OVERVIEW

The role of organic chemistry in the field of Materials Science has become increasingly prominent, driven by the design and synthesis of innovative organic materials with diverse properties and functions. As such, a foundational understanding of organic chemistry is essential for future materials scientists.

The teaching unit is structured to emphasize conceptual understanding and critical thinking, rather than the mere memorization of facts.

AIMS AND CONTENT

LEARNING OUTCOMES

Acquire basic knowledge regarding the nomenclature, structure and reactivity of the main organic compounds; acquire practical skills regarding simple experimental procedures.

AIMS AND LEARNING OUTCOMES

At the end of the teaching unit, the student will have acquired:

1 – Knowledge and understanding

The student will know and understand the fundamentals of organic chemistry, including molecular structure, major functional groups, nomenclature, reactivity of organic compounds, and associated reaction mechanisms. The student will also be familiar with some practical aspects of the subject.

2 – Applying knowledge and understanding

The student will be able to apply both theoretical and practical knowledge to:

(i) deduce the structure of an organic molecule from its name and vice versa,

(ii) predict the chemical behavior of organic compounds based on their structure,

(iii) interpret experimental results obtained during laboratory activities.

3 – Making judgements

The student will be able to identify appropriate conditions to carry out specific structural modifications on organic compounds. They will also be able to analyze chemical structures in order to select the most suitable purification technique.

4 – Communication skills

The student will be able to clearly and accurately communicate acquired knowledge using appropriate scientific language, and to present experimental data in a clear and organized manner. Interpersonal communication will be encouraged, particularly during classroom and/or laboratory exercises.

5 – Learning skills

The student will have developed the ability to independently use the foundational knowledge acquired to continue exploring and deepening their understanding of the subject.

PREREQUISITES

A solid understanding of General and Inorganic Chemistry is a necessary prerequisite and should be ensured by the student prior to undertaking this teaching unit.

TEACHING METHODS

The teaching unit is delivered through both classroom lectures and laboratory sessions. During lectures, individual and/or group exercises will be conducted, including the use of interactive tools such as Wooclap.

Class attendance is not mandatory, but it is strongly recommended.

Laboratory sessions (20 hours – 5 experiments), on the other hand, are compulsory. Students will be required to complete mandatory preparatory quizzes before each laboratory session. A written lab report must be submitted via Aulaweb within two weeks after the final lab session. The report will be reviewed and graded by the instructor. Since experiments will be carried out in pairs, only one report per pair is required; however, students are encouraged to collaborate fully in writing it.

Supplementary exercises to support preparation for the oral exam will be made available on Aulaweb. These exercises are also useful for student self-assessment.

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Students with valid certifications for Specific Learning Disabilities (SLD), disabilities, or other educational needs must contact the teacher and the inclusion representative of the School of Mathematical, Physical, and Natural Sciences (sergio.didomizio@unige.it) by email at the beginning of the lessons to agree on teaching methods that respect the objectives of the teaching unit while taking individual learning needs into account.

For more information:
https://unige.it/disabilita-dsa/richiesta-servizi

SYLLABUS/CONTENT

PART 1: Introduction to Organic Chemistry

• Introduction: What is Organic Chemistry?

• Chemical Bonding in Organic Compounds

• Lewis Structures and the Octet Rule

• Formal Charge

• Molecular Orbital Theory

• Inductive Effect

• Representation of Organic Compounds and Resonance

• Lewis Structures, Condensed Structural Formulas, and Skeletal (Line-Angle) Formulas

