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
Stereochemistry: isomers and stereoisomers. Inductive and Resonance effects.
The main reaction mechanisms: electrophilic addition to alkenes, dienes and alkynes. Polymerizations. Electrophilic aromatic substitution on benzene and heteroatoms present in biological molecules. Addition to carbonyls and nucleophilic substitution of acyls. Enolates and their condensations. Bi- and polyfunctional molecules: hydroxy acids, enonic systems, ketoacids. Physico-chemical properties of amino acids (structures and isoelectric point). Carbohydrates (classification, hemiacetal structures, glucosides, polysaccharides).
Nucleophilic substitution (SN1, SN2) and elimination (E1 and E 2) at sp3 carbon. Acetacetic and malonic synthesis. Redox reactions on organic compounds. Radical reactions of hydrocarbons (combustion and radical oxidation) using model reaction (halogenation).
J. Mc Murry Chimica Organica Ed. Piccin
pdf notes of lessons are available to students on Moodle
Programme
Hybridization of carbon. Functional groups: structure, nomenclature (IUPAC and use) and chemical-physical properties of alkanes, cycloalkanes, alkenes, alkynes, arenes, halides, alcohols, thiols, ethers, sulphides, amines, aldehydes, ketones, imines, phenols, carboxylic acids, esters, lactones, amides, imides and nitriles.Stereochemistry: isomers and stereoisomers. Inductive and Resonance effects.
The main reaction mechanisms: electrophilic addition to alkenes, dienes and alkynes. Polymerizations. Electrophilic aromatic substitution on benzene and heteroatoms present in biological molecules. Addition to carbonyls and nucleophilic substitution of acyls. Enolates and their condensations. Bi- and polyfunctional molecules: hydroxy acids, enonic systems, ketoacids. Physico-chemical properties of amino acids (structures and isoelectric point). Carbohydrates (classification, hemiacetal structures, glucosides, polysaccharides).
Nucleophilic substitution (SN1, SN2) and elimination (E1 and E 2) at sp3 carbon. Acetacetic and malonic synthesis. Redox reactions on organic compounds. Radical reactions of hydrocarbons (combustion and radical oxidation) using model reaction (halogenation).
Core Documentation
W. H. Brown, B.L. Iverson, E.V. Anslyn, C.S. Foote Organic ChemistryJ. Mc Murry Chimica Organica Ed. Piccin
pdf notes of lessons are available to students on Moodle
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.Attendance
Continuous and active attendance is highly recommended. Attendance of lab experiences is compulsory.Type of evaluation
Learning verification takes place through a written test and a subsequent oral exam. During the course, in itinere tests will be supplied to allow direct access to the oral examination. All written tests contain 4 exercises, aimed at verifying the level of comprehension of the reaction mechanisms and of chemical compounds reactivity and the students' ability to evaluate their application on a given substrate in the presence of specific reaction conditions. Exam tests (and in itinere tests) from previous years are available on the course website. teacher profile teaching materials
Part 2: an introduction to 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 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 illustratedType of evaluation
Written and oral exam concerning the whole course program. Alternatively, to the final written exam, the student can sustain three midterm exams