Organic Chemistry
A.Y. 2024/2025
Learning objectives
Aims of the course is to present all classes of organic compounds , describing their chemico-physical characteristics, the reactivity as well as some preparation method. Knowledge of carbohydrates, amino acids, and nucleotides will be increased.Particular attention is dedicated to stereochemistry, with the recognition of chiral molecules and assessments of their reactivity.
Expected learning outcomes
The main purpose of the course is to enable the student to recognize the class of belonging of every organic molecule and thus to predict its reactivity in the biological field as well. In addition, the course provides the minimum cognitive tools for predicting or explaining supramolecular interactions among organic molecules.
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.
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. Nitriles and 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. Peptide synthesis.
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.
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.
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. Nitriles and 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. Peptide synthesis.
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.
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, partially 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
Exercises can also be found on Ariel website of the course and at the link:
https://sbernasconicoe.ariel.ctu.unimi.it/v5/home/Default.aspx
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 Ariel website of the course and at the link:
https://sbernasconicoe.ariel.ctu.unimi.it/v5/home/Default.aspx
Assessment methods and Criteria
Students' acquired knowledge is verified through a written test. An oral test may be requested by the teacher as well as by the student - once he or she has passed the written test with sufficient evaluation - should he or she wish to change the outcome.
The written test is designed to ascertain the student's ability to reason about the characteristics of organic compounds by predicting their reactivity based on structure, and consists of 10-15 general questions regarding the characteristics of organic compounds and their reactivity. The duration of the test will be two hours.
During the course, two written iteration tests will be offered, the first one about halfway through the course and the second one at the end, both consisting of 10-15 questions on the program covered and lasting two hours. Only students who have achieved a passing grade in the first test will be admitted to the second iteration test. If both tests are found to be sufficient, the average of the two assessments will be offered as the final grade, thus replacing the final written exam.
The written test is designed to ascertain the student's ability to reason about the characteristics of organic compounds by predicting their reactivity based on structure, and consists of 10-15 general questions regarding the characteristics of organic compounds and their reactivity. The duration of the test will be two hours.
During the course, two written iteration tests will be offered, the first one about halfway through the course and the second one at the end, both consisting of 10-15 questions on the program covered and lasting two hours. Only students who have achieved a passing grade in the first test will be admitted to the second iteration test. If both tests are found to be sufficient, the average of the two assessments will be offered as the final grade, thus replacing the final written exam.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Lessons: 64 hours
Professor:
Raimondi Laura Maria
Shifts:
Turno
Professor:
Raimondi Laura MariaProfessor(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