OVERVIEW

Studying organic chemistry is an opportunity to investigate an exciting and vital science for everyday life. The foundations of this discipline create the basis for advanced studies in medical, biological, chemical, and materials sciences. Furthermore, using this knowledge allows us to understand some modern technologies of daily use. Through the recognition of functional groups, the three-dimensional design of molecular structures and the interpretation of the mechanical processes of reactions, the student will be able to obtain theoretical training functional to face and successfully overcome the subsequent theoretical-practical teachings, such as pharmaceutical chemistry, biochemistry, drug analysis, laboratories, etc. This training also aims to provide students with the essential elements of organic chemistry necessary for developing professional skills to engage in the work activities the future pharmacy graduate envisages

AIMS AND CONTENT

LEARNING OUTCOMES

Fundamental knowledge of organic chemistry: recognition of classes of organic molecules, identification of functional groups and basic reactivity, understanding of the structure of the main classes of natural compounds.

AIMS AND LEARNING OUTCOMES

The program aims to help understand the relationships between the structure and reactivity of the main functional groups, aromatic and heteroaromatic systems. Pupils will have to understand the fundamental principles of the chirality of organic compounds and the importance of this principle in biological systems and in the synthesis of pharmacologically active chiral substances. The mechanical study of reactions for the synthesis of model molecules will allow the student to link the reactivity of functional groups to the three-dimensional structures of the resulting compounds, preventing the student from memorizing lists of disconnected reactions. The student must develop skills in designing a multistage synthesis using acquired synthetic strategies for solving problems. Understanding and reasoning are the basis for learning the subject. Mastering organic chemistry requires a deep understanding of some fundamental principles and the ability to use these principles to analyse, classify and make predictions.

Students will be directed to the study of organic chemistry to obtain a series of skills and abilities useful for completing scientific training that will enable them to analyze, classify, explain, and predict the reactivity of organic compounds. Students will have to know the fundamental theories to be able, with reasoning, to solve organic chemistry problems. They will have to be able to argue theories, master graphic skills, and use technical and correct language to be able to demonstrate measurable learning results during the written and oral tests.

At the end of the course, students will be able to:

1. Use the periodic table to determine the electron configuration in the ground state and the bond geometries of a central atom;

2. Interpret atomistic and molecular theories to understand the strength and nature of chemical bonds;

3. Use molecular models for the determination of molecular geometries;

4. Predict the chemical nature (electrophile, nucleophile, acid and base) of an atom within a molecular structure;

5. Master the fundamental concepts of stereochemistry with the use of 3D models, visualization software and drawing chiral molecules on paper;

6. Visualize and spatially orient the substituents in a molecule as well as being able to draw the interconversion of structural representations during a multistep reaction;

7. Classify the reactivity of organic compounds and functional groups within a molecule or between different molecules;

8. Recognize the acidic or basic nature and strength of a certain compound by attributing the position of an acid-base equilibrium;

9. Recognize the electrophilicity, nucleophilicity and propensity to leave a given atom or functional group;

10. Determine the relative stability of carbocations and radicals to understand the progress of a reaction for a specific mechanism;

11. Predict whether a reaction occurs, or not, and by what mechanism;

12. Correctly draw the curved arrows to represent the flow of electrons in an ionic reaction and in radical processes;

13. Represent the resonance limit structures of a compound;

14. Understand the connections between the organic reactions studied and those that occur in nature and in cell biology.

15. The students will be able to create multimedia products (individually or in groups) using a correct scientific language.

16.The student will be able to self-evaluate their own work and evaluate other people's work through a peer-review process.

PREREQUISITES

General and inorganic chemistry 

TEACHING METHODS

The course includes 3 weekly lectures of 2 hours each, during which all the notions relating to the organic chemistry teaching program are transmitted to the students.

Teaching materials to support the lessons (presentations, exercises, and in-depth articles) are provided to students through the aulaweb platform. Fundamental texts are recommended for the study of theory and for carrying out the exercises. However, part of the lesson is carried out on the blackboard, using digital media and molecular models to educate the student in the two- and three-dimensional design of molecules and in the carrying out of chemical reactions with the relative mechanism. To face dynamic frontal lessons, the active participation of students is required in answering questions and carrying out exercises individually or in groups. Quizzes and exercises will be available on the aulaweb platform to keep the study updated, which allows a profitable accompaniment of the lessons throughout the teaching period of organic chemistry.

