The course aims to provide students with the knowledge necessary to deeply understand chemical structures, physical properties, preparations, and typical reactivity of organic compounds throughout the study of the most common functional groups. The inherent target is to highlight the role and the effect of Organic Chemistry in Natural Sciences and modern technology with particular attention to biological and naturalistic aspects as well as to problems concerning pollution and environmental sustainability. In this area, the acquired knowledge will play a crucial role in the study of the other disciplines envisaged in the CdS (Biochemistry, Physiology, Genetics). At the end of the course, the students should develop the skill and expertise to (1) recognise and comprehend the structural and physical properties of organic compounds, (2) autonomously understand and analyse the reactivity of the main classes of biomolecules, (3) use a suitable technical-scientific language in order to clearly explain and present the acquired concepts as well as to disseminate ideas, information, and explanations.
teacher profile teaching materials
The course aims to provide the student with the chemical basis of the structure, properties, and reactivity of organic molecules, as well as with the main notions for understanding the logic and principles that regulate the chemistry of natural complex systems.
Methodological skills (How to carry out):
At the end of the course, the student will be able to analyse and discuss the mechanism of the main reactions underlying Organic Chemistry, as well as to understand the importance of Organic Chemistry applied to the study of natural systems and to the development of biologically active molecules
1.Introduction to Organic Chemistry: Organic chemistry around us; Organic compounds; Functional groups; How molecules are written; Introduction to nomenclature.
2. Structure of molecules: The atomic structure. The Atomic Orbitals. Lewis's formulas; The chemical bond. The covalent bond. Three-dimensional structure and hybridization. Types of covalent bonds and Molecular Orbitals. The main elements and their links. The ionic bond. Electronegativity. Polarity of the bond and Resonance (I). Bond energy and length.
3. Stereochemistry: structural isomers. stereoisomerism; cis-trans stereoisomerism.
4. Acidity, Basicity and pKa: Solubility of organic compounds in water; pKa (definition and scale); Acidity and basicity of nitrogen compounds; Carbon acidity; Lewis acids and bases.
5. Reactivity in Organic Chemistry: Reactive species; method of breaking the chemical bond; resonance (II) and delocalization formulas; the main reactive species; electronic structure (delocalization) and stability of radicals, carbocations and carbanions; nucleophiles and electrophiles; reactions and mechanisms; catalysis; classification of reactions.
6. Nucleophilic Substitution. (SN1, SN2). Eliminations.
7. Nucleophilic Addition to Carbonyl: molecular orbitals explain the reactivity of the carbonyl; nucleophilic attack on aldehydes and ketones; hemiacetals, acetals, introduction to carbohydrates. Imines, Enamines
8. Nucleophilic Carbonyl Substitution: Carboxylic acids and derivatives; Property. Carboxylic acids (Fatty acids and soaps), Esters (Flavours, Waxes, Triglycerides, Phospholipids), Amides (Amino acids, Peptides, Proteins), Urea. Acyl halides, Anhydrides. Mechanism of Nucleophilic Acyl Substitution; Preparation of Acyl Halides, Esters and Amides.
9. Aromatic and heterocyclic compounds. Aromaticity. Benzene and arenes. Polycyclic aromatic hydrocarbons. Phenols: Acid Properties, Natural Polyphenols: Anthocyanins, Flavonoids, Gallic and Flavanolic Tannins. Aniline: Basic Properties
10. Heterocyclic compounds of biological and environmental importance. Pyridine, Pyrimidine, Purine. Tautomerie in hydroxy heterocycles. Nucleotides: Nitrogen bases, nucleosides and nucleotides, DNA / RNA, ATP / ADP / AMP, NAD and FAD.
