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ORGANIC CHEMISTRY AND PREPARATORY BIOVHEMISTRY

Academic year and teacher
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Versione italiana
Academic year
2019/2020
Teacher
PAOLO MARCHETTI
Credits
10
Curriculum
BIOTECNOLOGIE PER L'AMBIENTE
Didactic period
Secondo Semestre
SSD
CHIM/06

Training objectives

The target of the organic chemistry and propaedeutics biochemistry course are based on the ability to recognize the functional groups of the various classes of organic compounds, their reactivity and the interactions these can have with biological systems. The student should also learn the structure and functional characteristics of the main types of organic macromolecules of biological interest.

Prerequisites

Basic concepts of General and Inorganic Chemistry.

Course programme

GENERAL CHEMISTRY CONCEPTS
1) The language of chemistry: atomic structure: electrons, protons, neutrons. The nucleus, atomic and mass numbers. Molecular orbitals, electronic configuration and position in the Periodic Table.
2) Mole: absolute and relative atomic masses, molecular mass, formula weight, Avogadro number. Mole concept, quantitative meaning of formulae and chemical equations.
3) Inorganic nomenclature: from the formula to the name and vice versa.
4) Chemical bond: covalent, ionic, hydrogen bond, dative, weak bonds. Hydrophobic interactions. Electronegativity. Bond order: simple, double and triple bonds. Lewis structures.
5) Hybridization, VSEPR
6) Resonance.
7) Solutions: kind of solutions, solubility. Concentration: ways to express concentration. Aqueous solutions. Preparation of solutions and dilution problems.
8) Chemical reactions: acid-base, redox. Balancing, stoichiometric ratios, excess/defect of reagent, limiting reagent, yield. Equivalent and normality.
9) pH. Acids and bases: definitions, strength, dissociation constants and grade. Polyprotic acid, salt hydrolysis, buffer solutions.
10) d-Block elements: some examples mainly related to coordination chemistry.

MAIN CLASSES OF ORGANIC COMPOUNDS
1) Alkanes. Nomenclature, natural sources and physical properties. Reactions. Geometric isomerization in cycloalkanes.
2) Alkenes. Nomenclature, natural sources and physical properties, preparations and reactions. Geometric isomerization.
3) Alkynes. Nomenclature, natural sources and physical properties, preparations and reactions.
4) Alkyl halides. Nomenclature, natural presence and physical properties, preparations and reactions, with particular attention to the mechanism of SN1, SN2, E1 and E2 reactions. Concept of leaving group and nucleophile. Environmental impact of halogenated compounds.
5) Alcohols. Nomenclature, natural sources and physical properties, preparations and reactions. Notes on thiols.
6) Aldehydes and ketones. Nomenclature, natural sources and physical properties, preparations and reactions.
7) Carboxylic acids and their derivatives. Nomenclature, natural sources and physical properties, Preparation and reactions of acids, esters, amides and acyl halides. Notes on nitriles, anhydrides and active esters.
8) Aromatic compounds. Nomenclature, natural sources and physical properties, preparations and reactions. Introduction of groups by Electrophilic Aromatic Substitution.
9) Amines. Nomenclature, natural sources and physical properties, preparations and reactions.
10) Heterocycles. Nomenclature of the main heterocycles. Aromatic and non-aromatic heterocycles. Purine and pyrimidine.
11) Stereochemical aspects. Definition of chiral objects and molecules. Enantiomers and racemic mixtures. Polarized light and polarimeter, the symbols (+) and (-). Determination of the absolute configuration and priority rules. Representation of chiral molecules according to Fischer. Meso-compounds and diastereomers.

ORGANIC MACROMOLECULES AND THEIR PROPERTIES
1) Amino acids and peptides: classification, structure and nomenclature of amino acids. Optical and acid-basic properties of amino acids. Peptide bond. Proteins: primary, secondary, tertiary and quaternary structures. Protein classification based on composition and biological function. Physico-chemical properties of proteins: optical and acid-base properties, solubility, denaturation. Peptides of biological interest.
2) Enzymes: classification, enzymatic catalysis, enzymatic kinetics. Michaelis-Menten equation.
3) Vitamins and coenzymes.
4) Carbohydrates: structure, classification. Mono- di- and, poly-saccharides.
5) Lipids: properties, structure and classification of saturated and unsaturated fatty acids, terpenes, soaps.
6) Nucleosides and nucleotides: structure and properties.

Didactic methods

80 Hours of classroom lectures (10 credits), with slides projection, divided as follows:
24 Hours of lessons concerning basic principles of General Chemistry and introduction to Organic Chemistry. Teacher: Anna Fantinati.
40 Hours of lessons concerning the study of the main classes of organic compounds. Teacher: Paolo Marchetti.
16 Hours of lessons concerning the study of organic macromolecules. Teacher: Giancarlo Fantin.

Learning assessment procedures

The exam aims to verify the knowledge of the training targets described above. The exam will be in written form with a duration of at least 45 minutes for each student and will be divided into 32 questions: for each correct answer 1 point will be assigned, for each answer not given 0 points will be assigned, for each wrong answer a penalty will be assigned of -0.2 points. Those who score 31 or 32 points will also be awarded the “lode”.

Reference texts

1) A copy of the slides used by the teacher during the lessons.
2) Introduction to Organic Chemistry
William H. Brown – T. Poon
5th Edition
EdiSES