ORGANIC CHEMISTRY
Academic year and teacher
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- Versione italiana
- Academic year
- 2016/2017
- 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, resonance, acids and bases, organic molecules and functional groups, intermolecular forces, functional groups and reactivity. (15 hours) Acyclic alkanes and cycloalkanes: structure and nomenclature. Conformations of acyclic alkanes, cyclohexane and substituted cyclohexanes. Cis-trans isomerism of disubstituted cycloalkanes. (7 hours) Stereochemistry: chiral and achiral molecules, stereogenic centres, R and S chirality descriptors, diastereomers, meso compounds, optical activity, racemic mixtures. (7 hours) Alkyl halides and nucleophilic substitution reaction: structure and nomenclature of alkyl halides, the nucleophilic substitution reaction. SN2 and SN1 mechanisms, effects determining the mechanism. Stability of carbocation intermediates. Nucleophilic substitution reaction as a tool for the synthesis of alcohols, ethers and epoxides. Structure and nomenclature of alcohols and ethers. Substitution reactions of alcohols, ethers and epoxides. (10 hours) Alkyl halides and elimination reactions: E2 and E1 mechanisms, effects determining the mechanism. The products of elimination reactions: alkenes. Structural characteristics and nomenclature of alkenes, cis-trans or E/Z isomerism, stability of alkenes and Zaitsev rule. Synthesis of alkynes by elimination reactions of dihaloalkanes. Essential features and nomenclature of alkynes. Acidity of terminal alkynes and SN2 substitution reaction of acetylide anions. Elimination reaction of alcohols in acidic medium. (4 hours) Electrophilic addition reactions of alkenes and alkynes: Markovnikov rule. Hydroalogenation, hydration, halogenation of alkenes and alkynes. Preparation of halohydrins. (3 hours) Conjugated dienes, electrophilic 1,2- and 1,4- addition reactions. (1 hour) Benzene and aromatic compounds: benzene structure, criteria for aromaticity. Examples of aromatic compounds. (1 hour) Electrophilic substitution reaction: general mechanism. Halogenation, nitration, sulfonation, Friedel-Crafts acylation and alkylation reactions. Electrophilic substitution reaction of monosubstituted arenes.(5 hours) Carboxylic acids and its derivatives: structure and nomenclature. Reactivity of carboxylic acids as strong acids, relative acidity of carboxylic acids, phenols and alcohols. Acidity of aliphatic carboxylic acids. Sulfonic acids. (2 hours) Acylic nucleophilic substitution: general mechanism and relative reactivity of carboxylic acids and its derivatives. Reaction of acyl halides and acid anhydrides. Fischer esterification. Acid or base catalyzed hydrolysis of esters and amides. Nitriles: synthesis, hydrolysis. (7 hours) Aldehydes and ketones, and nucleophilic addition reaction: structure and nomenclature of aldehydes and ketones, general mechanism nucleophilic addition. Grignard reagents: structure and behaviour either as bases or nucleophiles. Nucleophilic addition of Grignard reagents, cyanide ions, amines, and alcohols. Preparation of cyclic emiacetals and cyclic acetals. Alfa,beta-unsaturated carbonyl compounds: 1,2- and 1,4-conjugate addition. The Michael reaction. (6 hours) Reactivity of carbonyl compounds at the alfa-carbon: enolates, enols and keto-enol tautomerism. Alkylation of enolates, aldol condensation reaction and Claisen reaction. (2 hours) Oxidation and reduction reactions: hydrogenation of alkenes and alkynes, reduction of carbonyl compounds and nitriles. Oxidation of alcohols. Epoxidation and syn-dihydroxylation of alkenes. Oxidative cleavage of alkenes and alkynes. (1 hour) Amines: structure, classification, nomenclature and chemical behaviour both as bases and nucleophiles. Factors affecting amine basicity: inductive, resonance, aromaticity and ibridation effects. (1 hour)
Didactic methods
- The course consists of classroom front lessons
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 final test goes through a written examination (duration: 3 h) followed by an oral examination, which takes place in a later day.
The oral examination day is communicated during the written examination. Importantly, just the use of calculating machines and periodic table is permitted during the written examination, while no study notes and/or books can be referred to.
The written test consists of 10 questions regarding all of the topics covered in the course. Each question is worth 3 points (score 3 for a fully correct answer, a lower score for a partially correct answer). A minimum score of 18/30 is required to pass the written examination and take the oral test.
The oral test (duration: 20-30 min) will take the cue from the topics faced in the written examination and will help the teacher to give a precise student’s judgement. If the oral examination result is judged to be insufficient, the student must repeat the written examination in one of the following exam periods. Reference texts
- William H. Brown - Thomas Poon, Introduzione alla Chimica Organica (4 ed.), EdiSES
Felix S. Lee, Guida alla soluzione dei problemi da Introduzione alla Chimica Organica di William Brown e Thomas Poon (4 ed.), EdiSES
Janice Gorzynski Smith, Fondamenti di Chimica Organica (2/ed), McGraw-Hill
