27215 - Organic Chemistry II
Compulsory
5.1. Methodological overview
The methodology followed in this course is oriented towards achievement of the learning objectives. It favors the understanding of the different chemical processes that occur in the environment. A wide range of teaching and learning tasks are implemented, such as theory sessions, laboratory sessions, assignments, and tutorials.
Students are expected to participate actively in the class throughout the semester.
Classroom materials will be available via Moodle. These include a repository of the lecture notes used in class, the course syllabus, as well as other course-specific learning materials.
Further information regarding the course will be provided on the first day of class.
5.3. Syllabus
The course will address the following topics:
Theory sessions
Enols and enolates: Ceto-enol tautomerism. Formation of enolates. Reactivity of enols and enolates. Nitrogen analogous of enols and enolates.
Alkylation of enolates: Enolates of compounds with active methylenes. Enolates derived from other carbonyl compounds: regio- and stereoselectivity. Enamines and aza-enolates.
Reaction of enolates with aldehydes and ketones: The aldol reaction. The Mannich reaction. The Knoevenagel reaction. The enolates of esters.
Acylation of enolates: Reactions of Claisen and Dieckmann. Acylation of enolates of ketones. Other acylations.
Conjugate additon of enolates: The Michael reaction. The Robinson anulation. Other reactions of addition conjugate to a,b unsaturated carbonyls
Compounds of phosphorus: Utility in transformation of functional groups. Ylides and carbanions stabilized by phosphorus: reactions of Wittig, Wadswoth-Emmons and Horner.
Compounds of sulfur: Carbanions and ylides of sulfur in the creation of C-C bonds. Elimination giving to C=C bonds.
Compounds of silicon: Compounds with a Si-O bond. Carbanions estabilised by silicon: Peterson reaction. Compounds of organosilicon: b-effect and synthetic utility.
Reductions: Catalytic hydrogenation. Hydrides of B and Al. Reduction by dissolving metals. Reductive coupling of carbonyls.
Oxydations: Oxidation of alcohols. Epoxidation and dihydroxylation of alkenes. Oxidative cleavage of 1,2-diols and alkenes. Baeyer-Villiger oxidation.
Heterocyclic compounds: Aromatic heterocycles. p–deficient systems: pyridine. p–excedents systems : pyrrole, furan and thiophene
Carbohydrates: Structure and reactivity of monosaccharides. Glycosides and anomeric effect. Disaccharides and polisaccharides.
Amino acids, peptides and proteins: Structure and synthesis of amino acids. Peptides and proteins. Synthesis of peptides.
Polymers: Polymers of addition. Radical , anion and cation polymerization. Polymers of condensation. Properties of polymers
Laboratory sessions
Session 1. Aldol reaction
Session 2. Claisen condensation
Session 3. NaBH4 reduction
Session 4. Wittig reaction
Session 5. Synthesis of a heterocycle
Session 6. Penta-O-acetyl-D-glucose
Session 7. Preparation of nylon 6,10