SM/0117 - ORGANIC CHEMISTRY 2
Academic Year 2021/2022
Free text for the University
ANDREA PORCHEDDU (Tit.)
- Teaching style
- Lingua Insegnamento
|[60/58] CHEMISTRY||[58/10 - Ord. 2017] CHIMICA||6||48|
This intermediate organic chemistry course focuses on the study of reactions of bifunctional groups and interactions of polyfunctional compounds. Topics include classical and advanced technologies to form new C-C bonds. The student also gets an introduction to
carbohydrates, proteins and nucleic acids. In addition, the activities described allow the students to acquire the methodological tools for continue their studies and to face more specialized courses.
The student shall have successfully completed the Organic Chemistry 1 exam. Good knowledge of the theories of chemical bond and structure of organic compounds. Good knowledge of physical and chemical properties of mono-functional organic compounds (contents of Organic Chemistry I).
-Notes on some fundamental concepts of organic chemistry 1. Keto-Enol tautomerism and reactions of enolate anions. Aldol reaction. Claisen and Dieckmann condensation. Acetoacetic ester and malonic ester synthesis. Conjiugate addition to a,ß-unsaturated carbonyl compounds. Michael
addition of enolate anions. Crossed enolate reactions using LDA. Enamines: alkylation and acylation reactions.
-Organometallic reactions: Reactions of transition metals for preparation of new carbon-carbon bonds. The Heck and Suzuki reactions.
-Carbohydrates. Structure and nomenclature. Mutarotation. Reaction of monosaccharides: reduction, oxidation. Oxidation by periodic acid. Acylation and Alkylation of Monosaccharides.
Osazone Formation. Chain Elongation: the Kiliani–Fischer Synthesis. Chain Shortening: the Ruff Degradation . Stereochemistry of Glucose: The Fischer Proof. . The Anomeric Effect
-Amino acids: Chirality and Acid-base properties. Reaction of an amino-acid with Ninhydrin. Resolution of Racemic Mixtures of Amino Acids. Amino and carboxyl -Protecting groups and carboxyl activation. Peptide bond forming reactions.
lectures (48h) accompanied by exercises aimed at strengthening the theoretical foundations; direct involvement of students in the development of theoretical subjects and exercises. The lessons are held using Power Point slide.
Verification of learning
The final examination will consist in a oral test.
1. J. Clayden, N. Greeves, S. Warren, "Organic Chemistry", Second edition, Oxford 2012;
2. B. Botta, “Chimica Organica”, Ed. Edi.Ermes, Milano (ISBN 9788870513271);
3. P. Y. Bruice, “Chimica Organica”, Ed. EDISES, Napoli;
4. J. G. Smith, “Chimica Organica”, Ed. McGraw-Hill, Milano;
5. J. McMurry, “Chimica Organica”, Ed. PICCIN, Padova;
6. Francis A. Carey, Richard J. Sundberg: “Advanced Organic Chemistry – Part B: Reactions and
Synthesis”, fourth edition; Kluwer Academic/Plenum Publishers.
All lecture presentations (PowerPoint slides) were made available to students.