66992 - Organic Chemistry (M-Z)

Learning outcomes

After completing the course, the student will have the knowledge necessary to the understanding and use of the main organic compounds in the level of classification, structure and properties. The student also acquires the main concepts useful for the interpretation of the reactivity of organic compounds. Finally, through simple experiments of preparation and isolation of organic compounds, the student completes and builds their knowledge of basic organic chemistry, also useful to the understanding of biological compounds.

Course contents

1. Structure and Properties of Organic Molecules - Electronic structure of the atom. Atomic orbitals. Molecular orbitals and the covalent bond. Hybrid orbitals and the formation of complex molecules. Polarity and electronegativity. Nucleophiles and electrophiles.

2. Functional Groups and IUPAC Nomenclature - The concept of functional groups in organic chemistry. Structural features of the most common functional groups: alkanes, alkenes, alkynes, alkyl halides, alcohols, thiols, ethers, amines, aromatic hydrocarbons, aldehydes, ketones, carboxylic acids, and their derivatives (acyl halides, anhydrides, esters, amides). The IUPAC system for naming organic compounds.

3. Alkanes and Cycloalkanes - Saturated hydrocarbons and molecular formulas. Structure and constitutional isomerism. Nomenclature. Physical and chemical properties. Staggered and eclipsed conformations of alkanes. Newman projections. Cycloalkanes: structure and nomenclature. Cyclohexane: conformations and conformational mobility. Cis–trans stereoisomerism in disubstituted cycloalkanes.

4. Stereochemistry - Stereoisomerism (enantiomers and diastereomers) - Stereocenters and molecular chirality. Configuration and R/S descriptors. Fischer projections. Molecules with two stereocenters and meso compounds. Properties of stereoisomers. Racemic mixtures. The significance of chirality in biological systems.

5. Alkenes - Unsaturated hydrocarbons. Structure and nomenclature. Double bonds and restricted rotation. Cis–trans . (E/Z) isomerism and relative stability of isomers. Physical and chemical properties. Introduction to organic reactions: bond formation, homolytic and heterolytic reactions, reaction mechanisms, potential energy diagrams and reaction coordinates, exothermic and endothermic reactions, transition states, intermediates, and activation energy. Electrophilic addition to alkenes: general mechanism, Markovnikov's rule, and relative stability of carbocations. Addition of hydrogen halides. Acid-catalyzed hydration. Stereochemical aspects of addition reactions. Catalytic hydrogenation: syn addition. Conjugated dienes. Heat of hydrogenation. Resonance: rules and resonance structures.

6. Alkynes - Structure and nomenclature. Brønsted acids and bases. Electrophilic addition reactions. Addition of hydrogen halides. Acid-catalyzed hydration. Keto–enol tautomerism. Acidity of terminal alkynes. Factors affecting the acidity of organic compounds. Acetylide anion reactions and applications in organic synthesis.

7.Alkyl Halides - Structure, properties, and nomenclature. Preparation by radical halogenation of alkanes. Radical chain mechanisms: initiation, propagation, and termination. Radical addition of HBr to alkenes in the presence of peroxides. Radical geometry and relative stability. Nucleophilic substitution reactions. Nucleophiles and nucleophilic substitution of alkyl halides. SN2 and SN1 mechanisms. Factors favoring SN2 and SN1 reactions. β-Elimination reactions: dehydrohalogenation of alkyl halides. Regioselectivity (Zaitsev's rule). E1 and E2 mechanisms. Competition between substitution and elimination.

8. Alcohols, Thiols, Ethers, and Epoxides - Alcohols: structure, nomenclature, physical and chemical properties. Comparison of alcohols and thiols. Reactions of alcohols. Substitution with hydrogen halides. Acid-catalyzed dehydration of alcohols: regioselective formation of alkenes. Oxidation state of organic compounds. Oxidation and reduction reactions. Oxidation of alcohols. Ethers: structure and nomenclature. Epoxides: synthesis by oxygen addition to alkenes. Structure, ring strain, and nomenclature. Reactivity of epoxides. Sulfides and disulfides.

