Organic Chemistry Ii
A.Y. 2021/2022
Learning objectives
The course is a continuation of Organic Chemistry I and aims at providing an introduction to the chemistry of carbocyclic aromatic compounds. Additional topics include the chemistry of biologically relevant organic molecules.
Expected learning outcomes
Skills acquired by the students at the end of the course are the knowledge of the chemistry of aromatic systems as well as of some biomolecules such as carbohydrates, aminoacids, peptides. In particular, they will achieve competences in the design of the synthesis of aromatic systems, even of pharmacological interest.
Lesson period: year
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
year
More specific information on the delivery modes of training activities for academic year 2021/22 will be provided over the coming months, based on the evolution of the public health situation.
Course syllabus
Monocyclic aromatic compounds.
Benzene: principles of aromaticity, resonance, the Hückel rule. Nomenclature. Electrophilic aromatic substitution: mechanism and orientation. Halogenation, alkylation, acylation, nitration, sulfonation. Nitro compounds. Aromatic amines: synthesis and reactivity. Diazonium salts and their industrial importance. Aryl sulfonic acids. Sulfonamides. Aromatic halogen compounds: synthesis and reactivity. Nucleophilic aromatic substitution. Phenols and phenyl ethers. Fries and Claisen rearangements. Kolbe synthesis. Reaction with formaldehyde, Reimer-Tiemann and copulation reactions. Quinones. preparation and reactivity. Oxidation and reduction of aromatic compounds. Side-chain reaction: benzyl radical and carbocation.
Polycyclic aromatic compounds.
Biphenyls and atropisomerism. Fluorene and analogs. Naphthalene: synthesis, halogenations, sulfonation, nitration and Friedel-Crafts reactions. Anthracene and phenanthrene.
Heterocyclic compounds.
Classification and nomenclature. Heteroaromaticity. Synthesis and reactivity of five-membered heterocycles: pyrrole, furan and thiophene. Indole. Pyridine: structure, synthesis and properties. Pyridine N-oxide. Nucleophilic substitution. Quinoline and isoquinoline. Examples of biologically active heterocyclic compounds: pyrimidine and purine bases, nucleotides.
Amino acids and peptides.
Alpha-amino acids: structure, nomenclature, acid-base properties, isoelectric point, titration curves, stereochemistry, separation. Synthesis and resolution of amino acids. Protecting groups. Synthesis of peptides. Solid-phase synthesis.
Carbohydrates.
Classification and nomenclature. Monosaccharides: structure, stereochemistry, Fischer projections and reactivity. Cyclic hemiacetals. Mutarotation. Formation of glycosides. Reducing sugars. Oxidation and reduction. Chain lengthening and shortening. Disaccharides: sucrose, maltose, lactose. Polysaccharides.
Benzene: principles of aromaticity, resonance, the Hückel rule. Nomenclature. Electrophilic aromatic substitution: mechanism and orientation. Halogenation, alkylation, acylation, nitration, sulfonation. Nitro compounds. Aromatic amines: synthesis and reactivity. Diazonium salts and their industrial importance. Aryl sulfonic acids. Sulfonamides. Aromatic halogen compounds: synthesis and reactivity. Nucleophilic aromatic substitution. Phenols and phenyl ethers. Fries and Claisen rearangements. Kolbe synthesis. Reaction with formaldehyde, Reimer-Tiemann and copulation reactions. Quinones. preparation and reactivity. Oxidation and reduction of aromatic compounds. Side-chain reaction: benzyl radical and carbocation.
Polycyclic aromatic compounds.
Biphenyls and atropisomerism. Fluorene and analogs. Naphthalene: synthesis, halogenations, sulfonation, nitration and Friedel-Crafts reactions. Anthracene and phenanthrene.
Heterocyclic compounds.
Classification and nomenclature. Heteroaromaticity. Synthesis and reactivity of five-membered heterocycles: pyrrole, furan and thiophene. Indole. Pyridine: structure, synthesis and properties. Pyridine N-oxide. Nucleophilic substitution. Quinoline and isoquinoline. Examples of biologically active heterocyclic compounds: pyrimidine and purine bases, nucleotides.
Amino acids and peptides.
Alpha-amino acids: structure, nomenclature, acid-base properties, isoelectric point, titration curves, stereochemistry, separation. Synthesis and resolution of amino acids. Protecting groups. Synthesis of peptides. Solid-phase synthesis.
Carbohydrates.
Classification and nomenclature. Monosaccharides: structure, stereochemistry, Fischer projections and reactivity. Cyclic hemiacetals. Mutarotation. Formation of glycosides. Reducing sugars. Oxidation and reduction. Chain lengthening and shortening. Disaccharides: sucrose, maltose, lactose. Polysaccharides.
Prerequisites for admission
Organic Chemistry I
Teaching methods
Traditional
Teaching Resources
- Any comprehensive textbook of Basic Organic Chemistry
- John D. Hepworth, David R. Waring and Michael J. Waring, Aromatic Chemistry, Royal Society of Chemistry, Cambridge, 2002
- John D. Hepworth, David R. Waring and Michael J. Waring, Aromatic Chemistry, Royal Society of Chemistry, Cambridge, 2002
Assessment methods and Criteria
Written and oral examination.
The exam consists of two compulsory parts: a written test and an oral test. The written test will include problems related to all the topics discussed in the course. In the oral exam the conceptual as well as theoretical aspects of the subject will be assessed.
The exam consists of two compulsory parts: a written test and an oral test. The written test will include problems related to all the topics discussed in the course. In the oral exam the conceptual as well as theoretical aspects of the subject will be assessed.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 7
Practicals: 16 hours
Lessons: 48 hours
Lessons: 48 hours
Professor:
Speranza Giovanna
Professor(s)
Reception:
By appointment
Teacher's office - via C. Golgi 19 - 20133 Milano