Organic Chemistry A - L
Academic Year 2026/2027 - Teacher: VENERANDO PISTARA'Expected Learning Outcomes
Knowledge and Understanding
Upon completion of the course, students will be able to describe and explain the fundamental principles of Organic Chemistry, the structure and properties of the main classes of organic compounds, the rules of nomenclature and stereochemistry, and the main mechanisms of organic reactions.
Ability to Apply Knowledge and Understanding
Students will be able to apply their acquired knowledge to represent and name the main classes of organic compounds, predict the reactivity and products of the main organic reactions, and propose simple reaction mechanisms. They will also be able to correlate molecular structure with the chemical-physical properties and reactivity of organic compounds.
Making Independent Judgments
Students will be able to analyze and evaluate the reactivity of organic compounds based on their molecular and electronic structures, compare different reaction pathways, and justify their choices in solving simple Organic Chemistry problems.
Communication Skills
Students will be able to describe and illustrate the structures, properties, and transformations of organic compounds and to explain the mechanisms and chemical transformations using appropriate scientific terminology.
Learning Skills
Students will be able to independently use reference texts and course materials to delve deeper into organic chemistry topics and integrate their acquired knowledge into solving new problems.
Course Structure
The teaching is given as lectures (8 CFU) and exercises (2 CFU)
Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes in line with the planned programme.
For better learning of the course content, it is recommended that students actively participate in the topics covered during lectures and classroom exercises.
In the case of students with disabilities and/or SLD, in accordance with the Italian Law (170/2010), it is possible to adapt assessment and study methods, without modifying learning objectives; this support includes dispensatory measures and compensatory tools. To request the service, the student must inform the professor at the beginning of the course or at least 30 days before the exam.
Furthermore, it is possible to contact Prof. Teresa Musumenci, CInAP (Centro per l’Integrazione Attiva e Partecipata - Servizi per le Disabilità e/o DSA) referent teacher of our Department.
Required Prerequisites
The students must know the fundamentals of General and Inorganic Chemistry and in particular:
Periodic table – Atomic structure and electronic configuration – Ionic and covalent bonds – Atomic and molecular orbitals – Valence bond theory – Structural formulas – Hybrid carbon, oxygen and nitrogen orbitals – Acids and bases, definitions of pKa and pH and equilibrium – Acidity and basicity according to Brønsted-Lowry and Lewis – Thermodynamics and kinetics – Values of ΔH - Catalysis.
The aforementioned topics can be found in the first chapters of any Organic Chemistry textbook.
Attendance of Lessons
Detailed Course Content
PART 1: An Introduction to the Study of Organic Chemistry
1. Remembering General Chemistry: Electronic Structure and Bonding
2. Acids and Bases: Central to Understanding Organic Chemistry
3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure
PART 2: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization
4. Isomers: The Arrangement of Atoms in Space
5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity
6. The Reactions of Alkenes – The Stereochemistry of Addition Reactions
7. The Reactions of Alkynes – An Introduction to Multistep Synthesis
8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction – Aromaticity and Electronic Effects: An Introduction the Reactions of Benzene
PART 3: Substitution and Elimination Reactions
9. Substitution and Elimination Reactions of Alkyl Halides
10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
11. Organometallic Compounds
12. Radicals
PART 4: Carbonyl Compounds
15. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
16. Reactions of Aldehydes and Ketones – More Reactions of Carboxylic Acid Derivatives
17. Reactions at the α-Carbon
PART 5: Aromatic Compounds
18. Reactions of Benzene And Substituted Benzenes
19. Reactions of Amines
19/1. The Chemistry of Heteroaromatic Compounds
PART 6: Bioorganic Compounds
20. The Organic Chemistry of Carbohydrates
21. The Organic Chemistry of Amino Acids, Peptides, and Proteins