9. Aromatic Compounds - Benzene: resonance energy and stabilization. Criteria for aromaticity. Hückel's rule. Examples of aromatic and non-aromatic compounds. Aromatic heterocyclic compounds. Effect of aromaticity on the pKa of selected compounds. Acidity of phenol. Reactions of benzene. Electrophilic aromatic substitution: general mechanism. Lewis acids and bases. Halogenation. Nitration. Sulfonation. Friedel–Crafts alkylation and acylation. Substituted benzenes: nomenclature. Effects of substituents on electrophilic aromatic substitution: reaction rate and orientation.

10. Aldehydes and Ketones - Structure and nomenclature. Reactivity of the carbonyl group. Nucleophilic addition to carbonyl compounds. Organometallic compounds. Grignard reagents. Addition of acetylide ion, cyanide ion, primary amines (imine formation), and alcohols (acetal formation). Reduction and oxidation of the carbonyl group.

11. Carboxylic Acids - Structure and nomenclature. Physical properties: dimer formation, boiling point, solubility, hydrophobic and hydrophilic regions. Acidity, inductive and resonance effects. Reactions with strong bases and solubility of carboxylate salts.

12. Carboxylic Acid Derivatives - Structure and nomenclature of acyl halides, anhydrides, esters, and amides. General mechanism of nucleophilic acyl substitution. Comparison with nucleophilic addition. Relative reactivity of carboxylic acid derivatives. Ester hydrolysis.

13. Reactions at the α-Carbon of Carbonyl Compounds - Acidity of the α-carbon. Reactivity of enolates. Aldol condensation. Crossed aldol condensation.

14. Carbohydrates - General structure and classification. Fischer and Haworth projections. D- and L-series. Cyclic structure and hemiacetal formation. Mutarotation of glucose. Conformations of monosaccharides. Reactions of monosaccharides: acetal formation, reduction, oxidation (reducing sugars). Disaccharides: cellobiose, maltose, lactose, and sucrose. Polysaccharides: cellulose and starch.

15. Amines - Nomenclature, classification, structure, and properties. Basicity of aliphatic and aromatic amines. Chemical structure of nitrogenous bases, nucleosides, and nucleotides.

16. Amino Acids - General structure. Basic and acidic amino acids. Zwitterionic structure and isoelectric point. Peptides. The peptide bond. Introduction to proteins.

17. Lipids - Introductions. Fats and oils. Soaps. Phospholipids. Steroids. Biological membranes.

18. Laboratory Exercises - Application of laboratory techniques for the extraction, synthesis, and identification of organic compounds.

Readings/Bibliography

Brown, Iverson, Ansylyn, Foote - Chimica Organica - EdiSES

P.Y. Bruice – Chimica Organica - EdiSES

J. McMurry - Fondamenti di Chimica Organica - Zanichelli

J.G. Smith – Fondamenti di Chimica Organica – McGraw Hil

H. Hart, C. M. Hadard, L.E. Craine, D.J. Hart - Fondamenti di Chimica Organica - Zanichelli

Teaching methods

Lessons and discussion.

Classroom exercises.

Practical laboratory training.

Considering the types of activities and teaching methods adopted, to attend this training activity, all students are required to carry out Modules 1 and 2 in e-learning modality [https://www.unibo.it/it/servizi-e-opportunita/salute-e-assistenza/salute-e-sicurezza/sicurezza-e-salute-nei-luoghi-di-studio-e-tirocinio] and to partecipate to Module 3 for the specific training on safety and health in study places.

Information on dates and methods of attendance for the Module 3 can be consulted in the specific section of the course of study web site.

Assessment methods

Written and oral exam on the theoretical and laboratory program carried out.

 

Students with learning disorders and\or temporary or permanent disabilities: please, contact the office responsible (https://site.unibo.it/studenti-con-disabilita-e-dsa/en/for-students) as soon as possible so that they can propose acceptable adjustments. The request for adaptation must be submitted in advance (15 days before the exam date) to the lecturer, who will assess the appropriateness of the adjustments, taking into account the teaching objectives.

Teaching tools

PowerPoint video projection

Organic chemistry laboratory and instruments for practical training

Office hours

See the website of Paola Franchi