Organic Chemistry
A.Y. 2025/2026
Learning objectives
The aim of the course is to provide students with the necessary background to understand the chemistry of organic compounds and organic reactions mechanisms that are of interest in Medical Biotechnology This course aims at providing students with the knowledge required to tackle the fundamental problems of organic chemistry, with particular emphasis on the study of the correlation between physical-chemical properties and reactivity of organic compounds
Expected learning outcomes
Students will be able to know the principles of organic chemistry and to evaluate the applications of those chemical knowledges that are basic for the study of Medical Biotechnology. They will acquire a good understanding of structure and reactivity of simple organic molecules; will be able to describe reaction mechanisms and to predict on their basis the course of unknown reactions.
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course cannot be attended as a single course. Please check our list of single courses to find the ones available for enrolment.
Course syllabus and organization
Single session
Responsible
Lesson period
Second semester
Course syllabus
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. Polarimetry. Resolution of racemates.
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, hydroboration and hydrogenation. Reactivity of allylic systems. Introduction to dienes, polyenes and terpenes.
Alkynes. Structure, nomenclature and properties. Acidity of terminal alkynes. Hydrogenation of alkynes.
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.
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. Nitriles and thioesters.
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.
Carbohydrates. Structure and properties. Monosaccharides. Cyclic structure of monosaccharides. Reactions of carbohydrates at the anomeric carbon. Formation of glycosides and disaccharides.
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. Peptide synthesis.
Heteroaromatic compounds. Pyrrole, pyridine, indole, imidazole. Purine and pyrimidine bases. Tautomerism and hydrogen bonding. The structure of nucleosides and nucleotides.
Stereochemistry. Chirality and stereogenic carbons. Configurational isomers. Enantiomers and diastereoisomers. The R, S system of nomenclature. Optical rotation and optical purity. Polarimetry. Resolution of racemates.
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, hydroboration and hydrogenation. Reactivity of allylic systems. Introduction to dienes, polyenes and terpenes.
Alkynes. Structure, nomenclature and properties. Acidity of terminal alkynes. Hydrogenation of alkynes.
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.
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. Nitriles and thioesters.
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.
Carbohydrates. Structure and properties. Monosaccharides. Cyclic structure of monosaccharides. Reactions of carbohydrates at the anomeric carbon. Formation of glycosides and disaccharides.
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. Peptide synthesis.
Heteroaromatic compounds. Pyrrole, pyridine, indole, imidazole. Purine and pyrimidine bases. Tautomerism and hydrogen bonding. The structure of nucleosides and nucleotides.
Prerequisites for admission
The knowledge of the basic topics treated in a General Chemistry course is compulsory. The notions acquired in the course "General and Inorganic Chemistry" (first semester) are taken for granted.
Teaching methods
Teacher-centered, interactive lessons, supported by slides presentation (posted before the lessons on the Ariel website of the course).
Attendance at lessons is strongly recommended
Attendance at lessons is strongly recommended
Teaching Resources
Any good Organic Chemistry textbook which covers exhaustively the different topics of the course.
Suggestions:
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
Suggestions:
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
Assessment methods and Criteria
Students are evaluated through a written examination. Once passed the written test (18/30 or more), students can ask for an oral exam to change the final grade, or accept it as it is. The test consists of about ten questions of a general nature, concerning the characteristics of organic compounds and their reactivity. The duration of the test will be two hours.
Two partial tests will be proposed, in the middle and at the end of the semester, lasting 1 hours each. Tests will focus on the part of the program carried out in the first and second part of the course, respectively; each will be structured in about ten questions similar to those of the written exam. Achieving an evaluation of 18/30 in the first test is a necessary condition for admission to the second one. If the average of the two tests is sufficient, the student may ask to record the final grade, or to modify it with an oral test.
Two partial tests will be proposed, in the middle and at the end of the semester, lasting 1 hours each. Tests will focus on the part of the program carried out in the first and second part of the course, respectively; each will be structured in about ten questions similar to those of the written exam. Achieving an evaluation of 18/30 in the first test is a necessary condition for admission to the second one. If the average of the two tests is sufficient, the student may ask to record the final grade, or to modify it with an oral test.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Lessons: 64 hours
Professor:
Raimondi Laura Maria
Professor(s)
Reception:
please contact by e-mail or phone
Dipartimento di Chimica - via Golgi 19 - Milano - building C, 2nd floor, room 2011 or via Teams