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 (IUPAC and common names), physicochemical properties of organic compounds, and 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 provided. Attention will also be paid to the main classes of organic compounds of biological relevance: 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 - 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 (Ethane and butane) -- Conformation of cyclic alkanes (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 formation-Thermodynamics-Energy diagrams for single- and two-stage reaction mechanisms-Kinetics-Hammond's postulate-Catalysts

7) Alkyl halides and substitution reactions.

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

8) Alkyl halides and elimination reactions.

General characteristics of elimination - Alkenes: the products of elimination reactions - Mechanism of elimination (E2 and E1) - 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 - Markovnikov's rule - Hydration - Halogenation - Formation of halohydrins - Hydroboration-oxidation

11) Alkynes

Nomenclature - Physical properties - Preparation of alkynes - Reactions of alkynes - Hydrohalogenation - Hydration - Halogenation - Hydroboration-oxidation - Reactions of acetylide anions

12) Oxidation and reduction

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

13) Radical Reactions

General characteristics of radical reactions - Halogenation of alkanes - 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 - Hybrid resonance - Electron delocalization, hybridization and geometry - Conjugated dienes - 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 (activating or deactivating substituents)-Oxidations and reductions of substituted benzenes-Multistage synthesis-Aromatic nucleophilic substitutions

17) Carbonyl compounds: aldehydes and ketones

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

18) Carboxylic compounds: carboxylic acids and derivatives

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 with organometallic reagents - Reactions of acid chlorides - 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-Carbon reactions in α (halogenation and alkylation)-Malonic synthesis-Acetoacetic synthesis-Aldolic reaction-Cross aldolic reaction-Claisen reaction-Michael reaction

20) Amines

Structure and bonding - Nomenclature - Preparation of amines - Basicity of amines - Reactions of amines - 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) - Reaction of carbohydrates (Reaction of the hemiacetal, hydroxynyl and carbonyl groups) - Disaccharides - Polysaccharides

23) Amino acids and proteins

Amino acids - Peptides - Synthesis of peptides - Proteins (Primary, secondary, tertiary and quaternary structure)

24) Nucleic acids

Nitrogenous bases (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 understanding skills.

Upon completion of this training activity, students should demonstrate that they are able to:

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

2) to know the basic concepts of acidity and basicity according to Lewis, of stereochemistry,

3) know the basic concepts of stereochemistry.

4) know the various functional groups

5) know the preparation and reactivity of the various functional groups

6) know the main biomolecules and relationships that bind the various functional groups that comprise them.

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

    D2 - Ability to apply knowledge and understanding.

At the end of this training activity, students should demonstrate that they are able to:

1) correctly use the various methods to describe an organic compound, nomenclature, symbologies to express reaction mechanisms, resonance formulas and distinguish their energy weight.

2) interpret the acid/base properties of organic compounds.

3) describe the synthesis and reactivity of various organic compounds.

These skills will be assessed through a written test.

    D3 - Autonomy of judgment.

Upon completion of this training activity, students will be expected to demonstrate the ability to:

1) critically analyze the structure and properties of organic compounds, with emphasis on molecular complexity, stereochemistry, acid-base characteristics and reactivity.

2) use the knowledge gained about functional groups to biological systems.

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

    D4 - Communication Skills. 

Upon completion of the course, students should be able to clearly describe the structural and reactive concepts learned in the course, using appropriate terminology and supporting the exposition with relevant examples.

    D5 - Learning skills. 

At the end of the course, students should be able to build his or her 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

During the course, self-assessment tests will be offered through multiple-choice quizzes uploaded on the Moodle platform ' blended.uniurb.it

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

Problem-based learning.

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, each of which awards a maximum score of 4 points, for an overall total of 32 points. However, the final score will be converted into thirtieths, in accordance with the standard academic grading scale.

The exercises proposed in the written test will belong to the following types:

   1. Exercises on nomenclature of organic compounds.

   2. Exercises concerning stereochemistry.

   3. Classification and comparison in ascending or descending order of acidity, basicity or reactivity.

   4. Given the structure of the starting material and product, identification of the reagents needed for transformation.

   5. Given the structure of the starting material and reactants, prediction of the reaction product.

   6. Description of the mechanism of a specific reaction.

   7. Four multiple-choice questions related to the biomolecules section of the course.

    8. Given the structure of a drug, identification of functional groups, stereogenic centers, acid and base groups, and hydrogen bond donor and acceptor groups.

Exercises will be written according to types similar to the exercises carried out in the classroom. 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.

Disability and Specific Learning Disorders (SLD)

Students who have registered their disability certification or SLD certification with the Inclusion and Right to Study Office can request to use conceptual maps (for keywords) during exams.

To this end, it is necessary to send the maps, two weeks before the exam date, to the course instructor, who will verify their compliance with the university guidelines and may request modifications.

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, each of which awards a maximum score of 4 points, for an overall total of 32 points. However, the final score will be converted into thirtieths, in accordance with the standard academic grading scale.

The exercises proposed in the written test will belong to the following types:

   1. Exercises on nomenclature of organic compounds.

   2. Exercises concerning stereochemistry.

   3. Classification and comparison in ascending or descending order of acidity, basicity or reactivity.

   4. Given the structure of the starting material and product, identification of the reagents needed for transformation.

   5. Given the structure of the starting material and reactants, prediction of the reaction product.

   6. Description of the mechanism of a specific reaction.

   7. Four multiple-choice questions related to the biomolecules section of the course.

    8. Given the structure of a drug, identification of functional groups, stereogenic centers, acid and base groups, and hydrogen bond donor and acceptor groups.

Exercises will be written according to types similar to the exercises carried out in the classroom. 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.

Disability and Specific Learning Disorders (SLD)

Students who have registered their disability certification or SLD certification with the Inclusion and Right to Study Office can request to use conceptual maps (for keywords) during exams.

To this end, it is necessary to send the maps, two weeks before the exam date, to the course instructor, who will verify their compliance with the university guidelines and may request modifications.