidants

14) Conjugation, resonance and dienes.

Conjugation - Resonance and allyl carbocation - Common examples of resonance - Resonance hybrids - Electron delocalization, hybridization and geometry - Conjugated dienes - Carbon-carbon bond length in 1,3-butadiene - Electrophilic addition: addition 1,2 and 1,4 - Kinetic and thermodynamically controlled products - Diels-Alder reaction

15) Benzene and aromatic compounds

Structure of benzene - Nomenclature of benzene derivatives - Criteria for aromaticity - Hückel's rule - Examples of aromatic compounds (monocyclic, polycyclic and heterocyclic aromatics)

16) Aromatic electrophilic substitution

Aromatic electrophilic substitution-General mechanism-Halogenation-Nitration and sulfonation-Friedel-Crafts alkylation and acylation-Substituted benzenes-Aromatic electrophilic substitution of substituted benzenes-Why substituents activate or deactivate the benzene ring-Orientation effects in substituted benzenes-Disubstituted benzenes-Synthesis of benzene derivatives-Oxidation and reduction of substituted benzenes-Multistage synthesis-Aromatic nucleophilic substitutions

17) Carbonyl compounds: aldehydes and ketones.

Structures and bonds - Nomenclature - Preparation of aldehydes and ketones - Reactions of aldehydes and ketones - Oxidation of aldehydes - Reduction of aldehydes and ketones - Nucleophilic addition of R- - Reaction of organometallic reagents as nucleophiles with aldehydes and ketones - Nucleophilic addition of -CN - Addition of primary and secondary amines - Addition of H2O - Addition of alcohols (Formation of acetals) - An introduction to carbohydrates - Carbonyl compounds α, β-unsaturated

18) Carboxylic compounds: carboxylic acids and derivatives.

Structure and bonding of carboxylic acids - Nomenclature of carboxylic acids - Preparation of carboxylic acids - Reactions of carboxylic acids - Characteristics of carboxylic acids - Substituted benzoic acids - Sulfonic acids - Amino acids - Structure and bonding of derivatives of carboxylic acids - Nomenclature of derivatives of carboxylic acids - Reduction of carboxylic acids and their derivatives - Reaction of acyl nucleophilic substitution - Reactions of organometallic reagents with derivatives of carboxylic acids - Reactions of chlorides of acids - Reactions of anhydrides - Reactions of carboxylic acids - Reactions of esters - Reactions of amides - Biological acylation reactions - Nitriles

19) Carbonyl and carboxylic compounds: condensation reactions in alpha

Enols - Enolates - Carbonyl reactions in α - Carbon halogenation in α - Direct alkylation of enolates - Synthesis with malonic ester - Synthesis with acetoacetic ester - Aldolic reaction - Cross aldolic reactions - Claisen reaction - Michael reaction

20) Amines

Structure and bonds - Nomenclature - Preparation of amines - Reactions of amines - Amines reacting as bases - Relative basicity of amines and other compounds - Amines reacting as nucleophiles - Reaction of amines with nitrous acid - Substitution reactions of aryldiazonium salts

21) Lipids

Waxes - Triacylglycerols - Phospholipids - Fat-soluble vitamins - Eicosanoids - Terpenes - Steroids

22) Carbohydrates

Monosaccharides - D-aldoses family - D-ketoses family - Cyclic forms of monosaccharides (Harworth projections) - Carbohydrate reactions (Hemiacetal reaction -Hydroxyl group reactions - Carbonyl group reactions - Disaccharides - Polysaccharides

23) Amino acids and proteins

Amino acids - Peptides - Peptide synthesis - Protein structure

24) Nucleic acids

Pyrimidines and purines - Nucleosides - Nucleotides - Phosphodiesters, oligonucleotides and polynucleotides - Nucleic acids

It is necessary to have passed the General an Inorganic Chemistry exam.

• D1 - Knowledge and Ability to Understand.

The student should know the principles underlying chemical bonding, the rules of nomenclature of organic compounds, to be able to point out the relationships between formulas, spatial structures and molecular properties.

The studnt should be familiar with the basic concepts of acidity and basicity according to Lewis, of stereochemistry, know and distinguish one enaniomer from another and the differences with diastereoisomers; he/she should also have mastered Fisher's Formulas.

The student should be able to identify the various functional groups, distinguish between an aliphatic and an aroamtic compost, the interactions between functional groups, their preparation and reactivity.

The student will be expected to know the main biomolecules and relationships that bind the various functional groups that comprise them and reactivity.

These skills will be tested through a written test and oral questions.

