Elements of Chemistry (2016/2017)

Course code
4S003712
Credits
12
Coordinator
Fabio Piccinelli
Teaching is organised as follows:
Unit Credits Academic sector Period Academic staff
ELEMENTI DI CHIMICA GENERALE 6 CHIM/03-GENERAL AND INORGANIC CHEMISTRY I sem. Fabio Piccinelli
ELEMENTI DI CHIMICA ORGANICA 6 CHIM/06-ORGANIC CHEMISTRY II sem. Mariapina D'Onofrio

Learning outcomes

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MM: ELEMENTI DI CHIMICA GENERALE
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The aim of the course is to acquire the main concepts of General Chemistry and some notions of Inorganic Chemistry. At the end of the course the student must be able to solve problems regarding the General Chemistry, showing good reasoning skills and ability in the connection of different concepts. The course also aims to give to the student adequate means in order to deal with other courses, such as Organic Chemistry, Biochemistry, etc... In particular, the course is preparatory to the Organic Chemistry course.
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MM: ELEMENTI DI CHIMICA ORGANICA
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The course presents the conceptual bases to provide the student with the basics of organic chemistry. Knowledge of organic compounds and their reactivity is the basis for dealing with advanced topics for the comprehension of biological and biomolecular phenomena. At the end of the course, the student will have to demonstrate the ability to deal with the structures and the chemical properties and typical reactions of the organic molecules and must be able to apply such knowledge to describe the reaction mechanisms. The basic concepts learned during the course will provide students with the tools of molecular interpretation of the organization of biological systems.

Syllabus

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MM: ELEMENTI DI CHIMICA GENERALE
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Introduction. Chemical and physical properties of matter and their measurements. Elements, atoms and compounds. Nomenclature of inorganic compounds. Types of chemical reactions. Reaction stoichiometry. Ideal and real gases. Thermochemistry. Internal energy and enthalpy. Standard enthalpy of reaction and formation. Atomic structure. Atomic orbitals. Electronic configuration, Aufbau principle. Periodic properties: atomic and ionic radii, ionization energy, electron affinity, electronegativity. Elementary notions on the ionic bond. Ionic compounds. Covalent bond. Lewis formula. Resonance. Molecular geometry and polarity. Orbital hybridisation. Single and multiple bonds. Interparticle forces. Properties of liquids. Solutions. Binary liquid mixtures. Distillation. Properties of solids. Chemical kinetics. Arrhenius equation. Reaction mechanisms. Chemical equilibrium. Equilibrium constant. Acid-base equilibrium. Acid, base and salt solutions. Acid-base titration. Buffer solutions. Solubility equilibrium. Entropy. Spontaneous processes. Gibbs free energy. Standard free energy of reaction and formation. Electrochemical cells. Electrolysis. The course is made of 48 h of lectures Suggested textbook: N. J. Tro Chimica-un approccio molecolare EdiSES (available also in the ebook version)
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MM: ELEMENTI DI CHIMICA ORGANICA
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- Bond angles and carbon hybridisations, polarity of the molecules in relation to the electronegativity of the atoms of the molecule, the concept of resonance and different ways of representing the bonds, representation of the electron displacement in a reaction. - Acids and bases in organic chemistry: definitions according to Bronsted / Lowry and Lewis, how to predict the strength of an acid and the equilibrium position in an acid-base reaction, the relationship between molecular structure and acidity (resonance and relocation of the charge, inductive effect and electronegativity). - Saturated hydrocarbons: alkanes and cycloalkanes, nomenclature and structure, mention of combustion reaction and radical substitution, constitutional isomerism of alkanes, cis-trans isomers of cycloalcans, chair and boat conformations, equatorial and axial substitutions. - Unsaturated hydrocarbons: alkenes and alkynes, nomenclature, structure, characteristic reactions of alkenes: addition reactions and Markovnikov’s rule, regioselectivity, hydro-halogenation, hydration, halogenation, hydrogenation. - Chirality of the molecules: stereoisomers, enantiomers, diasteroisomers, optical activity and R / S configuration of a stereocentre, meso compounds and racemic mixtures, polarimeter and polarized light. - Alogenoalcans: nomenclature, structure, nucleophilic substitution and elimination reactions. Mechanisms SN1, SN2, E1, E2, stability of exiting groups, relative efficacy of nucleophiles, stability of carbocations, solvent effect, differences between intermediate and transition states, competition between nucleophilic substitution and elimination reactions, energy diagrams of a reaction. - Alcohols, phenols, ethers and thiols: structure, nomenclature and chemical properties, oxidation and dehydration reactions, secondary and tertiary primary alcohols, acidity comparisons. - Benzene and aromatic compounds: resonance and Huckel's rule, nomenclature and structure, aromatic molecules of biological interest. General overview of reactions (aromatic electrophilic substitution) - Aldehydes, ketones: nomenclature and structure, physical properties, reactivity, reduction and oxidation of aldehydes and ketones, nucleophilic addition, reaction with Grignard reagents, formation of emiacetals and acetals, formation of an immine from an aldehyde or ketone, keto–enol tautomerism, alpha-substitution reactions, acidity, condensation reactions. - Amine: nomenclature, basicity. - Carboxylic acids and derivatives: nomenclature, structure, properties and acidity, acyl nucleophilic substitution, Carboxylic acids derivatives reactivity, amide bond properties, thioester and acyl phosphate. - Carbohydrates: classification and configuration, mutarotation, reducing sugars, Fischer and Haworth projections, disaccharides and polysaccharides of biological interest. - Lipids: Classification and structure of fatty acids, phospholipids, prostaglandins, terpenoids and steroids. - Amino acids: structure, basic-acidity properties, isoelectric point determination, overview on the protein structural characteristics, polypeptide bond, secondary structure. - Nucleic Acids: DNA RNA, nucleosides and nucleotides, overview on DNA transcription and translation. - Software for bi and three-dimensional visualization of the structures of organic molecules, molecular representation systems. - Codes for molecules representation used in databases.

