OVERVIEW

Studying organic chemistry offers an opportunity to explore an exciting and vital science. The foundations of this discipline lay the foundation for subsequent studies in medical, biological, chemical, and materials sciences. Furthermore, applying this knowledge allows students to understand some modern technologies in everyday use. Through the recognition of functional groups, the three-dimensional design of molecular structures, and the interpretation of mechanistic reaction processes, students will gain theoretical training that will be useful for successfully undertaking and successfully completing subsequent theoretical and practical courses, such as pharmaceutical chemistry, biochemistry, drug analysis, organic chemistry laboratory work, and so on. This training also aims to provide students with the basic elements of organic chemistry necessary to develop professional skills for the careers that future graduates in Chemistry and Pharmaceutical Technologies (CTF) envision.

AIMS AND CONTENT

LEARNING OUTCOMES

The course aims to provide and make students learn the logical and systematic tools necessary to achieve a basic knowledge of the structure, physical characteristics, reactivity, mechanistic action and preparation of the main functional groups of organic chemistry, as a platform to address the subsequent Organic II course.

AIMS AND LEARNING OUTCOMES

Students will be guided to study organic chemistry to acquire a set of skills and abilities useful for completing a scientific education. This will enable them to analyze, classify, explain, and predict the basic reactivity of major organic compounds, highlighting molecules that are part of everyday life, their benefits, and their risks to the health of living beings and the environment, in order to emphasize the practical, not just academic, utility of the subject. Students will be expected to understand the fundamental theories in order to solve general organic chemistry problems through reasoning. They will be expected to be able to argue theories, master graphic design skills, and use correct, technical language to demonstrate measurable learning outcomes during written and oral exams.

At the end of the course, students will be able to:

Use the periodic table to determine the ground-state electronic configuration and bonding geometries of a central atom;
Interpret atomistic and molecular theories to understand the strength and nature of chemical bonds;
Predict the chemical nature (electrophile, nucleophile, acid, and base) of an atom within a molecular structure;
Master the fundamental concepts of stereochemistry and draw chiral molecules on paper;
Visualize and orient substituents in a molecule in space, as well as represent structural changes during a multistep reaction;
Classify the reactivity of organic compounds and functional groups within a molecule or between different molecules;
Recognize the acidic or basic nature and strength of a given compound by assigning the position of an acid-base equilibrium;
Recognize the electrophilicity, nucleophilicity, and exit propensity of a given atom or functional group;
Determine the relative stability of carbocations and radicals to understand the progress of a reaction for a specific mechanism;
Predict whether a reaction will occur or not, and by what mechanism;
Correctly draw curved arrows to represent the flow of electrons in an ionic reaction and in radical processes;
Represent the resonance limit structures of a compound;
Understand the connections between the organic reactions studied and those occurring in nature and in cell biology.

PREREQUISITES

Having passed the general and inorganic chemistry exam, the study of which should not be limited only to passing this preliminary exam but should provide the concrete basis for dealing with the Organic Chemistry 1 course. The mere, unreasoned study of General and Inorganic Chemistry for the sole purpose of the grade, while qualifying the student for the Organic 1 exam, will create many difficulties for the student in dealing with both the course and the learning of the concepts of Organic Chemistry 1 and the related exam.

TEACHING METHODS

The course consists of 3 weekly lectures of two hours each, covering the entire syllabus.

Lesson support materials (presentations, exercises, and in-depth articles) are provided to students via the Aulaweb platform and/or Teams. Essential texts are recommended for studying the theory and completing the exercises. Part of the lesson is compiled in real time on the board or via tablet during the lessons, creating the final version of the slides that will be uploaded to Aula Web for the relevant year. Chemical reactions and their mechanisms are also performed using the same methods. To ensure a dynamic approach to the lessons, students are required to actively participate in answering questions and completing exercises individually or in groups. Quizzes and exercises will be available on the Aulaweb platform and/or Teams to keep students updated, allowing for effective support throughout the organic chemistry course, without being used for assessment purposes by the instructor.

Study tips:

1) Keep your weekly study material up to date, never let it pile up;

2) Study the material in small units and ensure you understand each new section before moving on to the next;

3) Solve all problems in each chapter before moving on to the next;

4) Write down theory and exercises in a notebook while studying;

5) Learn by teaching and explaining (studying better in groups);

6) Use molecular models while studying.

Students with valid certifications for Specific Learning Disabilities (SLD), disabilities, or other educational needs, regularly submitted to the University, are invited to contact the instructor and the School/Department Disability Coordinator (Prof. Luca Raiteri, Luca.Raiteri@unige.it) at the beginning of the course to discuss possible teaching methods that, while respecting the course objectives, take into account individual learning styles. IMPORTANT: Requests for adaptations during the exam MUST be made at least 10 working days before the scheduled exam date, carefully following the instructions in the link on the page https://unige.it/disabilita-dsa/comunicazioni.

SYLLABUS/CONTENT

1. Fundamentals of General Chemistry: Electronic Structure and Bonding

Atomic structure and electron distribution within an atom. Covalent bonds (polar and nonpolar). Representations of the structure of a compound. Atomic and molecular orbitals. Valence bond theory, VSEPR model, and molecular orbital theory (MOT). Hybridization of carbon and the formation of single, double, and triple bonds. Hybridization of other atoms (B, O, N) and their molecular geometries. Dipole moment of a bond and dipole moment of a molecule.

2. Acids and Bases: Fundamental Concepts in Organic Chemistry

Organic acids and bases. Definition of Ka and pKa. Predicting the position of an acid-base equilibrium via pKa. Factors that influence the strength of an acid and its pKa. Arrhenius, Bronsted-Lowry, and Lewis acid-base theories. Using curved arrows to represent the flow of electrons involved in an acid-base reaction.