•  D2 - Ability to apply knowledge and understanding.

The student should be able to correctly use the various methods to describe an organic compound, nomenclature, symbologies to express reaction mechanisms, resonance formulas and distinguish their energy weight. He/she will also apply the acquired knowledge to interpret at a basic level the acid/base properties of organic compounds.

The student will be able to carry out synthesis and recognition activities of organic compounds by applying basic knowledge of the acid/base properties of organic compounds.

• D3 - Autonomy of judgment.

The student should be able to critically evaluate the structure and properties of an organic compound, both in terms of molecular complexity, stereochemistry, acid/base properties, and reactionary capabilities.

The knowledge acquired in the study of different functional groups will find its full application in the student's ability to evaluate in its complexity biomolecular systems of interest to the aims of the Course of Study.

These skills will be tested both by written test and by application-oriented oral questions.

• D4 - Communication Skills.

The student should be able to describe structural and rheational concepts learned in the course by expressing himself clearly, in appropriate terms and with appropriate examples.

• D5 - Learning skills.

The student should be able to construct his or her own scientific growth critically and independently, making proper use of the study material provided by the lecturer, in the form of texts and slides, and in-depth material that he or she may procure. These skills, as far as possible, will be stimulated by the lecturer by proposing in-depth studies and providing exercises to solve, which will then be explained and discussed during the lectures.

The teaching material prepared by the lecturer in addition to recommended textbooks (such as for instance slides, lecture notes, exercises, bibliography) and communications from the lecturer specific to the course can be found inside the Moodle platform › blended.uniurb.it

Classroom exercises

Teaching

The course involves face-to-face lectures in which the lecturer explains the concepts and offers practical exercises to promote understanding.

Students may intervene in the lectures to request clarifications from the lecturer.

Innovative teaching methods

The in-person teaching mode will be enriched with exercises and insights, both individual and group.

Some course topics will be covered following the practice of "Problem-based learning. For problem-based learning in small groups.

Attendance

Class attendance is not mandatory, but strongly recommended.

Elementary knowledge of general chemistry is required.

Course books

J. Gorzynski Smith, "Fondamenti di Chimica Organica", Quarta Edizione, McGraw-Hill Education, 2023.

Assessment

The assessment of learning involves a written test and an oral test.

The written test consists of solving six exercises ranging from the nomenclature of organic compounds to the chemistry of biomolecules. The exercises will be written according to types similar to the exercises carried out in the classroom by the lecturer. The evaluation of the written test is given in thirtieths and will be considered passed with a minimum grade of 18/30. The duration of the written test is 1.5 hours.

The oral test is reserved for students who have passed the written test and achieved a grade higher than 18/30 and will focus on questions covered in the course syllabus.

Disabilità e DSA

Le studentesse e gli studenti che hanno registrato la certificazione di disabilità o la certificazione di DSA presso l'Ufficio Inclusione e diritto allo studio, possono chiedere di utilizzare le mappe concettuali (per parole chiave) durante la prova di esame.

A tal fine, è necessario inviare le mappe, due settimane prima dell’appello di esame, alla o al docente del corso, che ne verificherà la coerenza con le indicazioni delle linee guida di ateneo e potrà chiederne la modifica.

Teaching

Teaching materials and specific teacher communications can be found, along with other supporting activities, within the Moodle platform ' blended.uniurb.it

Attendance

Class attendance is not mandatory, but strongly recommended.

Elementary knowledge of general chemistry is required.

Course books

J. Gorzynski Smith, "Fondamenti di Chimica Organica", Quarta Edizione, McGraw-Hill Education, 2023.

Assessment

The assessment of learning involves a written test and an oral test.

The written test consists of solving eight exercises ranging from the nomenclature of organic compounds to the chemistry of biomolecules. The exercises will be written according to types similar to the exercises carried out in the classroom by the lecturer. The evaluation of the written test is given in thirtieths and will be considered passed with a minimum grade of 18/30. The duration of the written test is 2 hours.

The oral test is reserved for students who have passed the written test and achieved a grade higher than 18/30 and will focus on questions covered in the course syllabus.

Disabilità e DSA

Le studentesse e gli studenti che hanno registrato la certificazione di disabilità o la certificazione di DSA presso l'Ufficio Inclusione e diritto allo studio, possono chiedere di utilizzare le mappe concettuali (per parole chiave) durante la prova di esame.

A tal fine, è necessario inviare le mappe, due settimane prima dell’appello di esame, alla o al docente del corso, che ne verificherà la coerenza con le indicazioni delle linee guida di ateneo e potrà chiederne la modifica.