CHIMICA ORGANICA I E CHIMICA ORGANICA II

Academic Year 2018/2019 - 2° Year - Curriculum Tossicologia dell'Ambiente e degli Alimenti

Learning Objectives

• Organic Chemistry I

  The course focuses on the fundamental chemistry of carbon compounds and an appreciation of its relevance to biology and toxicology. Topics will include nomenclature, structure, properties, synthesis, and reactions, of the major functional groups of organic compounds.
  The fundamental objective is to stimulate the student to apply his reasoning skills in the study of matter, limiting the mnemonic effort to the learning of a restricted set of the basic principles of Organic Chemistry.

• Organic Chemistry II

  FRONTAL LESSONS

Course Structure

• Organic Chemistry I

  The lectures for this course will be a combination of classic blackboard lectures and PowerPoint.

Detailed Course Content

• Organic Chemistry I

  Introduction to Organic Chemistry:

  • Review of general chemistry: atoms, molecules, bonding, polar and nonpolar molecules, intermolecular forces, solubilities, Lewis structures, preliminary ideas of resonance, arrow formalism, acids and bases. Orbitals, molecular orbital description of bonding, hybridization and molecular geometry. Acids and bases revisited: Electronegativity, resonance structures, definitions and strengths of acids and bases, organic acids and bases.

  Alkanes

  • Properties, conformational analysis, structural isomerism and nomenclature, alkyl groups. Cycloalkanes and their naming, stability, ring strain, polycyclic molecules.

  Alkenes

  • Structure and reactivity; nomenclature, cis/trans, E/Z notation; hydrogenation, relative stabilities. Reactions to carbon-carbon double bonds (electrophilic addition reactions): mechanism of hydrogen halide additions, regiochemistry, resonance effects, carbocation stabilities, addition of other reagents (hydroboration, addition of halogens, and water, epoxidation and chemistry of oxiranes, oxymercuration, cyclopropanation, carbenes, ozonolysis), dimerization and polymerization of alkenes. Carbocation rearrangements, alkene reduction and oxidations (permanganate and osmium tetroxide). Industrial preparation. Cycloalkenes.

  Dienes

  • conjugation, introduction to the concept of aromaticity. Diene polymers, natural and synthetic rubber, conjugation, color, and the chemistry of vision.

  Alkynes

  • Structure and reactivity; bonding and nomenclature, relative stabilities, triple bonds in rings. Addition reactions of alkynes (hydrogenation, hydrogen halide additions, water addition). Preparations.

  Stereochemistry

  • cis-trans isomerism, conformations and Newman projections, chirality, isomers: enantiomers, R/S notation, diastereomers, optical activity; Cahn-Ingold-Prelog rules; meso compounds, epimers; Fischer proiections.

  Alkyl halides

  • Physical and chemical properties; preparations, momenclature; reactions: substitution reactions of alkyl halides - S_N2 and S_N1 mechanisms. Elimination reactions: E1 and E2 mechanisms; Zaitsev’s Rule.

  Alcohols

  • Properties: Acidity, Alkoxides; Naming alcohols: - Preparation;Grignard Addition Reactions: Synthesis from Formaldehyde, from an Aldehyde, from a ketone; Synthesis from an Ester; Synthesis from an Epoxide; from haloalkane; Organolithium Alternative. Reduction: Synthesis from an Aldehyde, from a Ketone, from an Ester, from a Carboxylic Acid. Reactions: Conversion to haloalkanes; Oxidation; Ether and alkene formation.

  Ethers, Epoxides, and Sulfides

  • Nomenclature of Ethers, Epoxides, and Sulfides; Structure and Bonding in Ethers and Epoxides; Physical Properties of Ethers; Preparation of Ethers: The Williamson Ether Synthesis. Reactions of Ethers: A Review and a Preview; Acid-Catalyzed Cleavage of Ethers. Epoxides: Preparation: Conversion of Vincinal Halohydrins to Epoxides; Reactions of Epoxides: Nucleophilic Ring-Opening Reactions of Epoxides; Acid-Catalyzed Ring-Opening Reactions of Epoxides. Sulfides; Preparation; Reactions: Oxidation of Sulfides: Sulfoxides and Sulfones; Alkylation of Sulfides: Sulfonium Salts.

  Dienes

  • Classes of Dienes; Relative Stabilities; Electron Delocalization in Conjugated Diene; Preparation. Reactions: Addition of Hydrogen Halides to Conjugated Dienes, Halogen Addition; allylic bromuration; The Diels-Alder Reaction, Stereoselectivity.

  Aromatic systems

  • Benzene, Physical Properties; Reactivity, Kekule's Formulation of the Benzene Structure; Structural Features of Benzene; Resonance Description of Bonding in Benzene; The Stability of Benzene; Substituted Derivatives of Benzene and Their Nomenclature; Polycyclic Aromatic Hydrocarbons. Reactions of Arenes: Mechanistic Principles of Electrophilic Aromatic Substitution. Nitration, Sulfonation, Halogenation, Friedel-Crafts Alkylation and Acylation; Synthesis of Alkylbenzenes by Acylation-Reduction. Rate and Orientation in Electrophilic Aromatic Substitution; Substituent Effects in Electrophilic Aromatic Substitution: Activating and Deactivating Substituents; Halogen Substituents; Multiple Substituent Effects; Preparation of Alkenylbenzenes; Addition Reactions of Alkenylbenzenes.
• Organic Chemistry II

  ALDEHYDES AND KETONES;CARBOXYLIC ACID, NITRILES AND CARBOXYLIC ACID DERIVATES; CARBONYL ALPHA-SUBSTITUTION REACTIONS; CARBONYL CONDENSATION REACTIONS; AMINES; HETEROCYCLES.BIOMOLECULES: CARBOHYDRATES; AMINO ACIDS,PEPTIDE AND PROTEINS;LIPIDS; NUCLEIC ACIDS.

Textbook Information

• Organic Chemistry I

  1. P. Y. Bruice: Organic Chemistry – EdiSES (molecular models included), III Ed/2017 – ISBN 9788879599351
  2. D. Klein: Fundamental Organic Chemistry – Pearson Italy, 2016 – ISBN 9788891900968
  3. J. G. Smith: Fundamental Organic Chemistry – McGraw-Hill, III Ed/2018 – ISBN 9788838694431

• Organic Chemistry II

  Fondamenti di Chimica Organica – L. G. Wade, Jr. – Piccin.

  • Chimica Organica – P. Y. Bruice – 2a Ed. EdiSES (include un kit di modelli molecolari).
  • Chimica Organica – a cura di B. Botta, AA. VV. – 2a Ed. Edi-Ermes.
  • Manuale Virtuale di Chimica Organica: http://organicavirtuale.altervista.org/VirtualText/intro1.html Guida Ragionata allo Svolgimento