60/56/60/1 - ORGANIC CHEMISTRY WITH PRACTICE
Academic Year 2015/2016
Free text for the University
COSTANTINO FLORIS (Tit.)
- Teaching style
- Lingua Insegnamento
|[60/56] INDUSTRIAL BIOTECHNOLOGY||[60/56-00 - Ord. 2014] PERCORSO COMUNE||10||100|
Knoweledge: proper use of the organica chemistry language, to write and read formulae of the organic compounds, to know the main functional groups and their reactivity, to correlate the chemical structure to the physical properties.
Competence: ability to understand an organic chemistry reaction, apply the main stereochemical projections, distil solvents, extract and isolate natural substances, recognize UV-Vis spectra and gaschromatograms, use simple laboratory instrument, carry out thin layer chromatographies, polarimetric analyses and concentration and dilution calculations, write a suitable and concise report.
Behaviour: the course stimulates both the personal learning and the group work
It is advisable that the students have a basic knowledge of mathematics and physics and have passed the General Chemistry examination
Dissociation energy and bond and molecule polarity. Structure and physical properties. Intra and intermolecular forces. Solubility. Acids and bases. Isomerism. Bond forces and reaction heat. Activation energy. Reaction velocity. Transition state and reactivity.
Hydrocarbons. Alkanes, Cycloalkanes, Alkenes, Alkynes, Dienes, Aromatics
Physical properties. Structure. Nomenclature. Alkyl groups.
Alkanes: Halogenation and mechanism. Alkyl radicals.
Alkenes: Double bond C_C. Cis-trans isomerism. Carbocations. Hydrogenation. Electrophilic addition. Mechanism and reactivity. Dienes: Conjugated, unconjugated and cumulated dienes. Resonance in conjugated dienes. 1,2- and 1,4-addition.
Aromatic hydrocarbons: Benzene structure and resonance. Aromatic ring. Hydrogenation and combustion heat. Electrophilic aromatic substitution. Mechanism. Nitration, sulfonation, halogenation, alkylation. Reactivity and orientation theory.
Tetrahedral carbon atom. Polarized light and optical activity. Enantiomerism. Chirality and chiral centres. Fischer projection.
T Physical properties. Structure. Nomenclature. Aliphatic nucleophilic substitution. Nucleophiles and leaving groups. SN1 and SN2 substitutions: mechanism and kinetics. Elimination reactions: orientation and reactivity.
Aryl halides: Ring electrophilic substitution.
Alcohols, Phenols, Ethers, Epoxydes
Physical properties. Structure. Nomenclature. Hydrogen bond.
Alcohols: Dehydration. Reactions with hydrohalic acids. Oxidation.
Phenols: Acidity and salts. Ring substitutions. Coupling.
Ethers: Cleavage with acids. Basic character. Electrophilic substitution in aromatic ethers.
Epoxides: Acid and basic cleavage.
Glycols and polyols. Sulfur compounds. Thiols, thioethers, sulfonic acids.
Aldehydes and ketones
Physical properties. Structure. Nomenclature. Reactions. Nucleophilic addition to the carbonyl group. Oxidation and reduction. Addition of water, cyanide, ammonia derivatives, alcohols. Alpha,beta-unsaturated compounds. Reactivity
Carboxylic acids, functional derivatives of acids
Physical properties. Structure. Nomenclature.
Acids: Ionic dissociation and salts. Acidity. Carboxylate anions.
Functional derivatives: Reduction. Nucleophilic acyl substitution. Alkaline and acid hydrolysis.
Proteins: Amide bond, resonance and structure
Oils and fats, soap and surfactants. Structure and physical properties. Saturated and unsaturated fatty acids.
D and L configuration. Stereoisomers. Oxidation and reduction reactions. Reducing sugars. Osazones. Cyclic structure. Glycosides. Monosaccharides, disaccharides, polysaccharides
Acidity of alpha hydrogens. Aldol and Claisen condensation.
Amines, heterocyclic compounds
Physical properties. Structure. Nomenclature.
Amines: Salts and quaternary ammonium salts. Basicity. Amide formation. Aromatic amine basicity and ring substitution. Diazonium salts.
Heterocyclics: Pyrrole, furan, thiophene, pyridine. Reduction
Laboratory activity concerns the following subjects
Polarity, physical properties and melting point
Purification of organic compounds
Separation by distillation
Specific rotation of sugars
Extraction and characterisation of caffeine
Solvent extraction of essential oils
Thin layer chromatography of vegetal pigments
Aniline and phenol identification and wool dyeing
10 CFU are attributed to the Organic Chemistry course for 98 hours of activity. The activity is divided in 6 CFU of lectures, corresponding to 48 hours, and in 4 CFU of laboratory activity, corresponding again to 48 hours. The course lasts about 12 weeks.
Three time a semester the students are assessed by means of intermediate written tests on the program developed up to that moment.
Previous intermediate and final test are at students’ disposal.
Verification of learning
A written test and, if necessary, an oral test.
The final grade depends on different factors:
a) Knowledge of a scientific language pertaining to course subject;
b) Concepts possessed and ability to coherently connect them
c) Ability to use properly the chemical symbolism
d) Ability to communicate graphically the concepts by means of formulae, schemes, equations
As a consequence, the grades can be:
a) Sufficient (from 18/30 to 20/30)
The student has modest expression ability, elementary knowledge of the subject with many gaps, only rudimental conceptual connections, basic symbolic and graphic expression ability
b) Fair (from 21/30 to 23/30)
The student has fair expression ability, sufficient knowledge of the subject with some gaps, conceptual connections of moderate complexity, acceptable symbolic and graphic expression ability
c) Good (from 24/30 to 26/30)
The student has satisfactory expression ability, detailed knowledge of the subject with few gaps, adequate conceptual connections, average symbolic and graphic expression ability
d) Very good (from 27/30 to 29/30)
The student has full expression ability, deep knowledge of the subject with negligible gaps, ample conceptual connections, complete symbolic and graphic expression ability
e) Excellent (from 30/30 to 30/30 cum laude)
The student has outstanding expression ability, complete knowledge of the subject with negligible gaps, exceptional conceptual connections, superior symbolic and graphic expression ability
The student should be stimulated to different readings, in order to compare different exposures, so I suggest any recent text of Organic Chemistry for the University. In this respect, I propose the following texts:
-G.Smith- Fondamenti di Chimica Organica – McGraw-Hill Education
-J.McMurry – Fondamenti di Chimica Organica – Zanichelli
-P.Y.Bruice – Elementi di Chimica Organica - Edises
-W.H.Brown, T.Poon- Introduzione alla Chimica Organica- Edises
Before entering the laboratory students are educated about the risk factors