PRINCIPI DI CHIMICA ORGANICA

At the end of the course, the students will know the fundamental principles of organic chemistry, their synthesis methods and the mechanisms through which organic compounds are formed and transformed. In particular, they will acquire the main notions of chemism of functional groups and stereochemistry.

The course is organized into frontal lessons. Exercises will also be performed (6 credits).

If the course is conducted in a mixed or distance mode, the necessary variations may be introduced in order to comply with the planned programme.

Information for students with disabilities and/or DSA

To guarantee equal opportunities and in compliance with Italian law (170/2010), interested students can ask for an interview with the teacher (before the beginning of the course or at least 30 days before the exam) in order to plan any compensatory and/or dispensative measures, without changing the learning objectives.

You can also contact the contact teacher CInAP (Centre for Active and Participatory Integration - Services for Disabilities and/or DSA) of our Department, Prof.ssa Teresa Musumeci.

Knowledge of basic concept of General Chemistry

1.      Covalent bonds in organic molecules

2.      Alkanes

Introduction to alkanes - Cycloalkanes - IUPAC and common nomenclature of alkanes and cycloalkanes - Physical properties - Conformations of acyclic alkanes - Introduction to cycloalkanes - Cyclohexane - Substituted cycloalkanes - Oxidation of alkanes.

3.      Isomers: the arrangement of atoms in space.

Cis-trans isomers - Chiral molecules - Stereogenic centers - Stereogenic centers in cyclic molecules - Representation of stereogenic centers with R or S descriptors - Diastereomers - Meso compounds - R or S assignments in compounds with two or more stereogenic centers - Disubstituted cycloalkanes - Physic Properties of stereoisomers - Chemical properties of enantiomers.

4.      Alkenes

Introduction - Nomenclature - Physical properties - Hydrohalogenation: electrophilic addition of HX - Markovnikov's rule - Stereochemistry of electrophilic addition of HX - Hydration: Electrophilic addition of water and alcohol - Halogenation: addition of halogens to alkenes - Stereochemistry of 'halogenation - Formation of halohydrins - Addition of borane to alkenes: hydroboration - oxidation - Oxymercuriation - Demercuriation - Reduction of alkenes.

5.      Mechanisms of organic reactions

Types of organic reactions - Bond breaking and formation - Bond dissociation energy - Thermodynamics - Enthalpy and entropy - Energy diagrams - Kinetics.

6.      Alkynes

Introduction - Nomenclature - Physical properties - Introduction to alkynes reactions - Addition of halogen acids - Addition of water - Reactions of acetylide anions - Reduction of alkynes.

7.      Alkyl halides and substitution reactions

Introduction to alkyl halides - Nomenclature - Physical properties - Polar carbon-halogen bond - General characteristics of nucleophilic substitution - Leaving group - Nucleophilic - Possible mechanisms for nucleophilic substitution - SN2 mechanism - SN1 mechanism - Stability of carbocations – Differences between SN2 and SN1 reactions.

8.      Alkyl halides and elimination reactions

General characteristics of elimination - Alkenes: the products of elimination reactions - Mechanism of elimination - Mechanism E2 - Zaitsev's rule - Mechanism E1 - Differences between E1 and E2 - Differences between SN1, SN2, E1 or E2.

9.      Alcohols, ethers and epoxides

Introduction - Structure and bonds - Nomenclature - Physical properties - Preparation of alcohols, ethers and epoxides - General characteristics: Reactions of alcohols, ethers and epoxides - Dehydration of alcohols to alkenes - Conversion of alcohols to alkyl halides with HX - Conversion of alcohols to halides SOCl₂ and PBr₃ alkyls - Oxidation of alcohols -  Reactions of ethers with strong acids - Reactions of epoxides in acidic and neutral conditions - Epoxidation.

10.   Radical reactions

Introduction - General characteristics of radical reactions - Halogenation of alkanes - Mechanism of halogenation - Differences between chlorination and bromination - Free radical addition to double bonds.

