ORGANIC CHEMISTRY
Academic year and teacher
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- Versione italiana
- Academic year
- 2022/2023
- Teacher
- CARMELA DE RISI
- Credits
- 9
- Didactic period
- Secondo Semestre
- SSD
- CHIM/06
Training objectives
- Knowing
The student will learn basic knowledges with respect to:
- structure and physical-chemical properties of the most important classes of carbon compounds;
- the fundamental organic reactions and their mechanisms.
Skills
The student will acquire the ability to:
- identify the most important classes of carbon compounds and their physical-chemical properties;
- define the fundamental organic reactions and their mechanisms;
- apply the known knowledges to understand all chemical aspects related to pharmaceutical and health products. Prerequisites
- To take the final examination (learning assessment procedures), students must have passed the exam of General and Inorganic Chemistry.
Course programme
- - Structure and bonding: chemical bonding, Lewis structures, isomerism, resonance, shape of molecules, hybridization, electronegativity, polarity of bonds and molecules (11 hours)
- Organic molecules and functional groups: representation of organic structures, functional groups, intermolecular forces, physical properties of molecules, intermolecular forces in biological systems (9 hours)
- The three-dimensional structure of molecules: conformations, stereoisomers, chirality, stereogenic centers, R or S configuration, enantiomers, diastereoisomers, meso compounds, Fischer projections, physical and chemical properties of stereoisomers (12 hours)
- Functional groups and reactivity: reactive sites, prediction of reactivity, the equations of organic reactions, types of organic reactions, reaction mechanisms, arrow formalism, catalysts (2 hours)
- Acid-base reactions: Brønsted-Lowry acids/bases, Lewis acids/bases, nucleophiles and electrophiles, relative basicity (nucleophilicity) of organic bases (amines and other nitrogen compounds) (6 hours)
- Nucleophilic aliphatic substitution: general features, leaving group, nucleophile, possible mechanisms, stereochemical aspects, alkyl halide reactions (intermolecular processes with oxygen and nitrogen nucleophiles - formation of alcohols, ethers, esters, ammonium salts; intramolecular processes - synthesis of epoxides), reactions of alcohols and ethers (transformation into alkyl halides with strong acids, epoxide ring-opening with strong nucleophiles) (4 hours)
- Nucleophilic acyl substitution: general mechanism, relative reactivity of carboxylic acid derivatives, reactions of carboxylic acids, some specific reactions (synthesis of amides and esters from acyl chlorides and anhydrides, Fischer esterification, ester hydrolysis), application of nucleophilic acyl substitution to natural molecules (soap synthesis, soap structure and action, basic concepts on the structure/water solubility relationship for organic molecules) (5 hours)
- Electrophilic aromatic substitution: benzene and aromatic compounds, criteria for aromaticity, general mechanism of electrophilic aromatic substitution, specific reactions (Friedel-Crafts acylation, nitration, sulfonation) (2 hours)
- The elimination reaction: general characteristics, possible mechanisms, elimination of alkyl halides (dehydrohalogenation), Zaitsev's rule, competition between substitution and elimination, elimination reactions of alcohols (dehydration) with strong acids (2 hours)
- Nucleophilic addition: general mechanism, addition of charged nucleophiles (hydride ion - carbonyl reduction) and neutral nucleophiles (alcohols - synthesis of hemiacetals and acetals, amines - synthesis of imines and enamines) (5 hours)
- Electrophilic addition: general characteristics, Markovnikov’s rule, specific reactions (hydrohalogenation of alkenes, hydration of alkenes and alkynes) (2 hours)
- Oxidation and reduction: general principles, basic concepts on i) reduction of aldehydes, ketones, derivatives of carboxylic acids, alkenes and alkynes, ii) oxidation of alcohols, aldehydes and alkenes (2 hours)
- Reactions at the a carbon of carbonyl compounds: enols, keto-enol tautomerism, enolates and their general reactivity, specific reactions (Claisen reaction, aldol condensation, Michael reaction) (4 hours)
- The nomenclature of organic molecules: principles of chemical nomenclature, systematic and common nomenclature, nomenclature of the main classes of organic molecules (6 hours) Didactic methods
- The course is delivered through theoretical lessons aimed at exposing and explaining the contents of the program, integrated with exercises
Learning assessment procedures
- The learning assessment is determined by a final test, which permits to evaluate the student's acquisition level of the training objectives.
The exam is ORAL and generally consists of four/five questions on topics covered in the course. The candidate will not be asked to "repeat" the concepts, but to write on the blackboard (like one would do to solve a typical organic chemistry exercise).
The topics under examination will be selected in order to verify not only the degree of knowledge and understanding acquired, but also the ability to communicate, connect and / or compare different aspects covered during the course.
The duration of the interview will be approximately 35 minutes, but may possibly vary according to its progress.
The exam will be considered as passed with a minimum score of 18 out of 30 with honors. Reference texts
- a) Text adopted:
- Janice Gorzynski Smith, Fondamenti di Chimica Organica (4/ed), McGraw-Hill
b) For further consultation:
- W.H. Brown, M.K. Campbell, S.O. Farrell, Elementi di Chimica Organica (2/ed), EdiSES
- William H. Brown, Thomas Poon, Introduzione alla Chimica Organica (6/ed), EdiSES
- Felix S. Lee, Guida alla soluzione dei problemi da Introduzione alla Chimica Organica di W.H. Brown, T. Poon (5/ed), EdiSES
