OVERVIEW

The study of organic chemistry is an opportunity to discover an exciting and vital science. The foundations of this discipline create the basis for subsequent studies in the medical, biological, chemical and materials sciences. Furthermore, the use of this knowledge allows us to understand some modern technologies in everyday use. Through the recognition of functional groups, the three-dimensional design of molecular structures and the interpretation of the mechanistic processes of reactions, the student will be able to obtain theoretical training useful to deal with and successfully overcome subsequent theoretical-practical teachings, such as pharmaceutical chemistry, biochemistry, drug analysis, organic chemistry laboratory, etc. This training also has the aim of providing students with the basic elements of organic chemistry necessary for the development of professional skills to be engaged in the work activities that the future pharmacy graduate envisages.

AIMS AND CONTENT

LEARNING OUTCOMES

The course aims to provide and make students learn the logical and systematic tools necessary to achieve a basic knowledge of the structure, physical characteristics, reactivity, mechanistic action and preparation of the main functional groups of organic chemistry, as a platform to address the subsequent Organic II course.

AIMS AND LEARNING OUTCOMES

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

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

Use the periodic table to determine the ground state electronic configuration and bond geometries of a central atom;
Interpret atomistic and molecular theories to understand the strength and nature of chemical bonds;
Predict the chemical nature (electrophile, nucleophile, acid and base) of an atom within a molecular structure;
Master the fundamental concepts of stereochemistry and draw chiral molecules on paper;
Visualize and orient the substituents in a molecule in space as well as being able to represent the structural variations during a multistage reaction;
Classify the reactivity of organic compounds and functional groups within a molecule or between different molecules;
Recognize the nature and acid or basic strength of a given compound by attributing the position of an acid-base balance;
Recognize the electrophilicity, nucleophilicity and propensity to exit of a given atom or functional group;
Determine the relative stability of carbocations and radicals to understand the progress of a reaction for a specific mechanism;
Predict whether a reaction occurs or not and by what mechanism;
Correctly draw the curved arrows to represent the flow of electrons in an ionic reaction and in radical processes;
Represent the resonance limit structures of a compound;
Understand the connections between the organic reactions studied and those that occur in nature and in cellular biology.

PREREQUISITES

Having passed the general and inorganic chemistry exam.

TEACHING METHODS

The teaching includes 3 weekly frontal lessons of 2 hours each during which the entire program is covered.

The teaching materials to support the lessons (presentations, exercises and in-depth articles) are provided to students through the aulaweb and/or Teams platform. Fundamental texts are recommended for studying the theory and carrying out the exercises. Part of the lesson is carried out on the blackboard. Chemical reactions with the relevant mechanism are also carried out. To approach the lessons dynamically, 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 and/or Teams platform to keep the study updated which allows for profitable accompaniment of the lessons throughout the period of organic chemistry teaching, without having an evaluation purpose on the part of the teacher.

Tips on how to study:

1) keep the study of 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 each chapter before moving on to the next;

4) write during the study in a theory and exercise notebook;

5) learn by teaching and explaining (study better in groups);

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.

4. Isomers: the arrangement of atoms in space

Constitutional isomers and stereoisomers. Geometric isomerism (cis-trans and E/Z) 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).

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.

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). Addition of hydrogen to alkenes (catalytic hydrogenation). 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 limit structures and resonance hybrid. Predicting the stability of resonance structures. Stability of dienes, allyl and benzyl 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.

13. Alpha carbon reactions

Alpha hydrogen acidity of carbonyl derivatives. Keto-enol tautomerism. Halogenation of the alpha carbon of aldehydes and ketones. Kinetic and thermodynamic enolate ion formation. Alkylation of the base-catalyzed alpha carbon. Stork reaction.

 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. 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.

RECOMMENDED READING/BIBLIOGRAPHY

Paula Yurkanis Bruice, Elements of Organic Chemistry, Ed. EdiSES

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

End of September: first available day according to the teaching calendar, barring unforeseen circumstances.

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

Written exam with open and/or multiple choice questions.

A correction phase will be introduced for your written exam following the solution to the exercises carried out by the teacher on the blackboard. Self-evaluation encourages reflection on one's own work for responsible self-correction. After the correction, the students will be informed of the score obtained and they will be able to ask for explanations.

Those who obtain a pass will proceed to the oral test.

ASSESSMENT METHODS

The written exam will include purely theoretical questions or organic chemistry exercises to be completed in two hours.

The control tools provided in the teaching and examination methods, which accompany the teaching-learning process, are aimed at ascertaining the levels of knowledge, skills and competences achieved by the students.