CHIMICA ORGANICA CHIM/06 LEZIONI 64 ANDREA MEZZETTA
Learning outcomes
Knowledge The student who completes the course successfully will be able to demonstrate a good ability to recognise the functional groups of a given organic compound and to give correct prevision of its stereochemical features as well as its chemical reactivity towards the principal kinds of reagents (acids and bases, electrophiles and nucleophiles, oxidants and reductants). He or she will acquire knowledge of the mechanistic aspects of the basic organic reactions. A particular relevance will be assigned to the knowledge of the basic chemistry of the most relevant molecules related to the biotransformations.
Assessment criteria of knowledge
For the assessment of the knowledges, ongoing written tests will be carried out. In particular:
knowledge of functional groups in organic molecules
knowledge of main organic reactions knowledge of tridimensional features of organic molecules capability of connecting topics from different sections of the course
Skills At the end of the course the student will acquire and/or develop:
knowledge to pass the exam, and capability and learining methods to keep himself/herself updated within the organic chemistry area knowledge of the functional groups present in organic compounds, of their reactivity and of the reaction mechanisms
Assessment criteria of skills
During the course, exercize-based lessons will be carried out, and the student is required to prove:
to have acquired the capability to solve organic chemistry problems
to have acquired the capability to interconnect charateristics/reactivity of different types of organic compounds
Behaviors At the end of the course the student will acquire and/or develop:
the capability to analyze an organic molecule (including bio/macromolecules)
the capability to solve organic chemistry problem
Assessment criteria of behaviors
The behaviour verification will be carried out: during the assessment exercises aimed at evaluating the student’s behaviour in response to the problems posed by the teacher.
Prerequisites To fruitfully attend the Organic Chemistry course, the following knowledges are requested:
Inorganic Chemistry (chemical bonds, thermodinamics and kinetics).
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Teaching methods Delivery: face to face Learning activities:
attending lectures participation in discussions individual study Attendance: Advised Teaching methods:
Syllabus Alkanes and Cycloalkanes: IUPAC Nomenclature, constitutional isomers, alogenation reaction and alkanes combustion. Stereochemistry: conformational analysis . Geometric isomerism (cis and trans). Conformational analysis of cyclohexane. Chirality: tridimentional representation and Fischer projection, optical rotatory power. Racemates. Absolute configuration: priority rules of Chan, Ingold and Prelog. The D,L system: the glyceraldehyde. Enantiomers, diastereomers, meso compounds. Alkenes, alkynes and dienes: the C=C double bond: physico-chemical properties and IUPAC nomenclature. E/Z isomeris. Electrophilic addition to the double bond: mechanism and stereochemistry (HX, X2, H2O, H2, Markovnikov's rule). Thermodinamic stability of alkenes. Alkynes: structure and reactivity. Conjugated and nonconjugated dienes: stabililty and reactivity. Aromatic compounds: Benzene: resonance energy, Nomenclature and the Huckel rule. Reactivity: Electrophilic aromatic substitution, characteristics and mechanism. Haloakane: Substitution and eliminatin reactions. SN2 and SN1 reactions: mechanism, stereochemistry. E1 and E2 reactions: Saytzeff rule. SN2/E2 and SN1/E1 ratio. Importance of the nucleophile and of the solvent on the reaction outcome. Amines: nomenclature, proprieties. Basicity of amines. Comparison between aliphatic and aromatic amines (aniline). Other aromatic compounds: pyridine, pyrimidine, pyrrole, furan, thiophene and imidazol. Reactivity. Alcohols, phenols and ethers: Nomenclature, physico-chemical properties. Reactivity of alcohols: conversion in haloalkanes, in alkenes, oxidation. Polyalcohols. Phenols: acidity (influence of electron withdrawing substituents on the ring). Oxidation of polyphenols. Ethers: structures and their use as solvents. Aldehydes and ketones: Nomenclature physico-chemical properties; electronic structure of the carbonyl group. Nucleophilic addition reaction (H2O, ROH, HCN, NH3). Stability of imine, hydrazones and oximes. Catalytic oxidation and reduction. Identification of the carbonyl functional group. Keto-enol tautomerism. Aldol condensation. Carboxylic acids and their derivatives: nomenclature, physico-chemical properties. Salts of carboxylic acids. Derivatives of carboxylic acids: acyl halides, anhydrides, esters and amides. Acyl nucleophile substitution: mechanism and reactivity rate of carboxylic acid derivatives. Acyl chlorides: preparation and use in the synthesis of esters and amides. Esters: Fisher esterification, acid and basic hydrolysis. Identification of the functional group. Triglycerides: structures and properies. Lactones. Amides: basicity, preparation and acid hydrolysis. Terpenes: structure: isoprenic unit. Properties. Amino acids and peptides: Structure and stereochemistry. Isoeletric point . Peptides: features of the peptidic bond. Primary, secondary and tertiary structure of proteines. Carbohydrates: Classification and stereochemistry, D and L series, Common structures of aldoses and ketoses. Fischer and Haworth representation. Monosaccharides and polysaccharides. Reducing and non-reducing sugars (Feheling and Tollens reactions). Oxidation and reduction reactions of monosaccharides. Nucleic acids: general structures and DNA and RNA components: nucleosides and nucleotides.
Bibliography
Russo, G. Catelani, L. Panza, P. Pedrini, Chimica Organica, 2a Ed. Casa Editrice Ambrosiana, Milano, 1998. Botta e altri, Chimica Organica Essenziale, Edi.Ermes Milano 2012 (ISBN 978-99-7051-354-7) Catelani, F. D’Andrea, Esercizi Chimica Organica, Pisa, 2000. McMurry, Fondamenti di Chimica Organica, 4° Ed.Italiana Zanichelli, Bologna 2011. Hart, D.J. Hart, L.E. Craine, Chimica Organica, 6a Ed. Italiana, Zanichelli, Bologna, 2008. Y. Bruice, Elementi di Chimica Organica, 1° Ed. EdiSES 2017
Non-attending students info
Not-attending students can follow the lessons using the teaching material provided on the E-learning web site by the teacher, and consulting the lesson log.
Assessment methods In the written exam (based on combined theoretical questions and excercises; 2,5 hours), the student must demonstrate his/her knowledge of the course material and his/her ability to organise a correctly written reply. The oral exam, to be made to the teacher, and to other members of the exam jury as well as to the other students, will be directed to demonstrate his/her ability to give a complete and mature overview of a specific topic of the course. Methods:
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