66992 - Organic Chemistry (M-Z)

Learning outcomes

After completing the course, the student will have the knowledge necessary to the understanding and use of the main organic compounds in the level of classification, structure and properties. The student also acquires the main concepts useful for the interpretation of the reactivity of organic compounds. Finally, through simple experiments of preparation and isolation of organic compounds, the student completes and builds their knowledge of basic organic chemistry, also useful to the understanding of biological compounds.

Course contents

1. Electronic structure and hybridization of the carbon atom. Covalent bonds in organic molecules; electronic resonance. Polarity and electronegativity. Nucleophiles and electrophiles.
2. Functional groups. Description and recognition of the main functional groups: alkanes, alkenes, alkynes, arenes, alcohols, halides, aldehydes, ketones, phenols, thiols, amines, carboxylic acids, esters, amides, anhydrides, acyl halides. The IUPAC system of nomenclature.
3. Alkanes and cycloalkanes. Nomenclature. Concept of isomerism and empirical formula. Structural formula. Structure and conformations of alkanes. Ring strain and conformations of cycloalkanes.
4. Stereochemistry. Definitions. Chirality. Stereogenic. Assignment of the absolute configuration: diastereoisomers. meso compounds. Compounds with two stereocenters. Fischer projections. Brief survey on chirality in biology.
5. Alkyl halides. Structure, properties and nomenclature. Preparation: radical alogenation of alkanes. Nucleophilic substitution, S_N1, S_N2, stereochemistry of S_N; elimination reaction E1 and E2.
6. Alcohols, phenols and ethers: Nomenclature. Physical Properties. Reaction of alcohols. Reactions of oxidation and reduction. Epoxides synthesis and reaction. Reactions of epoxides. Thiols.
7. Alkenes and Alkynes. Structure, properties and nomenclature. Isomers of C=C bond. Electrophilic addition to C=C double bond, addition of alogenhydric acids, water, hydrogen. Structure and stability of carbocations. Addition of oxygen (epoxides). Conjugated diene. Acids and bases. Alkynes. Nomenclature, structure and acidity of alkynes. Reaction acetylide anion. Reaction with various electrophiles.
8. Aromatic Compounds. Aromatic hydrocarbons. Resonance. The Hückel rule. Electrophilic aromatic substitution. Halogenation of benzene. Alkylation reaction according to Friedel-Crafts. Halogenation, nitration, and sulfonation of benzene. Reactivity of aromatic compounds in the aromatic substitution reactions. Effect of substituents: activating or deactivating group.
9. Carbonyl compounds. Structure and reactivity of the carbonyl group. Reaction of nucleophilic attack on the carbonyl compounds. Reactions of addition of alcohols, HCN, amines, Grignard reagents. Attack hydride ions. Reduction with NaBH₄. Oxidation of carbonyl group.
10. Carboxylic acids and derivatives: nomenclature. Structure of carboxylic acids. Acidity. Reaction Nucleophilic acyl. Reaction of carboxylic acids. Hydrolyisis of esters.
11. Keto-enol tautomery. Reactivity of enols. Formations of enolates. Reactivity of enolates. Aldol condensation. Aldol condensation cross.
12. Amines: nomenclature, structure and reactivity. Reactions of amines. Alkaloids: notes .
13. Natural products, carbohydrates, structure, stereochemistry, nomenclature of monosaccarids; di- and polysaccarides: lipids, fatty acids and triglicerids, surfactants and detergents; aminoacids, structure and stereochemistry, proteinogenic aminoacids; peptidic bond, polypeptides and proteins.
14. Exercises about all topics above mentioned.
15. Practical laboratory training

Readings/Bibliography

Brown, Iverson, Ansylyn, Foote - Chimica Organica - EdiSES

P.Y. Bruice – Chimica Organica - EdiSES

J. McMurry - Fondamenti di Chimica Organica - Zanichelli

Smith – Fondamenti di Chimica Organica – McGraw Hill

Teaching methods

Lessons and discussion.

Classroom exercises.

Practical laboratory training.

Assessment methods

Written and oral exam on the theoretical and laboratory program carried out.

Teaching tools

PowerPoint video projection

Organic chemistry laboratory and instruments for practical training

Office hours

See the website of Paola Franchi