• Resonance

PART 2: Hydrocarbons, Functional Groups, Nomenclature, and Structural Isomerism

• Hydrocarbons

• Alkanes, Alkenes, Alkynes, and Their Nomenclature

• Aromatic Compounds and Nomenclature

• Constitutional Isomerism

• Functional Groups and Nomenclature

PART 3: Physical Properties of Organic Compounds

• Intermolecular Forces

• Boiling and Melting Points

• Solubility

• Density

PART 4: Acid–Base Properties

• Brønsted–Lowry Acids and Bases

• Position of Acid–Base Equilibria

• pKa: Definition and Values for the Main Organic Compounds

• Factors Affecting Acidity

• Substituent Effects

• pH and pKa: The Henderson–Hasselbalch Equation

PART 5: Conformations of Organic Compounds

• Conformers

• Torsional, Steric, and Angle Strain

• Thermodynamic and Kinetic Aspects

• Newman Projections

• Conformations of Acyclic Alkanes

• Conformations of Cycloalkanes

PART 6: Stereoisomerism

• Stereoisomers: Enantiomers and Diastereomers

• Chirality and Stereogenic Centers

• Perspective Formulas and Fischer Projections

• R/S Configuration Notation

• Molecules with Multiple Stereocenters: Enantiomers, Diastereomers, and Meso Compounds

• Stereoisomerism in Alkenes

• Optical Activity: Polarimetry and Specific Rotation

• Mixtures of Enantiomers

• Chemical Properties of Enantiomers

PART 7: Organic Reactions

• Thermodynamic and Kinetic Control

• Classification of Organic Reactions

• Nucleophiles and Electrophiles

PART 8: Reactions of Carbon–Carbon Double Bonds (C=C)

• Electrophilic Addition: Mechanism and Markovnikov's Rule

• Addition of Hydrogen Halides, Water, and Halogens

• Catalytic Hydrogenation

• Stereochemical Aspects

PART 9: Aromatic Compounds and Electrophilic Aromatic Substitution

• Benzene and Aromaticity

• Heteroaromatic Compounds and Their Basic Properties

• The Five Electrophilic Aromatic Substitution Reactions and Their Mechanisms

• Activating/Deactivating and Ortho/Para-Directing Effects of Substituents

PART 10: Reactions of the Carbonyl Group (C=O) in Aldehydes and Ketones

• Nucleophilic Addition and Its Mechanism

• Oxygen Nucleophiles (Water and Alcohols), Nitrogen Nucleophiles (Primary Amines), and Carbon Nucleophiles (HCN and Organometallic Reagents)

• Conjugate Nucleophilic Addition

• Keto–Enol Tautomerism

PART 11: Reactions of the Carbonyl Group (C=O) in Carboxylic Acids and Their Derivatives

• Nucleophilic Acyl Substitution: Thermodynamic and Kinetic Aspects

• Reactivity of Carboxylic Acid Derivatives

• Reactions with Oxygen Nucleophiles (Water, Alcohols) and Nitrogen Nucleophiles (Ammonia and Amines)

• Preparation of the More Reactive Carboxylic Acid Derivatives

• Reactions with Carbon Nucleophiles

• Nitriles

PART 12: Reactions at the α-Carbon of Carbonyl Compounds

• Enolate Anions

• Aldol Addition and Aldol Condensation

• Claisen Condensation

PART 13: Nucleophilic Substitution at Saturated Carbon and Elimination Reactions

• General Principles

• Bimolecular Nucleophilic Substitution (SN2): Mechanism and Stereospecificity

• Effects of the Leaving Group, Nucleophile Strength, Steric Hindrance, and Solvent

• E2 Elimination: Mechanism and Competition between SN2 and E2

• Synthetic Applications of SN2: Synthesis of Alcohols, Williamson Ether Synthesis, and Synthesis of Amines

• Unimolecular Nucleophilic Substitution (SN1): Mechanism, Factors Favoring SN1, and Comparison of SN1 vs SN2

• E1 Elimination

PART 14: Oxidation and Reduction Reactions

• Determination of the Oxidation State of Carbon

• Oxidation and Reduction at Carbon

• Complex Hydrides and Their Use in the Reduction of Carbonyl Compounds and Esters

