Organic Chemistry and Chemistry Laboratory

A.Y. 2024/2025
9
Max ECTS
104
Overall hours
SSD
CHIM/03 CHIM/06
Language
Italian
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 Biology, together with the necessary background to work safely in a chemical laboratory.

Organic Chemistry (module)
This module aims at providing the student with the knowledge required to tackle the fundamental problems of organic chemistry, with particular emphasis on the study of the correlation between chemical properties and reactivity of organic compounds that are relevant for Biological Chemistry.

Chemistry Laboratory (module)
In particular the aim of the module is teaching students how to safely work in a chemistry lab and to acquire problem solving skills.
Expected learning outcomes
The student 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 Biological Chemistry.

Organic chemistry (module)
At the end of this specific module the student will acquire a good understanding of structure and reactivity of simple organic molecules; he/she will be able to describe reaction mechanisms and to predict on their basis the course of unknown reactions

Chemistry Laboratory (module)
At the end of this module the student will be able to recognize and use the most common laboratory glassware, acquiring awareness of the fundamental safety standards. He/she will be able to perform simple experimental procedures, also working in team, and fill out the laboratory notebook.
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

A - L

Responsible
Lesson period
Second semester
Prerequisites for admission
The knowledge of the basic topics treated in a General Chemistry course is compulsory. The notions acquired in the course "Chimica generale con Elementi di Chimica Fisica" (first semester) are taken for granted.
Assessment methods and Criteria
Organic chemistry module: students are evaluated through a written examination and an interview, both compulsory, to test their capability to recognize the reactivity of organic compounds from their structure. In the case of positive evaluation of the written examination, students must be assessed through a colloquium done in the same exam session.
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.
modulo: Laboratorio di Chimica (con Prevenzione e Sicurezza)
Course syllabus
The course will allow the acquisition of expertise of working in a chemistry laboratory and of solving stoichiometry calculations.
Lessons will point to the experiences and will concern:
· elements of risk management in a chemistry laboratory
· laboratory fundamentals
· numerical applications of solution equilibria
· principles and techniques of instrumental analysis for the compound characterization and the qualitative and quantitative analysis
Teaching methods
eacher-centered, interactive lessons, partially supported by slides presentation, and single-student laboratory experiments.
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.
Teaching Resources
M.Consiglio, V.Frenna, S.Orecchio "Il laboratorio di chimica" EdiSES.
Copy of the in-class material is available on the course web-site.
http://gsellolco.ariel.ctu.unimi.it/v3/home/Default.aspx
modulo: Chimica Organica
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.
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.
Alkynes: structure and properties. Brief introduction on the reactivity of triple bond.
Aromatic compounds. Resonance effect and the structure of benzene. Criteria for aromaticity. Electrophilic aromatic substitution: mechanism and substituent effect.
Heteroaromatic compounds. Pyrrole, pyridine, indole, imidazole.
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 (an introduction). Phenols.
Amines. Structure, nomenclature and properties. 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. Amides: structure and properties of the amide bond. Phosphoric acid esters.
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.
Carbohydrates. Structure and properties. Monosaccharides. Cyclic structure of monosaccharides. Reactions of carbohydrates. 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.
Lipids: structure, classification and properties.
Purine and pyrimidine bases. Tautomerism and hydrogen bonding. The structure of nucleosides and nucleotides.
Teaching methods
Teacher-centered, interactive lessons, supported by slides presentation. Attendance is strongly recommended.
Teaching Resources
Any good Organic Chemistry textbooks which covers exhaustively the different topics of the course.
B. Botta et al., Chimica Organica Essenziale - II Edizione, EdiErmes, Milano, 2018.
W. H. Brown, T. Poon, Introduzione alla Chimica Organica - VI Edizione, Edises, Napoli, 2020.
P. Y. Bruice, Elementi di Chimica Organica, Edises, Napoli, 2017.
H. Hart, C. M. Hadad, L. E. Craine, D. J. Hart, Chimica organica - VIII Edizione, Zanichelli, Bologna, 2019.
J. McMurry, Fondamenti di Chimica Organica - IV Edizione, Zanichelli, Bologna, 2011.