Assessment methods and criteria

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MM: ELEMENTI DI CHIMICA GENERALE
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The final examination consists of a written part (multiple choice test). The student will solve 30 questions regarding the whole programme: 1 point for each right answer, -0.2 for each wrong answer and 0 point for each missing or canceled answer. The final mark will be expressed in thirtieths. All students reaching the mark of 17 have the right to do an oral part, with the aim to obtain the final mark of 18. These rules apply for attending students as well as non attending ones.
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MM: ELEMENTI DI CHIMICA ORGANICA
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Written exam: 6 exercises, available time 1 and a half hours. The obtained grade will be averaged with the one obtained in the module of "General Chemistry Elements" The exam consists of a written verification of the level of knowledge acquired on organic chemistry. The student should be able to correctly represent the molecules using the conventions in use, recognize isomers, identify reactive groups, and describe in detail the reaction mechanisms. It is moreover verified the knowledge of molecule codes used in databases. The test consists of a written exam divided into six open-ended exercises (time available 90 minutes). The final grade is given by the sum of the scores obtained in the individual exercises. If the outcome of the written exam is ≥ 16/30 it is possible to scheduled the oral exam.

Reference books
Author Title Publisher Year ISBN Note
N. J. Tro Chimica-un approccio molecolare EdiSES 2012
W. H. Brown- T. Poon Introduzione alla Chimica Organica, IV° edizione (Edizione 4) EdiSES 2014
McMurry Chimica organica PICCIN  
Bruice Elementi di chimica organica (Edizione 2) EdiSES 2017 9788879599276
L. G. Wade Jr. Fondamenti di Chimica Organica PICCIN 2014 978-88-299-2300-7
J. G. Smith Fondamenti di chimica organica, 3/e (Edizione 3) McGraw Hill 2018
Brown Poon Introduzione alla chimica organica (Edizione 5) EdiSES 2014 9788879598255