OVERVIEW

This is the first organic chemistry course for students enrolling in the Bachelor of Science degree in Chemistry and Chemical Technology. It is therefore the course in which the foundation is laid for the proper understanding of the topics that will be covered in the subsequent teachings in the same subject area. It is important that students assimilate all the concepts without gaps, so that they do not run into difficulties later in their academic careers.

AIMS AND CONTENT

LEARNING OUTCOMES

The aim of the course is to provide the student with the basic knowledge for understanding and describing the structure and reactivity of the main classes of monofunctional organic compounds. The student, who has continuously followed the course and the various classroom exercises, should have acquired the following skills: - knowing how to represent the electronic, structural and stereochemical characteristics of organic molecules - be able to assign the IUPAC name to an organic molecule of medium structural complexity - be able to qualitatively predict some chemical-physical properties of molecules, including acidity and basicity - understand and predict the reactivity of organic molecules on the basis of thermodynamic and kinetic fundamentals and on the basis of their functional groups - be able to hypothesize synthetic pathways for organic compounds of simple structure. The specific skills acquired will allow you to enrich your cultural background in the chemical field and to enhance your critical sense in solving problems

AIMS AND LEARNING OUTCOMES

Students should come to be able to recognize the main classes of organic reactions. To correctly write balanced stoichiometric equations and to evaluate the kinetic (e.g., need for catalysis) and thermodynamic (position of equilibrium) aspects of the same reactions. They will need to know how to predict the products of a given reaction. They will be able to recognize the molecular diversity of two molecules by observing their formulas. On the other hand, they will be able to correctly write organic chemistry formulas following common conventions by unambiguously identifying molecular entities. Students will be expected to be able to interpret the systematic names of molecules or assign a name to a given formula. Finally, students are expected to be able to understand and possibly clearly state all the reasoning that can explain the chemical reactivity of various classes of organic compounds

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PREREQUISITES

The fundamental concepts of General Chemistry acquired during the course of General and Inorganic Chemistry in the first semester

TEACHING METHODS

Traditional lessons in the classroom (64 hours). The solutions of problems will be treated in additional and optional tutoring hours. Gaming activities will be also offered to the students.

SYLLABUS/CONTENT

Definition of Organic Chemistry and its evolution from a historical point of view

Valence, formal charge, Lewis formulas

Different types of hybridization, VSEPR theory and molecular geometry, multiple bonds

Covalent bonding and polarity, intermolecular forces, the functional group concept

Hydrocarbons: classification and generalities

Alkanes: properties, nomenclature and constitutional isomers, stereoisomers: enantiomers and diastereoisomers, determination of absolute configuration, Fischer projections

Linear and cyclic alkanes: conformations and Newmann projections

Alkenes and alkynes: properties, nomenclature and isomeria

Conjugated polyenes: properties and interaction with UV-Vis radiation

Resonance theory: hybrids and boundary forms

Benzene and aromatic compounds: Huckel's rule, nomenclature, heteroaromatic compounds

Oxygen-containing organic compounds: classification, physical properties, nomenclature, acidity and basicity. Carbonyl compounds and the ketoenolic tautomeria

Sulfur-containing organic compounds: classification, physical properties, nomenclature, acidity and basicity

Nitrogen-containing organic compounds: classification, physical properties, nomenclature, acidity and basicity

Reactivity of organic compounds: general principles of thermodynamics and kinetics, reaction graphs, transition states, and Hammond's postulate

Terminology: definition of substitution, addition, elimination, nucleophile and electrophile

Classification of organic reactions on the basis of mechanism.

Nucleophilic substitution reactions: monomolecular and bimolecular mechanism. Carbon nucleophiles: alkyl lithium compounds and Grignard reagents

The elimination reactions: monomolecular and bimolecular mechanism. Regiochemical and stereochemical aspects. Elimination reactions as a method of oxidation of alcohols to carbonyl compounds.

Nucleophilic addition reactions: general mechanism. Synthesis of cyanhydrins, hydrated forms, hemiacetals and hemiaminals, acetals and imines. Hydride addition and reduction of carbonyl compounds to alcohols. Addition of nucleophiles to carbon, aldol condensation. Conjugate additions.

Nucleophilic addition and elimination reactions (acyl nucleophilic substitution): general mechanism. Reactivity of different carboxyl derivatives, catalyzed reactions. Fischer esterification and saponification reaction. Claisen condensation reaction.

Electrophilic addition reactions: general mechanism, Markovnikov's rule and carbocation transposition. Acid-catalyzed water addition. Addition of halogens and stereochemical implications, addition of halogens to water, addition of borane and anti-Markovnikov selectivity, regio/stereospecific and regio/stereoselective reactions, electrophilic addition reactions to alkynes: similarities and differences from alkenes

Electrophilic addition and elimination reactions: general mechanism, Wheland's intermediate. Friedel-Crafts halogenation, nitration, sulfonylation, alkylation and acylation reactions. Activating and orienting effect in substituted benzenes. Electrophilic addition and elimination reactions on heteroaromatic derivatives.