3. Introduction to organic compounds: nomenclature, physical properties, and structure

Nomenclature of alkanes and cycloalkanes, alcohols and ethers, alkyl halides, and amines. Rotation around the single sigma bond (C-C). Conformational analysis of alkanes and their rotamers. Newman projection of the conformational isomers of a linear alkane. Ring strain of cycloalkanes. Conformational analysis of cyclohexane. Conformers of mono-, di-, and trisubstituted cyclohexanes. Cis-trans isomerism of cycloalkanes.

4. Isomers: the arrangement of atoms in space

Constitutional isomers and stereoisomers. Geometric isomerism (cis-trans and E/Z) in compounds with double bonds. Concept of chirality. Chiral molecules with an asymmetric center (stereogenic center). Representation of enantiomers and R,S descriptors for chiral carbons. Fischer projection. Origin of the optical activity of chiral compounds. Optical rotatory power. Molecules with multiple chiral centers (diastereomers and meso compounds).

5. Alkenes: Structure, nomenclature, and introduction to reactivity

Reactivity of alkenes and use of curved arrows. Mechanism of a reaction between a nucleophile and an electrophile.

6. Reactions of alkenes

Addition of water and hydrohalic acids to alkenes. Stability of carbocations and radicals. Rearrangement of carbocations. Regioselectivity of electrophilic addition reactions (Markovnikov's rule) and radical addition reactions (anti-Markovnikov). Hydroboration-oxidation of alkenes. Addition of halogens to alkenes. Addition of a peroxyacid to alkenes (epoxidation). Addition of ozone to alkenes (ozonolysis). Addition of hydrogen to alkenes (catalytic hydrogenation). Stereochemistry of addition reactions to alkenes: regioselective, stereoselective, or stereospecific reactions.

7. Reactions of alkynes

Nomenclature, structure, and reactivity of alkynes. Electrophilic additions to alkynes: introduction to keto-enol tautomerism. Catalytic hydrogenation of alkenes and its stereochemistry. Acidity of alkynes. Use of acetylide ions in organic synthesis.

8. Electronic delocalization, resonance structures, and its effect on stability, pKa

The bonds of benzene, resonance limit structures, and resonance hybrids. Predicting the stability of resonance structures. Stability of dienes, allylic, and benzylic cations. Effect of electronic delocalization on pKa.

9. Substitution and Elimination Reactions of Alkyl Halides

Mechanism of a bimolecular (SN2) and monomolecular (SN1) nucleophilic substitution reaction. Factors influencing SN2 and SN1 reactions. Elimination reactions of alkyl halides (E2 and E1). Stereochemistry and competition between SN2, SN1, E2, and E1 reactions.

10. Reactions of Alcohols, Ethers, Epoxides, and Amines

Nucleophilic substitution reactions of alcohols. Elimination reactions (E1 and E2) of alcohols (dehydration). Stereochemistry of the dehydration reaction. Oxidation of alcohols. Nucleophilic substitution reactions of ethers and epoxides. Formation of cis and trans diols.

11. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Structure, physical properties, and reactivity of carboxylic acid derivatives (acyl chloride, anhydride, ester, and amide).

12. Reactions of Aldehydes and Ketones

Reactivity of Carbonyl Compounds. Addition of Strong and Weak Nucleophiles to the Carbonyl Carbon. Preparation of Organolithium and Organomagnesium Compounds and Their Addition to the Carbonyl Carbon. Formation of Imines and Enamines. Formation of Acetals and Hemiacetals as Carbonyl Protecting Groups. Wittig Reaction.

13. Reactions at the Alpha-Carbon

Acidity of the Alpha-Hydrogen of Carbonyl Derivatives. Keto-enol Tautomerism. Halogenation of the Alpha-Carbon of Aldehydes and Ketones. Kinetic and Thermodynamic Formation of the Enolate Ion. Base-Catalyzed Alkylation of the Alpha-Carbon. Stork reaction. Aldol self-condensation.

14. Reactions of Benzene and Substituted Benzenes

Aromaticity Criteria and Hueckel's Rule. Aromaticity according to molecular orbital theory (Frost's Rule). Nomenclature of monosubstituted benzenes. Electrophilic aromatic substitution (SEAr) reactions: halogenation, nitration, sulfonation, acylation, and Friedel-Crafts alkylation. Chemical transformations of substituents on the benzene ring. Effect of substituents on the reactivity of a benzene ring. Effect of substituents on the orientation of a SEAr.

RECOMMENDED READING/BIBLIOGRAPHY

Paula Yurkanis Bruice, Elements of Organic Chemistry, Ed. EdiSES
Other titles and publishers will be provided on the slides of the first introductory lecture.

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

September 28, 2026, barring unforeseen circumstances. In this case, the new date will be announced on AulaWEb 2026. Registration is free and independent.

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

Written exam with open-ended and/or multiple-choice questions.

This is followed by a correction phase for the written papers by the students themselves, working in pairs, followed by a thoughtful presentation of the solutions to the exercises by the teacher on the board. Self-assessment among students encourages reflection on their own and others' papers, encouraging responsible self-correction. After correction, students will be informed of their score and may request explanations.

Those who achieve a minimum score of 17 will proceed to the oral exam with a conditional or standard pass. Those admitted with a conditional pass will have to complete a short written exam during the oral exam aimed at reaching/exceeding the standard pass mark of 18.

ASSESSMENT METHODS

The written exam will include purely theoretical questions or organic chemistry exercises to be completed in three hours.

The assessment tools provided in the teaching and examination procedures, which accompany the teaching-learning process, are designed to assess the levels of knowledge, skills, and competences achieved by students.

FURTHER INFORMATION

Rivolgersi al docente per ulteriori informazioni non comprese nella scheda insegnamento.