Activities are planned to promote the ability to peer-review and self-evaluate the papers to promote the ability to learn to learn (basic level). The production of multimedia products is encouraged to develop functional alphabetic skills that allow the student to seek and process information, present, communicate and argue theories and practical concepts in both oral and written form (basic level).

Tips on how to study: 1) keep the study of the weekly topics updated, never let them accumulate; 2) study the material in small teaching units and make sure you understand each new section before moving on to the next; 3) solve all the problems of the chapter; 4) write during the study in a theory and exercise notebook; 5) learn by teaching and explaining (study better in a group); 6) use molecular models during the study.

Any Student with documented Specific Learning Disorders (SLD), or with any special needs, shall reach out to the Lecturer(s) and to the dedicated SLD Representative in the Department ( Prof. Luca Raiteri, Luca.Raiteri@unige.it ) before class begins, in order to liaise and arrange the specific learning methods and ensure proper achievement of the learning aims and outcomes. VERY IMPORTANT: any request for compensatory tools and adaptations in the exam MUST be done within 10 working days before the date of the exam according to the instructions that can be found at https://unige.it/disabilita-dsa/comunicazioni

SYLLABUS/CONTENT

1.Elements of general chemistry: electronic structure and bonding

Structure of the atom and distribution of electrons in the atom. Covalent bonds (polar and non-polar). Representations of the structure of a compound. Atomic and molecular orbitals. Valence bond theory, VSEPR model and molecular orbital theory (TOM).Hybridization of carbon and formation of single, double and triple bonds. Hybridization of other atoms (B, O, N) and related molecular geometries. Dipole moment of a bond and dipole moment of a molecule.

2. Acids and bases: fundamental concepts in organic chemistry

Organic acids and bases. Definition of Ka and pKa. Predict the position of an acid-base equilibrium via pKa. Factors influencing the strength of an acid and its pka. Acid-base theories of Arrhenius, Bronsted-Lowry and Lewis. Use of curved arrows to represent the flow of electrons involved in an acid-base reaction.

3. Introduction to organic compounds: nomenclature, physical properties and structure

Nomenclature of alkanes and cycloalkanes, alcohols and ethers, alkyl halides and amines. Rotation around the sigma single bond (C-C). Conformational analysis of alkanes and its rotamers. Newman projection of the conformational isomers of a linear alkane. Ring tension of cycloalkanes. Conformation analysis of cyclohexane. Conformers of cyclohexanes, mono-, di- and trisubstituted. Cis-trans isomerism of cycloalkanes. Cyclohexanes condensed into decalin and steroid hormones.

4. Isomers: the arrangement of atoms in space

Constitutional isomers and stereoisomers. Cis-trans and E/Z isomerism in compounds with double bonds. Chirality concept. Chiral molecules with asymmetric center (stereogenic center). Representation of enantiomers and R,S descriptors for chiral carbons. Fischer projection. Origin of the optical activity of chiral compounds. Rotational optical power. Molecules with multiple chiral centers (diastereoisomers and meso compounds). Separation of enantiomers (racemic mixture).

5. Alkenes: structure, nomenclature and introduction to reactivity

Reactivity of alkenes and use of curved arrows. Mechanism of a reaction between a nucleophile and an electrophile. Thermodynamics and kinetics of a reaction.

6. The reactions of alkenes

Addition of water and hydrogen halides to alkenes. Stability of carbocations and radicals. Transposition of carbocations. Regioselectivity of electrophilic addition reactions (Markovnikov rule) and radical addition (anti-Markovnikov). Hydroboration-oxidation of alkenes. Addition of halogens to alkenes. Addition of a peroxyacid to alkenes (epoxidation). Addition of ozone to alkenes (ozonolysis). Stereochemistry of addition reactions to alkenes: regioselective, stereoselective or stereospecific reaction.

7. The reactions of alkynes

Nomenclature, structure and reactivity of alkynes. Electrophilic additions to alkynes: introduction to keto-enol tautomerism. Catalytic hydrogenation of alkenes and its stereochemistry. Acidity of alkynes. Use of acetylide ions in organic synthesis.

