Ateneo - UPO

Module Organic Chemistry
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.

Module laboratory
Students will be provided with basic knowledge on the techniques of purification, characterization and recognition of organic compounds, with particular attention to safety standards to be adopted in the laboratory.

Module Organic Chemistry
J. Clayden, N. Greeves, S. Warren, "Organic Chemistry"; PICCIN (ISBN 978-88-299-3233-7).
2) P. Yurkanis Bruice, Organic Chemistry; EdiSES.
3) Brown, Foote, Iverson, Organic Chemistry; EdiSES.
For this course, it is advisable to use one of the following exercise books: a) Student Study Guide and Solutions Manual for Organic Chemistry from W.H. Brown, B.L. Iverson, E.V. Anslyn, C.F. Foote, EdiSES (solutions of excercises presented in text 2) b) M.V. D'Auria, O. Taglialatela Scafati, A. Zampella, "Esercizi di Chimica Organica", Loghìa, Napoli, 2007.

Module Laboratory
1) Marco D’ischia, “la chimica organica in laboratorio” Piccin, Padova D. Pocar,
2) R. M. Roberts, J.C. Gilbert, S.F. Martin, “chimica organica sperimentale”, Zanichelli, Bologna
3) A.I. Vogel, “Chimica organica pratica", Ambrosiana, Milano

Module Organic Chemistry
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 judgmentsThe 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 skillsThe student must be able to use the teaching material (slides and exercises provided by the teacher, textbooks) for a detailed, critical and reasoned study.

Module laboratory
The main purpose of the course is to provide students with the knowledge of the techniques and practical skills needed to recognize, separate and purify the main organic compounds; the knowledge of the techniques and the ability to perform tests for the functional groups present in an organic compound; the ability to work in groups and to issue a laboratory report. Communication skills and self judgement: familiarize the student with the drafting of the laboratory notebook and the writing of reports concerning the activities carried out in the laboratory and the interpretation of the results obtained during the experiments. Ability to learn and autonomy: the student must demonstrate how to draw correct conclusions about the basic reactivity and functional groups of an organic substance through experimental observation and autonomy in choosing the most appropriate experimental techniques.

Module Organic Chemistry
Knowledge of the subjects taught in the General Chemistry course.

Module laboratory
Attendance of General and Inorganic chemistry laboratory.

Module Organic Chemistry
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.

Module laboratory
The lab is divided into a part of theoretical classroom lessons to which practical exercises will be followed. For each experience, the student is provided with an introductory part to the various experiments and questions that allow to underline what has been learned during the experiment.
During the course of experiences, the teacher and the tutor propose to the groups and collegially a comment and a discussion on the meaning of the operations carried out. The student should also individually prepare a lab sheet.

Module Organic Chemistry
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.

Module laboratory
The learning control in progress will be carried out through the daily control of the laboratory notebook with descriptions and comments on the laboratory experiences and the answers to the questions found in the experience card.

Module Organic Chemistry
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).

Module laboratory
In the laboratory, the organizer's ability is assessed on a daily basis, the time and space available to carry out individual experiences, complying with safety standards, the ability to collect data, and analyze the results by controlling the writing of the lab sheet. through the latest experience, the student's ability to apply the skills acquired during the course through the qualitative identification of an unknown substance will be evaluated a written exam is scheduled at the end of the course consisting of five questions between open exercises and open questions on the application of acquired theoretical knowledge applied to real cases based on those proposed at the bottom of the card of the individual experiences. An integral part
of the assessment is the drawing up of a written report on each laboratory experience to be delivered at the end of the course, aimed at evaluating the ability to collect data, critically analyze the obtained results and communicative skills. Followed by an oral presentation of the same through an interview aimed at verifying that the student has sufficient theoretical basis and has understood the meaning of the lab activities. Sufficient is achieved by demonstrating that they have acquired the basic theoretical bases of the techniques proposed and know how to apply them to solve simple problems, to have an appropriate vocabulary and to be able to expose them clearly. Excellence can be achieved by demonstrating that it has acquired the ability to critically select the best combination of isolation and purification techniques and have a precise idea of what needs to be done experimentally and how to do it in addition to a thorough drafting of final reports based on a careful observation of laboratory experiments.
The final grade will be formulated in a collegial way starting from the weighted average of the grades of the theoretical and laboratory course, considering the ability of the student to have assimilated the concepts of the two modules and to be able to apply the theoretical knowledge acquired.

Module Organic Chemistry
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. 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.

Module laboratory
The first part will allow the student to acquire the information needed to work in a chemical laboratory according to current safety standards: will be explained in detail the risks associated with the use of chemicals and the regulations relating to the use and disposal of the same. A large part of course is spent learning techniques in organic chemistry, including crystallization, TLC, distillation (simple, fractional, under reduced pressure, azeotropic, in a current of steam), extraction, sublimation, determination of melting point and boiling point of a pure substance. Each lecture will be followed by a corresponding laboratory experience. The analytical part consists of functional groups identification with confirmatory tests: the Lucas test for alcohols, Tollens test for aldehydes, bromine tetrachloride to the double bonds, Hinsberg test for amines, and iodoform test for methyl ketones. In the end, the student must identify an unknown substance through the knowledge learned. Students will conduct simple reactions: synthesis of aspirin (acetylsalicylic acid), oil of wintergreen (methyl salicylate) and the essence of banana (salicylate, isopentyl) ester hydrolysis, the reactions will be followed with thin-layer chromatography. As examples of extraction and purification of natural substances will be isolated carotenoids and chlorophylls A and B from spinach, caffeine from tea and coffee and cinnamic aldehyde from cinnamon.

Module Organic Chemistry
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 skillsAbility 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 skillsAbility 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.

Module laboratory
Knowledge and understanding skills
Knowledge of the theory underlying the techniques of separation, purification and control of the purity of organic compounds. Knowledge of
the main essays recognition of functional groups.
Ability to apply knowledge and understanding
Ability to collect data of individual experiences and correctly fill in the laboratory notebook.
Autonomy of judgment
Ability to interpret the results obtained during the experiments and to identify any mistakes made
Communicative Skills
Ability to appropriately describe, using the correct scientific terminology, the operations carried out in the laboratory be able to clearly describe the use of various concepts learned in the course.
Learning ability
Ability to read and perform an experimental procedure for purification or identification of organic compounds Ability to learn through observation
of experimental data.