Introduction to the study of Organic Chemistry: atomic structure; electron configurations; chemical bonding nature; polar covalent bond; electronegativity and dipole moment. ● van der Waals and London forces ● hydrogen bonding ● formal charges and resonance; rules for resonance forms ● hybridization of carbon: sp3; sp2 and sp orbitals ● hybridization of oxygen and nitrogen ● acids and bases: the Brønsted-Lowry definition; acid and base strength; predicting acid-base reactions from pKa values; the Lewis definition; organic acids and organic bases ● electrophiles and nucleophiles in organic chemistry. Alkanes and Cycloalkanes: structures and properties ● common and IUPAC nomenclatures ● conformations of ethane ● conformation and stability of cycloalkanes ● cis and trans isomerism ● mechanism of the radical reaction: addition of halogens ● energy diagrams and transition states ● hybridation and stability of the radical intermediate ● hyperconiugation ● reactivity vs selectivity: Cl2 vs Br2. Alkenes: structures and properties ● cis and trans isomerism in alkenes ● nomenclature and sequence rules: the E, Z designation ● electrophilic addition of HX: the Markovnikov's rule; carbocation structure, stability and rearrangements ● addition of halogens: halohydrin formation ● addition of water ● oxymercuration and hydroboration ● addition of carbenes ● hydrogenation and oxidation reactions ● hydroxylation and cleavage ● addition of HBr in the presence of peroxides ● polymerization ● Diels-Alder cycloaddiction. Alkynes: structures and properties ● nomenclature ● preparation ● electrophilic addition of HX and halogens ● hydration ● reduction and oxidative cleavage ● alkyne acidity: formation of acetylide anions and alkylation of acetylide anions. Stereochemistry: chirality and optical activity ● tetrahedral carbon and enantiomers ● specific rotation ● physical properties of enantiomers ● sequence rules for specification of configuration ● diastereomers ● meso compounds ● racemic mixtures and their resolution ● Fischer projections ● chirality in Nature. Alkyl Halides: structures and properties ● nomenclature ● preparation ● Grignard reagents ● nucleophilic substitutions and eliminations ● stereochemistry and kinetics of the SN2 and SN1 ● stereochemistry and kinetics of the E2 and E1 ● the Zaitsev's rule. Alcohols: structures and properties ● nomenclature ● preparation ● acidity and basicity ● oxidation reaction. Ethers, Epoxides, Thiols and Sulfides: structures and properties ● nomenclature ● preparation ● acidity and basicity ● the Williamson synthesis ● ring-opening reactions of epoxides ● crown ethers and phase-transfer catalysts in organic reactions. Benzene and Aromaticity: structures and properties ● nomenclature ● molecular orbital description of benzene ● aromaticity ● the Hückel rule ● electrophilic aromatic substitution ● halogenation; the Friedel-Crafts alkylation; acylation; nitration and sulphonation of aromatic rings ● substituent effects ● nucleophilic aromatic substitutions ● pyridine and pyrroles ● acidity and basicity of phenols ● the Kolbe reaction and the synthesis of acetylsalicylic acid ● polycyclic aromatic compounds. Heterocycles Compounds: structures ● nomenclature ● five-membered unsaturated heterocycles: pyrrole, furan, and thiophene ● electrophilic substitution reactions ● six-membered heterocycle: pyridine ● basicity and electrophilic substitution of pyridine ● N-oxide pyridine formation ● nucleophilic substitution of pyridine. Aldehydes and Ketones: structures and properties ● nomenclature ● preparation ● nucleophilic addition reactions: relative reactivity of aldehydes and ketones; addition of H2O; HCN; Grignard reagents; hydride; amines and alcohols ● the Wolff-Kishner reaction ● the Clemmensen reaction ● the Wittig reaction ● the Cannizzaro reaction ● the keto-enolic tautomerism ● conjugate nucleophilic addition to alpha, beta-unsaturated aldehydes. Carboxylic Acids: structures and properties ● nomenclature ● preparation ● dissociation of carboxylic acids ● substituent effects on acidity ● carboxylic acid derivatives ● nucleophilic acyl substitution reactions ● chemistry of acid halides; acid anhydrides; esters; amides; nitriles ● the Claisen condensation reaction● the Stork reaction ● Fischer esterification reaction ● esters saponification: surfactants and supramolecular aggregation ● malonic esther synthesis ● acetoacetica esther synthesis. Amines: structures and properties ● nomenclature ● preparation ● acidity and basicity ● chirality of tertiary amines ● reactions of amines and arylamines ● diazonium salts and Sandmayer reaction ● tetraalkylammonium salts as phase-transfer catalysts in organic reactions ● the Gabriel synthesis ● the Hoffmann transposition ● the Hoffmann elimination. Carbohydrates: structures and properties ● nomenclature ● classification ● configurations of monosaccharides ● Fischer projections ● D and L series of the aldoses ● the Killiani-Fischer synthesis of monosaccharides ● cyclic structures of monosaccharides: hemiacetal formation and anomers ● mutarotation ● isomerisation reaction ● reduction and oxidation reactions of monosaccharides ● glycosides formation ● structures of disaccharides and polysaccharides in Nature. Amino Acids: structures and properties ● nomenclature ● classification ● acidity and basicity ● isoelectric point calculation ● the Strecker synthesis of alpha-amino acids ● resolution of R, S amino acids ● the sulphur bonding ● structure of peptides and proteins. Organic Compounds in Nature: biomolecules ● lipids and phospholipids ● fats and oils ● chemistry and properties of ascorbic acid. Nucleic Acids: structures and composition of DNA and RNA ● the Watson-Crick model.