CHIMICA ORGANICA

Educational Objectives

The Organic Chemistry course aims to provide students with:

Theoretical knowledge

1. Understanding the fundamental concepts of organic chemistry:

• Structure and bonding in organic molecules.
• Polarity, resonance and reactivity of the main classes of organic compounds.
• Principles of stereochemistry and isomerism.

2. The ability to analyze the most common reaction mechanisms, with particular reference to substitution, elimination and addition reactions.

3. A basic knowledge of the principles of sustainable chemistry and related techniques applied to organic chemistry.

Practical skills

4. The ability to apply theoretical notions to solve problems and exercises related to:

• Stereochemical configurations (E/Z, R/S).
• Analysis of reaction mechanisms and prediction of basic reaction products.
• Comparison between traditional and sustainable methods in organic syntheses.

5. The ability to calculate sustainability parameters (E-factor, atom economy) for basic organic reactions and to design eco-friendly syntheses.

Transversal skills

6. The development of a critical approach to the use of solvents, reagents and catalysts, with attention to environmental impact and safety.

7. The ability to interpret experimental data related to practical exercises, correlating theory and practice.

Expected results

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

• Describe the structure and reactivity of organic molecules.
• Analyze reaction mechanisms, predicting products and intermediates.
• Propose strategies to reduce the environmental impact of chemical reactions.
• Solve complex problems related to organic chemistry and apply sustainable methodologies in syntheses.

In reference to the so-called Dublin Descriptors, the learning outcomes of the course are:

D1 - Knowledge and understanding - The student must demonstrate mastery of basic knowledge related to organic chemistry. The student must rationalize the property-structure correlations; in particular, he/she must be able to recognize the functional groups of organic molecules, their main physical properties and understand their chemical behavior.

D2 - Ability to apply knowledge and understanding - The student must be able to apply the knowledge acquired in an appropriate and flexible way in order to develop, by adopting chemical symbols, the synthesis reactions of relatively complex organic molecules.

D3 - Autonomy of judgment - The student must demonstrate critical reasoning skills and, through the knowledge acquired during the course, must schematically and appropriately identify the most suitable solutions for the synthesis of organic molecules.

D4 - Communication skills - The student must be able to communicate clearly and with an adequate and rigorous chemical language the notions acquired during the course.

D5 - Learning skills - The student must demonstrate that he/she has developed good learning and in-depth skills on the topics of the course in order to easily face the subsequent study paths.

These skills, as far as possible, will be stimulated by the teacher by proposing in-depth studies and carrying out exercises in the classroom during the course.

To guarantee equal opportunities and in compliance with the laws in force, interested students can ask for a personal interview in order to plan any compensatory and/or dispensatory measures, based on the didactic objectives and specific needs.

Co-teaching: prof. Vincenzo Cunsolo and prof. Rosaria Saletti.

Classroom Lectures (42 hours)
Classroom Exercises (45 hours)

Power Point Slides can be downloaded by Studium

Student reception hours: every morning. Due to possible overlap with institutional and non-institutional commitments, it is always advisable to send an advance email.

Introduction to carbon chemistry. Atomic orbitals. Electronic configuration of atoms. Lewis representations. The octet rule. The chemical bond. Covalent bonds and the Pauling electronegativity scale. Resonance theory. The chemical bond according to quantum mechanics: σ and π bonds. Hybrid sp3, sp2, sp orbitals. Classification of organic compounds and functional groups. Representation of molecules on the plane and in space. Molecular models. Acid-base reactions.

Introduction to organic compounds: Nomenclature, chemical-physical properties and structure.

Alkanes. IUPAC nomenclature of alkanes. Constitutional isomerism and conformational isomerism.

IUPAC nomenclature of other compounds containing sp3 hybridized carbons: alkyl halides, alcohols and amines. Non-covalent intermolecular interactions. Cycloalkanes. Ring strain and geometric cis-trans isomerism of cycloalkanes. Comparison between the structure of cycloalkanes and that of monosaccharides. Combustion reaction.

Stereoisomerism. Chirality. Asymmetric carbon. Stereocenters. Enantiomerism. Optical activity. Polarimeter. Relative configuration and absolute configuration. The stereodescriptors R and S: Cahn, Ingold and Prelog priority rules. Three-dimensional representation methods of molecules: Fisher projections. Stereoisomers with two or more asymmetric C atoms. Diastereomers and meso compounds. Biological importance of chirality. What does the resolution of a racemic mixture mean.

Alkenes. Structure and nomenclature. Geometric isomerism in alkenes and cycloalkenes: cis-trans and E-Z nomenclature. Physical properties. Alkenes in nature. Alkenes in industry. Notes on dienes, trienes and polyenes. Reactivity of the carbon-carbon double bond. The electrophilic addition reaction in alkenes (hydrogen halides, water, halogens): mechanism, carbocations, regioselectivity and Markovnikov's rule. Oxidation and reduction reactions. Addition of borane to alkenes: hydroboration-oxidation. Addition of ozone to alkenes: ozonolysis. Industrial synthesis of ethylene.

Alkynes. Structure and Nomenclature. Reactivity of the carbon-carbon triple bond. The electrophilic addition reaction in alkynes (hydrogen halides, water, halogens). Acidity of terminal alkynes: acetylides. Reduction reactions.

Alkyl halides. Reactions of alkyl halides. Aliphatic nucleophilic substitution: SN1 and SN2 mechanisms. Factors that influence the reaction mechanism: substrate, leaving group, solvent and nucleophile. The β-elimination reaction: E1 and E2 mechanisms. Factors influencing E1 and E2 mechanisms. Stereochemistry of substitution and elimination reactions. Competition between substitution and elimination reactions.

