Saturated hydrocarbons: alkanes and cycloalkanes. Structure, nomenclature and properties. Isomerism: structural isomers and conformers. Conformational analysis.
Stereochemistry. Chirality and stereogenic carbons. Configurational isomers. Enantiomers and diastereoisomers. The R, S system of nomenclature. Optical rotation and optical purity.
Haloalkanes and substitution and elimination reactions. Nucleophilic substitution at saturated carbon atoms: rates, mechanism (SN1, SN2), stereochemistry. Elimination reactions (E1, E2).
Alcohols, thiols, ethers and epoxides. Structure, nomenclature and properties. Acidity of alcohols. Oxidation and elimination reactions. Reactivity of epoxides.
Amines. Structure, nomenclature and properties.
Alkenes. Structure, nomenclature and properties. The E, Z system of nomenclature. Reaction of alkenes: ionic addition of H-X (Markovnikov's rule): hydration; halogenation, oxidation and hydrogenation. Reactivity of allylic systems. Introduction to dienes, polyenes and terpenes.
Aromatic compounds. Resonance effect and the structure of benzene. Criteria for aromaticity. Electrophilic aromatic substitution: mechanism and substituent effect. Phenols and aromatic amines.
Carbonyl compounds. Structure, nomenclature and properties. Nucleophilic addition of hydrides, water, alcohols and ammonia derivatives. Oxidation and reduction reactions. Keto-enol tautomerism.
Carbohydrates. Structure and properties. Monosaccharides. Cyclic structure of monosaccharides. Reactions of carbohydrates at the anomeric carbon. Formation of glycosides and disaccharides.
Carboxylic acids and derivatives. Structure, nomenclature and acidity of carboxylic acids. Synthesis of acyl chlorides, anhydrides, esters. Esters: properties and reactions. Acid- and base-catalyzed hydrolysis of esters. Reactions with ammonia derivatives. Amides: structure and properties of the amide bond. Phosphoric acid esters. Thioesters.
Amino acids. Classification and properties of amino acids. Configuration of amino acids. Acid-base properties of amino acids. The isoelectric point. Peptide bond and peptides conformation.
Enolates: acidity at the alpha-position of aldehydes, ketons and esters. Alkylation of enolates. The aldol condensation. The Claisen condensation. Structure and properties of beta-diketons, beta-ketoesters and malonic esters. The decarboxylation reaction. Biosynthesis of fat acids.
Heteroaromatic compounds. Pyrrole, pyridine, indole, imidazole. Purine and pyrimidine bases. Tautomerism and hydrogen bonding. The structure of nucleosides and nucleotides.
Readings and Course Material
Organic Chemistry Module
Any good Organic Chemistry textbook which covers exhaustively the different topics of the course.
W. Brown, T. Poon, Introduzione alla Chimica Organica, Edises, Napoli
P. Y. Bruice, Elementi di Chimica Organica, Edises, Napoli
P.Y. Bruice, Organic Chemistry, Prentice Hall, Inc., New Jersey
J. McMurry, Chimica Organica - un approccio biologico, Zanichelli, Bologna
B. Botta e altri Chimica Organica Essenziale, EdiErmes, Milano
J.G. Smith Fondamenti di Chimica Organica, McGraw Hill Education, Milano
Exercises can be found on line:http://ariel.unimi.it/User/Default.aspx
- Chimica Organica: esercizi on-line (section 2)http://lraimondico.ariel.ctu.unimi.it/v3/home/Default.aspx
The knowledge of the basic topics treated in a General Chemistry course is compulsory.
Organic chemistry module: students are evaluated through a written examination and a colloquium, both compulsory.
In the case of positive evaluation of the written examination, students must be assessed through a colloquium done in the same exam session. Both written and colloquium regard the whole program of the course.
Laboratory module: students are evaluated on the basis of the knowledge and the skill acquired performing the experiments
The final course-grade is a weighted average of the two modules evaluations.
The notions acquired in the course "Chimica generale con Elementi di Chimica Fisica" (first semester) are taken for granted.
Language of instruction
Mode of Teaching
Teacher-centered, interactive lessons, partially supported by slides presentation.
Single-student laboratory experiments.
Program information and Attendance Policy
Organic Chemistry Module: it is strongly recommended that students attend class regularly from the beginning of the term and meet all requirements set by the instructor.
Laboratory Module: the inscription to this module is compulsory, it is one-year valid and it must be done exclusively in november-december (check on course web-site). All students will then be convened on a fixed day for the laboratory rotations assignment: absent students will be considered renunciative.
Attendance at all scheduled laboratory lessons and experiments is compulsory. When a student misses a laboratory lesson/experiment because of an illness or unanticipated event, it is the student's responsibility to notify the instructor. In the case of documented short-term absence due to illness or other unanticipated circumstance, instructors should provide reasonable effort to accommodate the student in a way that maintains the integrity of the class.
Course website /http://lraimondico.ariel.ctu.unimi.it/v3/home/Default.aspx