25. The Organic Chemistry of Lipids
26. The Organic Chemistry of Nucleic Acids
Textbook Information
| Author | Title | Publisher | Year | ISBN |
|---|---|---|---|---|
| 1) P. Y. Bruice | Chimica Organica | EdiSES | III ed. 2017 | 9788879599351 |
| 2) L. G. Wade | Fondamenti di Chimica Organica | Piccin | VIII ed. 2014 | 9788829923007 |
| 3) J. Gorzynski Smith | Fondamenti di Chimica Organica | McGraw Hill | IV ed. 2023 | 9788838656576 |
| 4) N. E. Schore e P. C. Vollhardt | Esercizi risolti di Chimica Organica | Zanichelli | IV ed. 2016 | 9788808436900 |
Course Planning
| Subjects | Text References | |
|---|---|---|
| 1 | Remembering General Chemistry: Electronic Structure and Bonding | 1) Bruice, cap. 1 |
| 2 | Acids and Bases: Central to Understanding Organic Chemistry | 1) Bruice, cap. 2 |
| 3 | An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure | 1) Bruice, cap. 3 |
| 4 | Isomers: The Arrangement of Atoms in Space | 1) Bruice, cap. 4 |
| 5 | Alkenes: Structure, Nomenclature, and an Introduction to Reactivity - Thermodynamics and Kinetics | 1) Bruice, cap. 5 |
| 6 | The Reactions of Alkenes - The Stereochemistry of Addition Reactions | 1) Bruice, cap. 6; 2) Wade, paras. 8.5, 11.5 |
| 7 | The Reactions of Alkynes - An Introduction to Multistep Synthesis | 1) Bruice, cap. 7 |
| 8 | Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction - Aromaticity and Electronic Effects: An Introduction the Reactions of Benzene | 1) Bruice, cap. 8 |
| 9 | Substitution and Elimination Reactions of Alkyl Halides | 1) Bruice, cap. 9 |
| 10 | Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds | 1) Bruice, cap. 10 |
| 11 | Organometallic Compounds | 1) Bruice, cap. 11 |
| 12 | Radicals | 1) Bruice, cap. 12 |
| 13 | Reactions of Carboxylic Acids and Carboxylic Acid Derivatives | 1) Bruice, cap. 15 |
| 14 | Reactions of Aldehydes and Ketones - More Reactions of Carboxylic Acid Derivatives | 1) Bruice, cap. 16 |
| 15 | Reactions at the α-Carbon | 1) Bruice, cap. 17 |
| 16 | Reactions of Benzene And Substituted Benzenes | 1) Bruice, cap. 18 |
| 17 | Amines | 2) Wade, cap. 16 |
| 18 | La Chimica degli Eterocicli Aromatici | 2) Wade, paras. 13.8, 13.16, 16.8 |
| 19 | The Organic Chemistry Of Carbohydrates | 1) Bruice, cap. 20 |
| 20 | The Organic Chemistry Of Amino Acids, Peptides, and Proteins | 1) Bruice, cap. 21 |
| 21 | Catalysis in Organic Reactions and in Enzymatic Reactions | 1) Bruice, cap. 22 |
| 22 | The Organic Chemistry of Lipids | 1) Bruice, cap. 25 |
| 23 | The Organic Chemistry of the Nucleic Acids | 1) Bruice, cap. 26 |
Learning Assessment
Learning Assessment Procedures
The level of acquisition of the educational objectives will be verified through a final exam consisting of a written test followed by an oral interview. Passing the written test with 18/30 is an essential condition for accessing the oral interview.
Booking for the exam is mandatory; it is active up to four days before the date reported in the exam calendar.
The written test (90 minutes) consists of 30 multiple choice questions (5 answers, only one exact – 1 pt. for correct, -0.25 for wrong and 0 for not given answer). It is to be held without the help of notes or a book and includes the entire program.
The written test will be passed with a minimum of 18/30.
The oral exam consists of a discussion (about 30 minutes), aimed at ascertaining the level of knowledge and understanding reached by the student regarding the theoretical and methodological contents indicated in the program; it will take place at least two days after the written test and the date will be communicated on the Department website, "news" section.
The final evaluation will be established based on the scores achieved in both tests. The oral exam is not aimed at raising the grade obtained in the written test but, with a negative result, it may result in rejection and the written test must be repeated.
As a result of special conditions, the verification of learning can also be carried out remotely.
For logistical reasons, the number of questions and the time required for their execution can be modified.
Examples of frequently asked questions and / or exercises
Sort the following compounds in order of increasing acidity.
Indicate among the following species the strongest nucleophile in a polar protic solvent.
Propose a mechanism for the following transformation.
Write the product and mechanism of the following reaction.
Complete the following reactions.
Describe the elongation of the chain of a monosaccharide.