Ateneo - UPO

The module provides the basic knowledge of organic chemistry: the concepts and language necessary for the study of organic chemistry as well as key elements on nomenclature, structure and reactivity of the most common classes of organic compounds. See “Programma esteso” (Extended Program) for more detailed information.

J. Clayden, N. Greeves, S. Warren, "Organic Chemistry" PICCIN.
P. Yurkanis Bruice, Organic Chemistry; EdiSES
Brown, Foote, Iverson, Organic Chemistry; EdiSES.
For this course, it is advisable to use one of the following exercise books:
M.V. D'Auria, O. Taglialatela Scafati, A. Zampella, "Esercizi di Chimica Organica", Loghìa, Napoli, 2007.
T.W. G. Solomons, C. B. Fryhle, R. G. Johnson, “La Chimica Organica attraverso gli esercizi”, Zanichelli, Bologna, 2010.

Knowledge and understanding.
The course aims to provide the basics of the chemistry of carbon compounds through the knowledge of the structure and reactivity of the main functional groups, the mechanisms of the most important reactions and the fundamental principles of organic stereochemistry.
Ability to apply knowledge and understanding.
The student will be able to apply the theoretical concepts assimilated to solve exercises of nomenclature, streochemistry and reactivity of organic molecules.
Communication skills.
The student must have acquired and will have to know how to use an appropriate chemical vocabulary in relation to the topics covered in the course. It should also be able to present correctly, clearly and concisely, the mechanisms by which organic molecules react and know how to predict the products of a reaction.
Making judgments
The student must be able to predict the properties and reactivity of a molecule on the basis of the structure of a compound and its similarity with the families of compounds studied.
The student must also demonstrate the ability to link/compare the different topics covered during the course.
Learning skills
The student must be able to use the teaching material (slides and exercises provided by the teacher, textbooks) for a detailed, critical and reasoned study.

Knowledge of the subjects taught in the General Chemistry course.

The course is based on classroom lectures, powerpoint presentations and guided exercises. The slides used during the lessons will be provided to the students through the D.I.R. platform.
In addition to the lectures, exercises will be held in the classroom by the teacher also with the involvement of students to learn more in detail about the topics covered in class. The concepts covered by the course will be discussed collegially in the classroom and applied directly in the exercises to stimulate students' critical sense and independence of judgment. Communication skills will be stimulated using appropriate terminology. The learning skills will be favored through the integration of textbooks with material provided by the teacher.

There will also be teaching support that will carry out additional exercises with students.
The teacher is available to the student for any clarification or explanation of the topics covered during the course.
Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/servicesstudents-physical-or-learning-disabilities
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects.

The exam consists of written exam with 10 exercises regarding the whole program and subsequent oral discussion for those who have passed the written exam. In particular, there will be 5 exercises on nomenclature (correctly write the structure of a molecule from the name IUPAC and vice versa), isomerism and resonance (assign the configurations of stereocentres and the arrangement of electrons within a molecule able to give resonance) and 5 exercises on reactivity (predict the products of a reaction), synthesis (identifying a synthetic pathway also of several steps) and reaction mechanisms (the knowledge of a reaction mechanism allows to predict the products).
Both the written and oral exam allow to evaluate the student's theoretical knowledge, his ability to write formulas and reaction mechanisms and the ability to predict the products of a reaction starting from certain reagents as well as explaining the evolution and the stereochemistry of a reaction based on its mechanism.
The passing grade is achieved by demonstrating that the student has understood the subject and is able to use the basic concepts of the topics covered during the course through the exercises. The ability to correctly write formulas and reaction mechanisms in the written exam and on the blackboard is also essential in order to pass the exam.
Other parameters of judgment are: the ability to organize and clearly expose the answer and the acquisition of the appropriate terminology (learning skills). Excellence can be achieved by demonstrating a strong ability to link-compare different topics covered during the course (making judgements).

Covalent bond, shape of the molecules. Ibridation and bond angles. Alkanes and cycloalkanes Constitutional Isomers. IUPAC nomenclature. Functional groups. Conformational isomers. Geometric isomers in cycloalkanes and alkenes. The E/Z system. Chirality. Stereoisomerism. The R,S system. Enantiomers separation. Resonance and electronic delocalization. Carbocations and carbanions. Inductive and mesomeric effects. Nucleophiles and electrophiles. Radicals and radicalic reactions. Bronsted and Lewis Acid and bases. Molecular structure and acidity. Alkanes and alkenes reactivity. Reaction mechanisms and energetic profiles. Electrophilic addition reactions. Oxidation and reduction of alkenes. Alkynes. Electrophilic addition of alogens and water. Hydrogenation. Alogenoalkanes. Nucleophilic substitution reactions SN1 e SN2. Analysis of the factors influencing the reaction rates. Elimination reactions E1 and E2. Competition between substitution and elimination reactions. Alcohols, eters and thiols. Reactivity of alcohols and ethers. Epoxides. Acid or base catalysed epoxide ring opening. Aromatic compounds. Benzene and aromaticity. Electrophilic aromatic substitution. Phenols. Oxidation in benzylic position. Nucleophilic aromatic substitution. Arendiazonium salts and their reactivity. Aldehydes and ketones. Carbonyl group structure and reactivity. Nucleophilic addition of carbanions, alcohols and amines. Reaction mechanisms. Oxidation and reduction. Keto-enol tautomerism. Alfa-substitution. Aldol condensation. Carboxylic acids and their derivatives. Reduction. Esterification. Conversion to acyl chlorides. Reaction with amines. Hydrolysis of functional derivatives. Nitriles. alfa-substitution. Malonic ester synthesis. Decarboxylation. Amines and other azo-compounds. Structure and basicity. Preparation and reactivity. Carbohydrates. Monosaccharides. Cyclic structure of monosaccharides and their reactions. Disaccharides and polysaccharides. Lipids. Triglycerids. Soaps and detergents. Steroids. Phospholipids. Amino acids, peptides and proteins. Acid-base properties of amino acids. Primary, secondary and tertiary structure of peptides and proteins. Nucleotides and nucleic acids.
The teaching material will be described and illustrated to stimulate learning skills through the integration of textbooks with material provided by the teacher.

Knowledge and understanding
Knowledge of the chemical and electronic structure of organic molecules and their implications for their reactivity.
Knowledge of the meaning of isomerism in all its declinations.
Knowledge of the main reactivity of each functional group.
Knowledge of the main reaction mechanisms.
Knowledge of the meaning of aromaticity.
Applying knowledge and understanding:
Ability to recognize functional groups in order to give the proposed molecules the correct nomenclature according to IUPAC rules.
Obtain the molecular structure from the IUPAC name and vice versa.
Recognize the stereochemistry of a molecule.
Ability to explain the course and the stereochemistry of a reaction on the basis of its mechanism.
Acquisition of knowledge and skills on the properties of the major classes of organic compounds and their chemical behavior.
Ability to discuss the possible reaction pathway according to the structure of the reagents and the reaction conditions.
Making judgements
Ability to evaluate from the structure of a compound and its similarity with the families of compounds studied which predictions can be made about its molecular properties.
Ability to interpret and rationalize organic reactions in terms of reaction mechanism and to address the study of the subject through critical and non-mnemonic learning.
Ability to connect and compare different topics covered during the course.
Communication skills
Ability to present a set of data on a family of organic compounds and connect them to the core principles of the discipline.
Ability to clearly organize and explain the answer by acquiring the appropriate terminology.
Learning skills
Ability to use teaching material for a critical and rational study.
Ability to update and expand knowledge of the discipline through the consultation of more advanced teaching texts.