Exercises:
F. Nicotra, L. Cipolla, Eserciziario di chimica organica, Edises, Napoli, 2013.
M. V. D'Auria, O. Taglialatela Scafati, Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica, Loghìa Editore, Napoli, 2020.
B. L. Iverson, S. Iverson, Guisa alla soluzione dei problemi di Chimica organica di Brown, Iverson, Anslyn, Foote - IV Edizione, Edises, Napoli, 2016.
Janice, Gorzynski, Smith, Fondamenti di Chimica Organica, IV edizione, McGraw Hill LLC.
On Ariel website all files of (a) lessons, and (b) exercises will be available
modulo: Chimica Organica
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Practicals: 16 hours
Lessons: 40 hours
Professor: Cauteruccio Silvia
modulo: Laboratorio di Chimica (con Prevenzione e Sicurezza)
CHIM/03 - GENERAL AND INORGANIC CHEMISTRY - University credits: 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 1
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Shifts:
Turno A1
Professor: Carlucci Lucia
Turno A1+A2+A3
Professor: Di Carlo Gabriele
Turno A2
Professor: Mercandelli Pierluigi
Turno A3
Professor: Colombo Alessia

M - Z

Responsible
Lesson period
Second semester
Prerequisites for admission
In order to be able to follow the organic Chemistry course successfully, it is essential to have mastered the concepts taught in the first semester of the general Chemistry with physical Chemistry course.
Assessment methods and Criteria
The organic chemistry unit (module) consists of a written test followed by an oral examination aimed to test the student's ability to predict the properties and chemical behaviour of organic compounds.
The Chemistry Laboratory module is examined by evaluating the practical tests carried out by the student during the course.
A single mark is recorded based on the average of the marks from the two modules, weighted according to credits.
modulo: Laboratorio di Chimica (con Prevenzione e Sicurezza)
Course syllabus
The course will allow the acquisition of expertise of working in a chemistry laboratory and of solving stoichiometry calculations.
Lessons will point to the experiences and will concern elements of risk management in a chemistry laboratory, laboratory fundamentals, numerical applications of solution equilibria
principles and techniques of instrumental analysis for the compound characterization and the qualitative and quantitative analysis.
Teaching methods
Teacher-centered, interactive lessons, partially supported by slides presentation, and single-student laboratory experiments.
The inscription to this module is compulsory, it is one-year valid and it must be done exclusively in January and February (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.
Teaching Resources
M. Consiglio, V. Frenna, S. Orecchio "Il laboratorio di chimica" EdiSES.
Copy of the in-class material is available on the course web-site.
https://lco.ariel.ctu.unimi.it/
modulo: Chimica Organica
Course syllabus
Alkanes and Cycloalkanes: Structure, Isomerism, and Nomenclature. Conformational Analysis of Linear and Cyclic Alkanes. Stereochemistry: Chirality and Stereogenicity. Recognition of Constitutional Isomers, Enantiomers, and Diastereomers. Configuration Descriptors.
Alkenes: Structure and Properties. Electrophilic Addition Reactions to the Double Bond with Hydrogen Halides, Water, Halogens, Peracids, Permanganate. Hydrogenation. Allylic Systems and Their Reactivity. Brief Overview of Dienes and Terpenes. Carbocations and Their Stability.
Alkynes: Structure and Properties, and Brief Overview of Reactivity.
Aromatic Compounds: Structure and Properties. Recognition and Reactivity of Aromatic Compounds. Effect of Substituents on Aromatic Reactivity. Heteroaromatic Compounds: Structure and Properties of Pyridine, Pyrrole, Indole, Imidazole.
Alkyl Halides: Nucleophilic Substitutions and Eliminations: Classification of Reaction Mechanisms. Elimination Reactions.
Alcohols, Thiols, Ethers, and Epoxides: Structure and Properties. Hydrogen Bonding and Acidity of Alcohols. Oxidation and Dehydration Reactions. Brief Overview of Thiols and Ethers. Brief Overview of Epoxide Reactivity. Acidity and Properties of Phenols.
Amines: Structure, Properties, and Basicity. Aromatic Amines.
Carbonyl Compounds: Structure and Properties. Irreversible and Reversible Nucleophilic Additions to the Carbonyl Carbon: Reduction, Hydration, Synthesis of Acetals and Imines. Reductive Amination. Keto-Enol Tautomerism.
Carboxylic Acids and Their Derivatives: Structure and Properties. Reactivity of Acids: Conversion to Acyl Chlorides and Anhydrides, Fischer Esterification. Structure and Properties of Esters. Reactivity of Esters: Acidic and Basic Hydrolysis. Structure and Properties of Amides. Reactivity of Amides: Acidic and Basic Hydrolysis. Phosphoric Acid Esters.
Enolates of Aldehydes, Ketones, and Esters: Alpha-Carbon Acidity and Enolate Structure. Reactions with Electrophiles. Simple and Crossed Aldol Condensation. Claisen Condensation. Structure, Properties, and Synthesis of Beta-Diketones, Beta-Ketoesters, Beta-Diesters. Decarboxylation. Alpha-Carbon Acidity of These Compounds.
Carbohydrates: Structure and Properties. Monosaccharides: Acyclic and Cyclic Structures. Reactions of Monosaccharides (Overview). Formation of Glycosides and Disaccharides.
Amino Acids: Structure, Properties, and Classification Based on Side Chain Characteristics. Amino Acid Acidity and Isoelectric Point. Peptide Bond.
Lipids: Structure, Classification, and General Properties.
Nucleic Bases: Tautomeric Structures and Hydrogen Bond Formation. Structure of Nucleosides and Nucleotides (Overview).
Teaching methods
Teacher-centered, interactive lessons, supported by slides presentation. Attendance is strongly recommended.
Teaching Resources
Any valuable Organic Chemistry textbook which covers exhaustively the different topics of the course.
B. Botta et al., Chimica Organica Essenziale - II Edizione, EdiErmes, Milano, 2018.
W. H. Brown, T. Poon, Introduzione alla Chimica Organica - VI Edizione, Edises, Napoli, 2020.
P. Y. Bruice, Elementi di Chimica Organica, Edises, Napoli, 2017.
H. Hart, C. M. Hadad, L. E. Craine, D. J. Hart, Chimica organica - VIII Edizione, Zanichelli, Bologna, 2019.
J. McMurry, Fondamenti di Chimica Organica - IV Edizione, Zanichelli, Bologna, 2011.

