Organic chemistry and chemistry laboratory

A.Y. 2020/2021
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.
Course syllabus and organization

A - L

Responsible
Lesson period
Second semester
The course will be held in the second semester 2020/21, hopefully without limitations due to the health emergency. Otherwise, lessons and exercises will be online, both in synchronous and asynchronous mode. The laboratory activities will be provided in a reduced version (if possible) or replaced with online exercises. The assessment methods for the Organic Chemistry module will not vary. For the Chemistry Laboratory module, however, if it will not be possible to conduct experimental activities, the assessment will be made with a test based on the content of the theoretical lessons and exercises
Prerequisites for admission
The knowledge of the basic topics treated in a General Chemistry course is compulsory.
Assessment methods and Criteria
Organic chemistry module: students are evaluated through a written examination and a colloquium, 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. Both written and colloquium regard the whole program of the course.
Lab module: Evaluation of the laboratory practices done by the student along the course.
The final exam mark is composed by weighted average of the two evaluations on the base of the corresponding number of credits: (org.chem x 6/9) + (Lab x 3/9).
modulo: Laboratorio di Chimica (con Prevenzione e Sicurezza)
Course syllabus
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.
Teaching methods
Teacher-centered, interactive lessons, partially supported by slides presentation.
Single-student laboratory experiments.
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.
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.
Teaching methods
Teacher-centered, interactive lessons, partially supported by slides presentation.
Single-student laboratory experiments.
Teaching Resources
Organic Chemistry Module
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
modulo: Chimica Organica
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Practicals: 16 hours
Lessons: 40 hours
Professor: Passarella Daniele
modulo: Laboratorio di Chimica (con Prevenzione e Sicurezza)
CHIM/03 - GENERAL AND INORGANIC CHEMISTRY - University credits: 0
CHIM/06 - ORGANIC CHEMISTRY - University credits: 0
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Professor: Rossi Sergio
Shifts:
Turno A1
Professor: Rossi Sergio
Turno A1+A2
Professor: Rossi Sergio
Turno A2
Professor: Rossi Sergio

M - Z

Responsible
Lesson period
Second semester
The course will be held in the second semester 2020/21, hopefully without limitations due to the health emergency. Otherwise, lessons and exercises will be online, both in synchronous and asynchronous mode. The laboratory activities will be provided in a reduced version (if possible) or replaced with online exercises. The assessment methods for the Organic Chemistry module will not vary. For the Chemistry Laboratory module, however, if it will not be possible to conduct experimental activities, the assessment will be made with a test based on the content of the theoretical lessons and exercises.
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
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 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.
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.
Teaching methods
Teacher-centered, interactive lessons, partially supported by slides presentation. Attendance 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
Exercises can also be found on line:
https://sbernasconicoe.ariel.ctu.unimi.it/v5/home/Default.aspx
https://lraimondico.ariel.ctu.unimi.it/v5/home/Default.aspx
modulo: Chimica Organica
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Practicals: 16 hours
Lessons: 40 hours
modulo: Laboratorio di Chimica (con Prevenzione e Sicurezza)
CHIM/03 - GENERAL AND INORGANIC CHEMISTRY - University credits: 0
CHIM/06 - ORGANIC CHEMISTRY - University credits: 0
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Shifts:
Turno B1
Professor: Carlucci Lucia
Turno B1+ B2+B3
Professor: Raimondi Laura Maria
Turno B2
Professor: Rizzato Silvia
Turno B3
Professor: Rizzato Silvia
Educational website(s)
Professor(s)
Reception:
please contact by e-mail or phone
Dipartimento di Chimica - via Golgi 19 - Milano - building C, 2nd floor, room 2011