The student goal is to develop skills to understand the chemical processes underlying cellular metabolism and the vital functions of living organisms. At the end of the course, the student must be able to identify the functional groups present in natural molecules and to know their physico chemical- characteristics and the reactivity at the base of their transformations.
To this end, the course aims to provide:
- information on the structure, nomenclature and physico-chemical properties of the main organic functional groups;
- skills to recognize the stereochemistry of molecules knowing how to correlate it with the spatial structure of asymmetric carbons;
- knowledge of the structure / activity relationships and of the main organic chemistry reactions with particular regard to the mechanism of functional groups formation and
transformation and to the stereochemistry of products deriving from reactions on chiral substrates.
To this end, the course aims to provide:
- information on the structure, nomenclature and physico-chemical properties of the main organic functional groups;
- skills to recognize the stereochemistry of molecules knowing how to correlate it with the spatial structure of asymmetric carbons;
- knowledge of the structure / activity relationships and of the main organic chemistry reactions with particular regard to the mechanism of functional groups formation and
transformation and to the stereochemistry of products deriving from reactions on chiral substrates.
teacher profile teaching materials
The main reaction mechanisms: substitution and radical addition; electrophilic addition; polymerization; nucleophilic substitution (SN1, SN2) and elimination (E1 and E 2) at sp3 carbon. Aromatic electrophilic substitution. Addition to carbonyls and nucleophilic substitution to acyls. Enolated and their inter-, intra-molecular and cross-linked condensations. Bi- and polyfunctional molecules: acetacetic and malonic synthesis; hydroxy acids, enonic systems, alpha-amino acids (structures and isoelectric point), carbohydrates (classification, hemiacetal structures, glucosides, polysaccharides). Homo- and hetero-aromatic compounds.
J. Mc Murry Chimica Organica Ed. Piccin
Slides shown in the lessons are available in the professor website
Programme
Structural theory. Isomerism and stereoisomeries. Resonance and electronic effects. The functional groups: structure, nomenclature (IUPAC and use) and chemical-physical properties of alkanes, cycloalkanes, alkenes, alkynes, arenes, halides, alcohols, thiols, ethers, sulfides, amines, aldehydes, ketones, imines, phenols, carboxylic acids, esters, lactones, amides, imides and nitriles.The main reaction mechanisms: substitution and radical addition; electrophilic addition; polymerization; nucleophilic substitution (SN1, SN2) and elimination (E1 and E 2) at sp3 carbon. Aromatic electrophilic substitution. Addition to carbonyls and nucleophilic substitution to acyls. Enolated and their inter-, intra-molecular and cross-linked condensations. Bi- and polyfunctional molecules: acetacetic and malonic synthesis; hydroxy acids, enonic systems, alpha-amino acids (structures and isoelectric point), carbohydrates (classification, hemiacetal structures, glucosides, polysaccharides). Homo- and hetero-aromatic compounds.
Core Documentation
W. H. Brown, B.L. Iverson, E.V. Anslyn, C.S. Foote Organic ChemistryJ. Mc Murry Chimica Organica Ed. Piccin
Slides shown in the lessons are available in the professor website
Type of delivery of the course
The course is based on lectures using pwp presentations and some videos. Exercises and tests will be supplied and solved in class to ease the comprehension. In the event of an extension of the health emergency from COVID-19, all the provisions governing the methods of carrying out the teaching activities will be implemented. The course will take place online on the Microsoft Teams platform.Type of evaluation
Examinations take place through a written test lasting 3 hours and a subsequent oral exam. Three in itinere tests are conducted during the course which allow direct access to the oral examination. All written tests contain 4 exercises, aimed at verifying the level of understanding of the mechanisms and reactivity of chemical compounds and the students' ability to evaluate their application on a given substrate in the presence of specific reaction conditions. Examination tests (and in itinere tests) of previous years are available in the professor's website. In the event of an extension of the health emergency from COVID-19, all the provisions governing the methods for carrying out the student assessment will be implemented. In particular, an online written and oral test will be adopted. teacher profile teaching materials
Part 2: an introduction to the organic chemistry laboratory. purification and separation techniques: crystallization, extraction, distillation and chromatography (adsorption, distribution, ionic exchange, affinity); mention of HPLC gas-chromatography. practical experiences in the laboratory: polarimetry, maleic to fumaric acid isomerization, separations by extraction, nucleophilic substitution, TLC and column chromatography, esterification.
John McMurry in “Chimica Organica”, Piccin-Nuova Libreria
Bruno Botta in “Chimica Organica” Edi-ermes
Lecture notes and bibliographical references will be provided
Programme
Part 1: structural theory. isomers and stereoisomers. resonance and electronic effects. functional groups: structure, nomenclature (IUPAC and common names) and chemical-physic properties for alkanes, cycloalkanes, alkenes, alkynes, arenes, halides, alcohols, thiols, ethers, sulfides, amines, aldehydes, ketones, acetals, imines, phenols, carboxylic acids, esters, lactones, amides, imides and nitriles. homo- and hetero-aromatic compounds. main reaction mechanisms: radical substitution and addition, electrophilic addition; polymerization; nucleophilic substitution (SN1, SN2) and elimination (E1, E2) at sp3 carbon; aromatic electrophilic substitution; nucleophilic addition and substitution at carbonyl carbon. synthesis and reactivity of functional groups in view of reaction mechanisms. enolates and their inter-, intra-molecular and cross condensations. di- and poly-functional molecules: acetoacetic and malonic synthesis, hydroxy acids, enonic systemsPart 2: an introduction to the organic chemistry laboratory. purification and separation techniques: crystallization, extraction, distillation and chromatography (adsorption, distribution, ionic exchange, affinity); mention of HPLC gas-chromatography. practical experiences in the laboratory: polarimetry, maleic to fumaric acid isomerization, separations by extraction, nucleophilic substitution, TLC and column chromatography, esterification.
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
Type 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.