8. Electronic delocalization, resonance structures and its effect on stability, pKa

Benzene bonds, resonance boundary structures and resonance hybrid. Predicting the stability of resonance structures. Stability of dienes, allylic and benzylic cations. Effect of electron delocalization on pKa.

9. Substitution and elimination reactions of alkyl halides

Mechanism of a bimolecular (SN2) and monomolecular (SN1) nucleophilic substitution reaction. Factors influencing SN2 and SN1 reactions. Elimination reactions of alkyl halides (E2 and E1). Stereochemistry and competitions between the SN2, SN1, E2 and E1 reactions.

10. Reactions of alcohols, ethers, epoxides, and amines

Nucleophilic substitution reactions of alcohols. Elimination reaction (E1 and E2) of alcohols (dehydration). Stereochemistry of the dehydration reaction. Oxidation of alcohols. Nucleophilic substitution reactions of ethers and epoxides. Formation of cis and trans diols.

11. Reactions of carboxylic acids and derivatives of carboxylic acids

Structure, physical properties and reactivity of carboxylic acid derivatives (acyl chloride, anhydride, ester and amide).

12. Reactions of aldehydes and ketones

Reactivity of carbonyl compounds. Addition of strong and weak nucleophiles to the carbonyl carbon. Preparation of organolithium and organomagnesium compounds and relative addition to carbonyl carbon. Formation of imines and enamines. Formation of acetals and hemiacetals as protecting groups of the carbonyl group. Wittig reaction. Nucleophilic addition to ,-unsaturated aldehydes and ketones in the presence of weak (conjugated-1,4-addition) and strong (direct-1,2-addition) nucleophiles.

13. Alpha carbon reactions

Acidity of hydrogen  of carbonyl derivatives. Keto-enol tautomerism. Halogenation of carbon  of aldehydes and ketones. Kinetic and thermodynamic enolate ion formation. Alkylation of the  base-catalyzed carbon.

14. Reactions of benzene and substituted benzenes

Aromaticity criteria and Hueckel's rule. Aromaticity according to molecular orbital theory (Frost's rule). Electron donation by resonance in a substituted benzene ring. Electronic attraction by resonance from the substituted benzene ring. Electrophilic addition 1,2 and 1,4 to conjugated dienes. Aromatic heterocyclic compounds. Nomenclature of monosubstituted benzenes. Electrophilic aromatic substitution reactions (SEAr): halogenation, nitration, sulfonation, acylation and Friedel-Crafts alkylation). Chemical transformations of the substituents on the benzene ring. Effect of substituents on the reactivity of a benzene ring. Effect of substituents on the orientation of a SEAr.

15. Pentatomic and hexatomic aromatic heterocyclic compounds.

Aromaticity of pyrrole, imidazole, pyridine and pyrimidine. Heterocyclic amines of biological importance: histidine, histamine, porphyrin, purines and pyrimidines.

RECOMMENDED READING/BIBLIOGRAPHY

·       Paula Yurkanis Bruice ELEMENTI DI CHIMICA ORGANICA

·       L. Mayol, E. Bedini, N. Borbone, L. De Napoli, A: Galeone, M. Menna, G. Oliviero, G. Piccialli INTRODUZIONE ALLA CHIMICA ORGANICA DI BROWN-POON -  Ed. EdiSES

·       W. H. Brown, B. L. Iverson, E.V. Anslyn, C.S. Foote CHIMICA ORGANICA, Ed. EdiSES

·       P. Y. Bruice, CHIMICA ORGANICA, Ed. EdiSES

·       M. Loubon, CHIMICA ORGANICA  Ed. EdiSES

·       J. McMurry, CHIMICA ORGANICA, Ed. Piccin

·       R. T. Morrison, R. N. Boyd "CHIMICA ORGANICA" (Casa Editrice Ambrosiana)

·       Botta et all, CHIMICA ORGANICA, Ed. Edi-Ermes

TEACHERS AND EXAM BOARD

Exam Board

OMAR GINOBLE PANDOLI (President)

SILVANA ALFEI

GUENDALINA ZUCCARI (Substitute)

LESSONS

LESSONS START

The lessons start at the end of September following the official calendar

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

Exam schedule