Ateneo - UPO

The module aims to provide: the basic concepts and language essential for the study of Organic Chemistry as well as basic elements on the nomenclature, structure and reactivity of the most common classes of organic compounds namely alkanes, alkenes and alkynes, halogen alkanes, alcohols, and ethers Aldehydes and ketones. Aromatic hydrocarbons Carboxylic acids Aliphatic and aromatic amines Aromatic aldehydes Phenols. Biomolecules. Laboratory module: students will be provided with the basics of safety rules to be adopted in the laboratory, and techniques for purification, characterization, and recognition of organic compounds.

Brown, Foote, Iverson, “Chimica Organica”, EdiSES; P. Yurkanis Bruice, “Chimica Organica”, EdiSES;
N. E. Shore, P. Vollhardt, Chimica organica, Zanichelli W.H. Brown, C.S. Foote, Chimica organica, Edises J. McMurry, Chimica organica, Piccin Broggini-Zecchi.
Guida alla soluzione dei problemi da «Introduzione alla Chimica Organica» F. S. Lee, EdiSES
"Eserciziario di Chimica Organica", F. Nicotra, L. Cipolla, EdiSES

Knowledge and Understanding. The course aims to provide the fundamentals of the chemistry of carbon compounds through knowledge of the structure and reactivity of the major functional groups, the mechanisms of the most important reactions, and the basic principles of organic stereochemistry. Ability to apply knowledge and understanding. The student will be able to apply the assimilated theoretical concepts to solve exercises in nomenclature, stereochemistry, and reactivity of organic molecules. Communication Skills. The student/student should have acquired and should be able to use appropriate chemical vocabulary concerning the topics covered and should also be able to state correctly, clearly, and concisely the mechanisms by which organic molecules react and be able to predict the products of a reaction. Autonomy of judgment The student/student should be able to predict a molecule's properties and reactivity based on the compound's structure and its similarity to the families of compounds studied. Students will also need to demonstrate the ability to compare topics developed at different times during the course. Learning ability. Students should be able to use the course material for in-depth, critical, and reasoned study. Laboratory Module The main purpose of the course is to provide students with knowledge of the techniques and practical skills needed to recognize, separate, and purify major organic compounds; the ability to work in groups, and to write a laboratory report. Communication and self-assessment skills: familiarize the students with the writing of the laboratory notebook and the writing of reports regarding the activities carried out in the laboratory and the interpretation of the results obtained during the experiments. Learning skills and autonomy: the student must demonstrate the ability to draw correct conclusions about the basic reactivity of functional groups of an organic substance through experimental observation and autonomy in choosing the most appropriate experimental techniques.

It is necessary to have acquired the topics covered in the General Chemistry course.

Lectures with multimedia aids and exercises. Slides used during the lectures will be provided to students via D.I.R. platform. In addition to the lectures, classroom exercises will be conducted by the lecturer and also with the involvement of students to deepen the topics covered in class. The concepts covered in the course will be discussed collegially in the classroom and applied directly during classroom exercises to stimulate students' critical sense and independent judgment. Communication skills will be stimulated through the use of terminology appropriate to the subject matter. Learning skills will be fostered through textbooks with materials provided by the lecturer.
Laboratory Module. The laboratory consists of theoretical lectures in the classroom followed by practical exercises in the laboratory in which students will be divided into small groups. For each experience, an introductory part to the different experiments is provided with questions and exercises aimed at testing their learning skills During the individual experiences, the teacher proposes to the groups and collegially a commentary and discussion on the meaning of the operations performed. Students will also have to draft a laboratory notebook.

Organic chemistry module. A lecturer will be available to conduct additional exercises with the students. The lecturer is available to the student(s) for any clarification or explanation of the topics covered during the course. Laboratory module Ongoing learning will be assessed through the lecturer's daily checking of the laboratory notebook with the description and comments on the experiences performed and the answers to the questions in the experience sheet.

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

Organic Chemistry Module The exam consists of a written exam of 10 exercises and subsequent oral discussion for those who passed the written test. Of the 10 exercises in the written exam, 5 exercises are on nomenclature (knowing how to correctly write the structure of a molecule from its IUPAC name and vice versa), isomerism and resonance, and 5 exercises on reactivity (knowing how to predict the products of a reaction), synthesis (identifying a synthesis route even of multiple steps) and reaction mechanisms. The focus of the oral exam will be the discussion of the written exam, and it will include questions on the reaction mechanisms explained in the lecture. Laboratory module The student's/student's ability to organize the time and space available to carry out individual experiments while complying with safety regulations, and the ability to collect data and analyze results by checking the laboratory notebook writing is assessed daily. A report is required at the end of the lab.