11.   Conjugation, resonance and dienes

Resonance and allyl carbocations - Common examples of resonance - Resonance hybrid - Electron delocalization, hybridization and geometry - Conjugated dienes - Carbon-carbon bond length in 1,3-butadiene - Electrophilic addition: 1,2 and 1,4 addition - Products obtained under kinetic or thermodynamic control.

12.   Benzene and aromatic compounds

Structure of benzene - Nomenclature of benzene derivatives - Stability of benzene - Aromatic, antiaromatic and non-aromatic compounds - Criteria for aromaticity: Hückel's rule - Aromatic ions - Aromatic heterocyclic compounds - Aromatic polycyclic hydrocarbons - Fused heterocyclic compounds - Examples of aromatic compounds.

13.   Reactivity of aromatic compounds

Electrophilic aromatic substitution - General mechanism - Halogenation - Nitration and sulfonation - Friedel-Crafts alkylation and acylation - Alkylation of benzene by acylation-reduction - Comparison between alkylation and acylation - Nomenclature of disubstituted and polysubstituted benzenes - Effect of substituents on reactivity: activating and deactivating agents - Effect of multiple substituents on orientation - Reactions of phenol.

14.   Aldehydes and ketones

Introduction - Nomenclature - Preparation of aldehydes and ketones - General reactivity of carbonyl compounds - Reactions of aldehydes and ketones: nucleophilic addition reactions - Nucleophilic hydride ion addition (reduction reactions) – Oxidation reactions - Reactions of carbonyl compounds with carbon nucleophiles: reactions with organometallic reagents, addition of cyanide ions - Reactions with nitrogen nucleophiles: addition of amines 1a and 2a - Reactions with oxygen nucleophiles: addition of water (hydration), addition of alcohols (formation of acetals, cyclic hemiacetals, introduction to carbohydrates) -  α, β-unsaturated carbonyl compounds: reactivity.

15.   Carboxyl compounds: carboxylic acids and derivatives

Structure and nomenclature - Preparation of carboxylic acids - Reactions of carboxylic acids: general characteristics - Carboxylic acids: strong Brønsted and Lowry acids - Derivatives of carboxylic acids - Structure and binding of carboxylic acid derivatives - Nomenclature of carboxylic acid derivatives - Reduction of carboxylic acids and their derivatives - Nucleophilic acyl substitution reactions - Reactions of organometallic reagents with derivatives of carboxylic acids - Reactions of acyl halides - Reactions of anhydrides - Reactions of carboxylic acids - Reactions of esters - Reactions of amides - Reactions of nitriles.

16.   Carbonyl and carboxylic compounds: condensation reactions in α

Introduction - Enols - Enolates - Carbon halogenation in α - Direct alkylation of enolates - Synthesis with the malonic ester - Synthesis with the acetacetic ester - Aldol reaction - Cross aldol reactions - Claisen reaction - Michael.

17.   Amines

Introduction - Structure and bonds - Nomenclature - Preparation of amines - Amines which react as bases - Relative basicity of amines and other compounds - Amines which react as nucleophiles - Reactions with nitrous acid: diazotation, N- nitrosamines - Substitution reactions of arildiazonium salts: substitution of the diazonium group with hydroxide, chloride, bromide, iodide and cyanide (Sandmeyer reactions), fluoride (Schiemann reaction) and with hydrogen.

18.   Carbohydrates

Introduction - Monosaccharides - The ᴅ-aldose family - The ᴅ-ketosis family - Cyclic forms of monosaccharides - Glycosides - Reactions of the OH groups of monosaccharides - Reactions of the carbonyl group: oxidation and reduction - Glucose is the most stable of aldohexoses - Reducing and non-reducing sugars - Disaccharides - Polysaccharides.

19.    Amino acids and proteins

Amino acids - Configuration of amino acids - Acid-basic properties of amino acids - The isoelectric point - Methods of synthesis of amino acids - Strategies of peptide synthesis.

1. Elementi di Chimica Organica – P. Y. Bruice – 2a Ed. 2017 – EdiSES, ISBN 978-88-795-9935-1 (contiene un kit di modellini molecolari)

2. Introduzione alla Chimica Organica – W. H. Brown – Ed. VI/2020 – EdiSES, ISBN  9788836230020

Test and/or oral interview