Radicals

Formation, nature, stability and structure of radicals. Chlorination and bromination of alkanes. Principle of reactivity-selectivity. Addition of radicals to alkenes. Notes on radical polymerizations in the industrial field with traditional and green methods.

Reactions of alcohols, ethers, epoxides, amines and sulfur-containing compounds. Structure, nomenclature and properties of ethers, epoxides and sulfur-containing compounds. Notes on diols and glycols. Reactivity of the alcohol group: Formation of salts, acidity and basicity. Reaction with metals, reactions with halogen acids (SN2 and SN1), reaction with SOCl2 and PBr3 and acid-catalyzed dehydration (E1 and E2). Regioselectivity and stereoselectivity. Oxidation of primary and secondary alcohols with classical and green approaches (Swern and Dess-Martin oxidation). Notes on reactivity: diols, glycols, ethers, epoxides, thiols and sulfides. Reactivity of amines: Basicity, nucleophilicity, elimination reaction. Amines. Structure and nomenclature. Physical properties. Basicity. Reactivity. Reactions of amines with nitrous acid. Reactions of diazonium salts. Diazocopulation. Azo dyes. Comparison with sustainable dyes of natural origin. Hofmann elimination. Cope elimination.

Carbonyl and carboxylic compounds.

Aldehydes and ketones. Structure. Nomenclature. Chemical-physical characteristics of the carbonyl group. Reactivity. Nucleophilic addition reactions: addition of alcohols, water, HCN. Addition of primary amines: formation of Schiff bases. Oxidation. Reduction of carbonyl compounds. Keto-enol tautomerism and acidity of hydrogens in alpha to carbonyl: principles of aldol condensation. The carbonyl group in nature: monosaccharides, disaccharides and polysaccharides. Aldehydes in the perfume industry.

Carboxylic acids. Structure and nomenclature. Physical properties. Acidity. Reactions of carboxylic acids: Reduction, Decarboxylation. Fischer esterification. Reaction with thionyl chloride. Industrial synthesis of acetic acid. Functional derivatives of carboxylic acids. Acyl halides, esters, anhydrides, amides, nitril: structure and nomenclature. Reactivity. Nucleophilic acyl substitution reaction. Hydrolysis reactions of carboxylic acid derivatives. Reduction reactions. Carboxylic acids and derivatives in nature (fatty acids, triglycerides, amino acids and proteins). Carboxylic acid derivatives in industry.

Fundamentals of Sustainable Chemistry

Introduction to green chemistry: 12 principles of green chemistry.

Evaluation of the environmental impact in the main organic chemistry reactions.

Examples of industrial uses of green chemistry.

Exercises (examples)

1. Nomenclature

• Assigning the name of an organic compound based on the given structure and vice versa.

2. Stereochemistry and Isomerism

• Solving exercises on E/Z and R/S configurations.
• Conformations of cycloalkanes: energy analysis.

 Reactions and Basic Mechanisms

• Problems on reaction mechanisms.
• Reactivity analysis: influence of solvents, bases, acids, nucleophiles, electrophiles and leaving groups.

Green approaches in Practical Problems

• Calculation of the atom economy for common organic reactions.
• Exercises on green metrics (E-factor).
• Design of simple syntheses with sustainable methods. 

1) William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric Anslyn -  Organic Chemistry - Cengage Learning (VI Edition)

2) Thomas N. Sorrell - Solutions to Exercises, Organic Chemistry - Univ Science Books

The final exam consists of a written test and an oral test. The written test, usually lasting 2 hours, consists of carrying out exercises and questions relating to the nomenclature of organic compounds, basic concepts, the reactivity of the various classes of organic compounds, and stereochemistry. The oral test (which generally takes place a few days after the written test, and in any case always within the same session) consists of a discussion of the written test and is aimed at verifying the knowledge and skills acquired by the student, his ability to connect the various topics covered with current issues and his ability to use appropriate language in presenting the proposed topics.

The evaluation is expressed at the end of the two tests. Passing the written test (suitability) allows access to the oral test which, if evaluated positively, will give rise to the final grade of the exam. The following parameters will be taken into account in assigning the final grade:

Grade 29-30 cum laude: the student has an in-depth knowledge of all the topics covered in class, is able to promptly and correctly integrate and critically analyze the situations presented, independently solving even highly complex problems; has excellent communication skills and property of language.

Grade 26-28: the student has a good knowledge of all the topics covered in class, is able to integrate and analyze the situations presented in a critical and linear way, is able to solve complex problems quite independently and exposes the topics clearly using appropriate language;

Grade 22-25: the student has a fair knowledge of the basic concepts of organic chemistry, even if limited to the main topics; is able to integrate and analyze the situations presented in a critical but not always linear way and exposes the topics quite clearly with a fair command of language;

Grade 18-21: the student has minimal knowledge of all the topics covered in class, has a modest ability to integrate and critically analyze the situations presented and presents the topics in a sufficiently clear way although the language skills are poorly developed;

Exam failed: the student does not possess the minimum required knowledge of the main contents of the course. The ability to use the specific language is very poor or non-existent and he/she is not able to independently apply the knowledge acquired.

The learning assessment may also be carried out electronically, if conditions require it.

Exercises and questions related to the nomenclature of organic compounds, basic concepts, the reactivity of various classes of organic compounds and stereochemistry.