Course topics: Structure and properties of organic compounds
General introduction to chemical bonding. Covalent, ionic and polar covalent chemical bonding: properties and geometry. Lewis structure formulas and formal charges, resonance formulas.
Functional groups, physical properties and IUPAC. Functional groups and their influence on physical and chemical properties (acidity and basicity) Inter- and intra-molecular interactions and their effect on properties and reactivity.
Isomerism, conformational analysis, and stereochemistry. Isomeria cis, trans in cycloalkanes. Chirality and configurational analysis: diastereomery and enantiomery. E or Z configuration in alkenes. Priority rules. Enantiomers and optical activity. Planes of symmetry. Assignment of absolute R or S configuration.
Resonance and charge delocalization, Carbocation, and carbanions. Inductive and mesomer effects. Nucleophiles and electrophiles. Radical reactions and stability of radicals.

Functional groups and their reactivities Alkanes, alkenes and alkynes: Reactivity of hydrocarbons. Reactivity of alkenes. Electrophilic addition to double bonds, reaction mechanism. Markovnikov's rule and regioselective reactions. Energy diagrams, transition states, reaction intermediates. Hydration of alkenes. Radical addition of HBr. Electrophilic addition and catalytic hydrogenation. Reactions of alkenes: Bromine addition and stereochemistry. Oxidation and reduction of alkenes. Epoxidation and concerted mechanism. Stereospecific reactions. Oxidation. Catalytic hydrogenation. Hydroboration-oxidation. Alkynes: IUPACs, synthesis and reactivity. Keto-enolic tautomeria.
Alkyl halides: Alkyl halides: synthesis and reactivity. Unimolecular and bimolecular nucleophilic substitution (SN1, SN2). Effects of th substrate, nucleophile (basicity-nucleophile relationship), leaving group, and the solvent. Mono- and bimolecular elimination reaction. Competition with SNS. Alcohols: chemical and physical properties. Acidity and basicity, formation of alkoxides. Synthesis by reduction. Oxidation. Dehydration. Transformations to alkyl halides.
Ethers: properties, synthesis and cleavage. Epoxides. Epoxide ring opening in acidic and basic environments with stereochemistry. Thiols: acidity and basicity; reactivity, oxidation-reduction. Amines: synthesis, reactivity, alkylation, reduction of amides. Aldehydes and ketones: structure, properties and preparation. Nucleophilic addition to carbonyl. Addition of water, alcohols with formation of acetals. Nucleophilic addition of amines, reductive amination. Addition of Grignard reagents to carbonyl. Reduction and oxidation. Tautomeria and condensation reactions. Carboxylic acids and acyl nucleophilic substitution reactions: Carboxylic group acidity, preparation and reactions. Derivatives of carboxylic acids: Synthesis of derivatives (acyl chlorides, anhydrides, esters, thioesters, amides). Hydrolysis, alcoholysis. Amides: aminolysis, mesomery and tautomery. Acyl phosphates. Reduction of carboxylic acid derivatives and Grignard addition. Keto-enolic tautomeria and enolization.
Acidity of hydrogens in alpha to carbonyl. Aldolic condensation, Claisen, Dieckmann. Michael's reaction.

Benzene: aromaticity, nomenclature and properties. Benzene reactivity: aromatic electrophilic substitution: halogenation, nitration, sulfonation, alkylation and acylation. Effects of substituents on disubstitution: activation and orientation. Oxidation at the benzyl position. Reduction of nitrobenzene. Trisubstituted benzenes and effects of substituents. Phenols and aromatic amines. Aromatic nucleophilic substitution. Radical reactions. Amino acids and peptides: classification and acid-base properties. Definition of zwitterion and isoelectric point. Peptide bonding, mesomery, and properties. Sugars: Fischer projections, D,L notation, anomeric carbon, and glycosidation reaction. Definition of epimer. Cyclic monosaccharides, mutarotation. Reduction to alditols. Oxidation, esters, and ethers. Disaccharides: lactose, sucrose, maltose. Polysaccharides. Lipids: fatty acids, waxes, and triacylglycerols. Saponification of fats. Phospholipids and cell membrane. Steroids.

The student is expected to demonstrate adequate knowledge and understanding of the topics covered in the course, with particular emphasis on a proper grasp of the logic of Organic Chemistry. The student is expected to be able to apply knowledge and skills in dealing with even complex problems with sufficient autonomy of judgment. Laboratory Module. Knowledge and ability to understand. Knowledge of the theory behind the techniques of separation, purification, and purity control of organic compounds. Ability to collect data from individual experiments and fill out the laboratory notebook. Ability to perform simple laboratory operations: knowing how to choose the right equipment to assemble a reaction, and separate and purify a substance. Autonomy of judgment: Ability to interpret the results obtained in the experiments. Communication skills: Ability to appropriately describe, using the correct scientific terminology, the operations carried out in the laboratory through the daily writing of the laboratory notebook and final report. Learning skills: Ability to read and perform an experimental procedure and to learn through observation of experimental data.