Special reactivity: oxidation and reduction reactions and calculation of oxidation number. Catalytic hydrogenation reactions and heat of hydrogenation. Reduction of C-C double and triple bonds.

Synthesis methods of the main classes of organic compounds. Alkyl halides: from alkenes, from alcohols and from carbonyl camphers (with acid and basic catalysis). Ethers: Williamson synthesis. Epoxides: from alkenes via cyanohydrins. Alcohols: from alkenes, from carbonyl campos, from alkyl halides and from epoxides. Alkenes: from alkenes, from alkyl halides and from alcohols. Alkynes: from terminal alkynes and from derivative dialogenes. Aldehydes and Ketones: from alcohols, from carboxyl derivatives, from alkynes. Carboxylic derivatives: preparation of acyl chlorides with thionyl chloride, preparation of symmetric and mixed anhydrides and cyclic anhydrides, preparation of esters and amides from acyl chlorides, anhydrides and esters, preparation of amides from nitriles and nitriles from amides. Amines: Gabriel synthesis, reduction of nitroderivatives and nitriles, reductive amination.

Radical reactions: generalities about radicals and their stability. Single electron displacement arrows. Polymerization reactions: initiation, propagation and termination. Radical polymerization of ethylene and styrene.

RECOMMENDED READING/BIBLIOGRAPHY

The program will not follow a specific book.

Anyway, students are advised to integrate the lessons with consultation of any Organic Chemistry book for chemists (that can be borrowed in the library). For example:

• J. McMurry, CHIMICA ORGANICA, Piccin
• P.Y. Bruice, CHIMICA ORGANICA, EdiSES
• M. Loudon, CHIMICA ORGANICA, EdiSES
• P.C. Vollhardt, N.E. Schore, CHIMICA ORGANICA, Zanichelli
• A.A. vari, CHIMICA ORGANICA (a cura di B. Botta), Ediermes
• Brown-Foote-Yverson-Anslyn, CHIMICA ORGANICA, Edises

For excercises:

M.V. D'Auria, O.T. Scafati, A. Zampella, Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica, Loghìa

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

From February 24th, 2025

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

Due to organizational requirements, students who intend to take the exam must strictly book at least 7 days before the date of the written test at the following link: https://servizionline.unige.it/studenti/esami/prenotazione

The exam consists of a written test and an oral test.

In the written test, students will have to answer questions on the following topics: nomenclature and isomery, acidity and basicity, general reactivity, and specific reactivity.

In particular, students will have to identify and discuss the physicochemical and stereochemical characteristics of molecules, the products of a reaction and the mechanism by which it takes place, they will have to represent the structure of simple mono- and polyfunctional molecules, hypothesize the synthetic route of simple molecules.

A maximum score will be associated with each question, which will take into account the difficulty of the question; the written test is considered passed when the overall score is at least equivalent to 18/30

Students during the written test will not be allowed to use notes or textbooks; the use of a calculator will be allowed in case there are questions that require algebraic calculations.

In order to practice, students will have available (downloadable from AulaWeb) mock exam papers and written tests from previous sessions with their solutions.

Students who pass the written proof will only be able to take the oral proof in the same exam session. The oral test will consist of a series of notional questions on the topics of the program and may include the solution of exercises from the written test that were not taken or taken incorrectly.

If the committee finds that the educational objectives of the teaching have not been met, the student will be asked to withdraw. In that case, he/she will also have to repeat the written test in a subsequent appeal. A student who, having passed the written, voluntarily withdraws from the oral test, will similarly have to repeat both tests in another session.

In the case of passing the oral test, the overall grade will be the average of the grade in the written test and the grade in the oral test.

ASSESSMENT METHODS

The assessment of achievement of learning outcomes is first done through the written test. It covers the entire course syllabus and contains questions with different levels of difficulty. It is divided into four parts: 1. Isomeria and Nomenclature 2. Acids and Bases 3. General Reactivity 4. Specific Reactivity. For each part there may be both notional questions and questions that require application of the knowledge learned; passing the test guarantees that the student has acquired at least the basics. The oral examination is able to verify with high accuracy the level of achievement of the educational objectives of the teaching by asking diversified questions pertaining to the program actually carried out during the course lectures. When the formative objectives are not met, the student is invited to check his or her knowledge more thoroughly and, if necessary, to avail himself or herself of further explanations by contacting the lecturer in charge of the teaching course.

Exam schedule

FURTHER INFORMATION

Only the students who have already successfully obtained the credits for "General Chemistry and Laboratory" will be admitted to the exam.

On the aulaweb platform, students will be able to take various assessment tests so that they can monitor/verify their preparation for the exam. These tests simulate the various parts of the written test of the exam and, if taken according to the indicated timelines, they will be able to receive feedback from the teacher. These tests, and their solutions, will still be available throughout the duration of the teaching.

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