• Reductive Amination

• Oxidation of Alcohols and Aldehydes

• Oxidation of Carbon–Carbon Double Bonds: Epoxidation and Osmylation

• Introduction to Oxidation–Reduction Reactions of Nitrogen and Sulfur

PART 15: Carbohydrates

• Structure and Stereochemistry of the Major Monosaccharides

• Hemiacetal Forms of Monosaccharides

• Mutarotation

• Glycosides

• Disaccharides: Sucrose, Lactose, and Maltose

• Polysaccharides: Starch, Glycogen, and Cellulose

PART 16: Proteins

• Classification of the Proteinogenic Amino Acids

• Stereochemistry of Amino Acids

• Acid–Base Properties of Amino Acids

• Isoelectric Point and Electrophoresis

• The Peptide Bond

• Protein Structure

PART 17: Nucleic Acids

• Nitrogenous Bases

• Nucleosides and Nucleotides

• The DNA Double Helix

• Introduction to Replication, Transcription, and Translation

• DNA vs RNA

PART 18: Lipids

• Fatty Acids

• Waxes, Triglycerides, and Phospholipids

• Introduction to Terpenes, Steroids, and Fat-Soluble Vitamins

PART 19: Radicals (Overview)

• Radical Reactions and Radical Halogenation of Alkanes

• Oxygen as a Radical Reagent and Radical Inhibitors

• Radicals and Ozone

PART 20: Polymers (Overview)

• Radical Polymerization

• Polyesters, Polyamides, Polycarbonates, and Polyurethanes

• Bio-based Polymers

LABORATORY: Theory

• Crystallization

• Melting Point Determination

• Distillation

• Chromatography

• Liquid–Liquid Extraction

• Introduction to Laboratory Experiments

LABORATORY EXPERIMENTS

1.Distillation and Crystallization

2.Liquid–Liquid Extraction

3.Chromatography

4.Synthesis of Acetylsalicylic Acid

5.Classical Resolution of α-Methylbenzylamine and Polarimetry

RECOMMENDED READING/BIBLIOGRAPHY

Teaching materials are available on Aulaweb.

Students are advised to complement the provided materials with their own lecture notes; for this reason, attending classes is strongly recommended.

Consulting an Organic Chemistry textbook for non-chemistry majors may also be helpful (copies are available in the library). Some recommended titles include:

· W. H. Brown "Introduzione alla Chimica Organica", EdiSES

· J. McMurry "Fondamenti di Chimica Organica", Zanichelli

· J.G. Smith "Fondamenti di Chimica Organica", McGraw Hill

· L.G. Wade "Fondamenti di Chimica Organica", Piccin

· D. Klein, "Fondamenti di Chimica Organica", Pearson

· P. Y. Bruice, «Elementi di Chimica Organica», EdiSES

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

Lectures will begin as indicated in the academic calendar. Updates will also be posted on Aulaweb. Class Schedule: The timetable for this teaching unit is available via the Portale EasyAcademy, or the MyUniGe app

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

The exam consists of an oral assessment covering the entire teaching unit program, aimed at evaluating the achievement of the learning objectives.

During the oral exam, students will be required to demonstrate their ability to write chemical formulas and equations, and to correctly describe the reactivity and properties of the various classes of molecules studied, as well as the laboratory techniques covered during the teaching unit.

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Students with valid certifications for Specific Learning Disabilities (SLD), disabilities, or other educational needs may request exam adaptations by completing the dedicated online form at least seven days before the exam:

https://modulionline.unige.it/richiesta-adattamenti#no-back

They should also contact the teacher and the inclusion representative of the School of Mathematical, Physical, and Natural Sciences (sergio.didomizio@unige.it) by email.

For more information:
https://unige.it/disabilita-dsa/richiesta-servizi

ASSESSMENT METHODS

The assessment methods will prioritize the student's logical reasoning and problem-solving abilities over mere rote memorization. During the oral exam, the instructor will aim to guide the student toward a correct explanation, even in cases where the topic is not recalled in full, by encouraging reasoning based on fundamental principles and logic.

The oral exam will be used to assess whether the student has achieved the intended learning outcomes.

Students are advised, during their preparation, to practice writing chemical formulas and stoichiometric equations, as what is written on the board during the exam will carry equal weight to the oral explanation.

FURTHER INFORMATION

Classroom attendance is not mandatory, but it is strongly recommended.

In general, please refer to Aulaweb for all details and/or updates.