John McMurry in “Chimica Organica”, Piccin-Nuova Libreria
Bruno Botta in “Chimica Organica” Edi-ermes
Lecture notes and bibliographical references will be provided
The teacher receives Tuesday from 17.00 to 19.00 by appointment via e-mail: tecla.gasperi@uniroma3.it
Programme
Cultural skills (Knowledge of):The course aims to provide the student with the chemical basis of the structure, properties, and reactivity of organic molecules, as well as with the main notions for understanding the logic and principles that regulate the chemistry of natural complex systems.
Methodological skills (How to carry out):
At the end of the course, the student will be able to analyse and discuss the mechanism of the main reactions underlying Organic Chemistry, as well as to understand the importance of Organic Chemistry applied to the study of natural systems and to the development of biologically active molecules
1.Introduction to Organic Chemistry: Organic chemistry around us; Organic compounds; Functional groups; How molecules are written; Introduction to nomenclature.
2. Structure of molecules: The atomic structure. The Atomic Orbitals. Lewis's formulas; The chemical bond. The covalent bond. Three-dimensional structure and hybridization. Types of covalent bonds and Molecular Orbitals. The main elements and their links. The ionic bond. Electronegativity. Polarity of the bond and Resonance (I). Bond energy and length.
3. Stereochemistry: structural isomers. stereoisomerism; cis-trans stereoisomerism.
4. Acidity, Basicity and pKa: Solubility of organic compounds in water; pKa (definition and scale); Acidity and basicity of nitrogen compounds; Carbon acidity; Lewis acids and bases.
5. Reactivity in Organic Chemistry: Reactive species; method of breaking the chemical bond; resonance (II) and delocalization formulas; the main reactive species; electronic structure (delocalization) and stability of radicals, carbocations and carbanions; nucleophiles and electrophiles; reactions and mechanisms; catalysis; classification of reactions.
6. Nucleophilic Substitution. (SN1, SN2). Eliminations.
7. Nucleophilic Addition to Carbonyl: molecular orbitals explain the reactivity of the carbonyl; nucleophilic attack on aldehydes and ketones; hemiacetals, acetals, introduction to carbohydrates. Imines, Enamines
8. Nucleophilic Carbonyl Substitution: Carboxylic acids and derivatives; Property. Carboxylic acids (Fatty acids and soaps), Esters (Flavours, Waxes, Triglycerides, Phospholipids), Amides (Amino acids, Peptides, Proteins), Urea. Acyl halides, Anhydrides. Mechanism of Nucleophilic Acyl Substitution; Preparation of Acyl Halides, Esters and Amides.
9. Aromatic and heterocyclic compounds. Aromaticity. Benzene and arenes. Polycyclic aromatic hydrocarbons. Phenols: Acid Properties, Natural Polyphenols: Anthocyanins, Flavonoids, Gallic and Flavanolic Tannins. Aniline: Basic Properties
10. Heterocyclic compounds of biological and environmental importance. Pyridine, Pyrimidine, Purine. Tautomerie in hydroxy heterocycles. Nucleotides: Nitrogen bases, nucleosides and nucleotides, DNA / RNA, ATP / ADP / AMP, NAD and FAD.
Core Documentation
T.W. Graham Solomons; Craig B. Fryhle in “Organic Chemistry”, 10th Edition, Wiley.John McMurry in “Chimica Organica”, Piccin-Nuova Libreria
Bruno Botta in “Chimica Organica” Edi-ermes
Lecture notes and bibliographical references will be provided
The teacher receives Tuesday from 17.00 to 19.00 by appointment via e-mail: tecla.gasperi@uniroma3.it
Reference Bibliography
Lecture notes and bibliographical references will be provided The teacher receives Tuesday from 17.00 to 19.00 by appointment via e-mail: tecla.gasperi@uniroma3.itType of delivery of the course
The course mainly involves lectures and a few laboratory sessions during which some basic purification, analysis and synthetic strategies frequently used in Organic Chemistry will be illustrated.Type of evaluation
Written and oral exam concerning the whole course program. Alternatively, to the final written exam, the student can sustain three midterm exams.