90967 - Organic Chemistry

Learning outcomes

The course involves the study of the structure, properties, reactions, and preparation of organic compounds, which are sorted into organic families defined by their functional groups. At the end of the course, the student will understand the fundamental principles of organic chemistry, the main synthetic methods to obtain organic compounds, and the structure-reactivity relationship governing the behavior of organic molecules, with broader reference to medicinal chemistry and life science.

Course contents

Part 1 (Prof.ssa Claudia Tomasini)

1. Description of the main functional groups: alkanes, alkenes, alkynes, arenes, alcohols, phenols, ethers, amines, alkyl and aryl halides, aldehydes, ketones, carboxylic acids, esters, anhydrides, amides, acyl halides, thioesters, radicals.
2. Definition of acids and bases according to Brönsted and according to Lewis.
3. Alkanes and cycloalkanes: nomenclature, structural isomers, cis/trans isomers, decalin.
4. Stereochemistry: conformations of ethane and butane; tension and conformation of small rings; formations of cyclohexane and substituted cyclohexane; the decaline; definition of isomers and chirality; nomenclature (CIP system); acyclic and cyclic molecules with two or more stereocenters; meso compounds; optical activity; racemic mixtures.
5. Understanding Organic Reactions
6. Alkyl halides: nomenclature and structure. SN1 and SN2 substitution reactions and E1 and E2 elimination reactions: first-order and second-order mechanisms and kinetics and comparison between the various mechanisms.
7. Alkenes: structure, isomerism, nomenclature, cyclic alkenes. Reactions of alkenes: electrophilic addition of halogen acids, water, halogens. Carbocations. Markovnikov's rule. Stereochemistry of additions.
8. Alkynes: nomenclature, structure and acidity.

Part 2 (Prof. Luca Valgimigli)

1. Alcohols, Ethers, and Epoxides
2. Oxidation and Reduction 
3. Conjugation, Resonance
4. Benzene and Aromatic Compounds - electrophilic aromatic substitution
5. Carboxylic Acids and the Acidity of the O–H Bond
6. Introduction to Carbonyl Chemistry; Organometallic Reagents
7. Aldehydes and Ketones—Nucleophilic Addition
8. Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution

Part 3 (Dott.ssa Demetra Giuri)

1. Substitution Reactions of Carbonyl Compounds at the α Carbon. Formation of enolates. Alkylation reaction, malon ester synthesis and acetoacetic ester synthesis.
2. Carbonyl condensation reactions. Aldol reaction. Claisen condensation. Michael reaction.
3. Amines: nomenclature, classification and structure. Basicity of amines. Reactions of amines. Alkaloids.
4. Carbohydrates: general structure and classification. Representation by Fischer and Haworth projection. Definition of D series and L series. Cyclic structure and formation of hemiacetals. Reaction of monosaccharides. Disaccharides. Polysaccharides.
5. Amino acids and proteins: alpha-amino acid structure, isoelectric point. Peptides: structure, peptide bonding. Synthesis strategy of a peptide: peptide bond formation, role of protecting groups. Primary, secondary, tertiary and quaternary structure of proteins.
6. Lipids. General definition and classification: fatty acids, waxes, fats and oils, soaps. The hydrolyzable lipids: acylglycerols, phospholipids, sphingomyelins. Nonhydrolyzable lipids: prostaglandins, isoprene, steroids.

Readings/Bibliography

Organic Chemistry 6th Edition By Janice Smith

ISBN10: 1260119106
ISBN13: 9781260119107

McGraw Hill

Teaching methods

The topics listed in the program will be fully covered, with a particular attention to the reaction mechanisms.

Assessment methods

After each module students can take a partial exam on the subjects that each Professor presented during his/her lessons.

Students must pass all the partial exam.

If not, the preparation is tested by a written exam followed by an oral exam.

Teaching tools

Overhead projector, PC, blackboard

Office hours

See the website of Claudia Tomasini

See the website of Luca Valgimigli

See the website of Demetra Giuri