Exercises:
F. Nicotra, L. Cipolla, Eserciziario di chimica organica, Edises, Napoli, 2013.
M. V. D'Auria, O. Taglialatela Scafati, Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica, Loghìa Editore, Napoli, 2020.
B. L. Iverson, S. Iverson, Guisa alla soluzione dei problemi di Chimica organica di Brown, Iverson, Anslyn, Foote - IV Edizione, Edises, Napoli, 2016.
Janice, Gorzynski, Smith, Fondamenti di Chimica Organica, IV edizione, McGraw Hill LLC

All files of (a) lessons, and (b) exercises will be available on the Ariel website
modulo: Chimica Organica
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Practicals: 16 hours
Lessons: 40 hours
Professor: Dal Corso Alberto
modulo: Laboratorio di Chimica (con Prevenzione e Sicurezza)
CHIM/03 - GENERAL AND INORGANIC CHEMISTRY - University credits: 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 1
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Shifts:
Turno B1
Professor: Civera Monica
Turno B1+B2
Professor: Civera Monica
Turno B2
Professor: Sattin Sara
Professor(s)
Reception:
Chemistry Dep., building 5B, 3rd floor, room 3021
Reception:
Wednesday 10:30-12:30
Chemistry Department, Side A, first floor
Reception:
By appointment by e-mail
Dipartimento di Chimica – Corpo A – Piano rialzato – Stanza R36
Reception:
by appointment
Chemistry Department, via Golgi, 19, Building 5, 3rd floor, corpo (unit) B, Room 3058B