Learning Objectives The course is based on the study of the nomenclature, reactivity and preparation of organic compounds in general and heterocyclic compounds in particular, with continuous reference to the physico-chemical properties for pharmaceutical applications The ability to recognize the functional groups, the understanding of the reaction mechanisms and the critical evaluation of the stereochemical aspects represent the main aims of the course.
The primary learning outcomes will be:
- knowledge and understanding of the reactivity of organic molecules such as acids, bases, electrophiles and nucleophiles;
- knowledge of the different types of chemical reactions;
- the ability to understand and critically discuss the mechanism of reactions;
- the ability to predict and critically discuss the stereochemistry of reaction products
- - ability in designing organic compounds from the molecular structures to the three-dimensional representations.
The primary learning outcomes will be:
- knowledge and understanding of the reactivity of organic molecules such as acids, bases, electrophiles and nucleophiles;
- knowledge of the different types of chemical reactions;
- the ability to understand and critically discuss the mechanism of reactions;
- the ability to predict and critically discuss the stereochemistry of reaction products
- - ability in designing organic compounds from the molecular structures to the three-dimensional representations.
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.
Introduction to Organic Chemistry: Organic chemistry around us; Organic compounds; Functional groups; How molecules are written; Introduction to nomenclature.
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.
Stereochemistry: structural isomers. stereoisomerism; cis-trans stereoisomerism.
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.
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.
Nucleophilic Substitution. (SN1, SN2). Eliminations.
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
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.
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
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.
P.Y. Bruice in " Chimica Organica", EdiSES
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
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.
Introduction to Organic Chemistry: Organic chemistry around us; Organic compounds; Functional groups; How molecules are written; Introduction to nomenclature.
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.
Stereochemistry: structural isomers. stereoisomerism; cis-trans stereoisomerism.
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.
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.
Nucleophilic Substitution. (SN1, SN2). Eliminations.
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
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.
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
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
David Klein in "Organic Chemistry", WileyP.Y. Bruice in " Chimica Organica", EdiSES
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
Type of delivery of the course
The course mainly involves lectures and a few laboratory sessions during which some primary purification, analysis and synthetic strategies frequently used in Organic Chemistry will be illustrated.Attendance
Lectures in the classroom and laboratory experiencesType of evaluation
The course assessment methods comprise six examination sessions, each consisting of a written examination that serves as a prerequisite for an oral examination. The written component, lasting three hours (alternatively divided into two in-course assessments), encompasses four tasks, each subdivided into multiple parts, designed to evaluate the depth of understanding of the studied concepts and the knowledge of reaction mechanisms and processes. A minimum score of 15 out of 30 is required to pass the written examination. During the oral assessment, the instructor will discuss the outcomes of the written examination and assess the knowledge acquired by the student throughout the entire examination syllabus. The final grade will be determined based on various criteria: the depth and quality of knowledge demonstrated on the subject matter, the ability to apply theories and concepts to diverse contexts, the use of appropriate scientific language relevant to Organic Chemistry, active participation during lectures and laboratory exercises, the reasoning capacity exhibited during the examination, and the ability to engage in independent study of the prescribed texts. A satisfactory knowledge of the topics presented in the syllabus is required to pass the examination at the minimum level. To achieve the highest grade of 30 out of 30 with distinction, the student must demonstrate an outstanding comprehension of all topics, linking them logically and coherently, and exhibiting confidence and fluency within the subject matter. The instructor is amenable to organising potential rescheduling of the oral examinations for each session listed on the GOMP platform, thereby accommodating student requests and enabling them to optimise their examination outcomes.