ORGANIC CHEMISTRY 2: FUNDAMENTALS
- Overview
- Assessment methods
- Learning objectives
- Contents
- Full programme
- Teaching methods
- Contacts/Info
A deep knowledge of the topics tackled during the courses of General Chemistry and Organic Chemistry 1 is an essential prerequisite.
The final examination consists in a two-step procedure with written and oral tests. The former is usually structured in exercises on
- reactivity and synthesis;
- structure identification and separation of mixture of organic compounds.
During the oral test, students will be examined on all the topics tackled during the lessons.
The final mark will take into account the evaluation of part B of the course, based on the reports of the experimental activities.
The course aims at increasing students’ knowledge of organic chemistry by these topics:
- nitrogen-containing functional groups: structure, conversion and reactivity;
- aromatic compounds: structure, reactivity, and synthesis.
At the end of the course, students will be able:
1) to knowledge properties and reactivity of aromatic and heteroaromatic systems, also taking into account possible functional groups;
2) to identify the reactivity of molecules in different conditions depending on their structures;
3) to plan a multi-step synthesis of aromatic molecules starting from assigned starting materials;
4) to operate in safety in a laboratory of organic chemistry;
5) to apply the most important procedures of synthesis and techniques of purification for organic compounds.
Amines and their derivatives (12 hours).
Amines nomenclature, structure and physical properties. Amines basicity and acidity. Stereochemical aspects. Ammonium quaternary salts and amine N-oxides. Phase transfer catalysis (PTC). Reactions of alkylation, reductive amination, acylation and sulfonylation. Formation of imines and enamines, Mannich reaction. Diazotation reaction. Synthesis of aliphatic amines.
Amides: nomenclature, properties, acidity. Reactivity towards acids, bases and reducing agents. Beckmann transposition.
Amino acids, peptides and proteins: amino acids and peptides nomenclature. Stereochemistry of -amino acids. Amino acids and peptides acid-base properties. -amino acids synthesis and resolution. Peptides synthesis: protective groups, amidation reactions. Peptides and proteins hydrolysis. Proteins primary and secondary structure.
Aromaticity (6 hours)
Historical background. Inductive, mesomeric, steric and hyperconjugative effects. Aromaticity according to Hückel. Examples of aromatic, antiaromatic and non-aromatic compounds. Hammond postulate. Thermodynamic and kinetic control. Electrophilic aromatic substitutions (EASs) mechanism. Positional isomerism in substituted benzenes. Activating and deactivating groups (vs. EASs). Substituent-governed regioselectivity.
Reactivity of aromatic compounds (10 hours)
EASs classification. Formation of C(arom)-N, C(arom)-S, C(arom)-halogen and C(arom)-C bonds. Metalloaryl mediated EASs (hints).
Aromatic compounds classes (38 hours)
Alkylbenzenes and alkenylbenzenes: nomenclature, main properties, reactivity at the aromatic system. Benzylic halogenation (Wohl Ziegler), benzylic hydroperoxidation, lateral chains oxidation, Birch semireduction. Alcohols and benzylic halides: nomenclature, main properties, reactivity. Synthesis methods.
Aromatic aldehydes and ketones: nomenclature, main properties. Reactivity towards oxygen-, sulphur-, nitrogen-or carbon-based nucleophiles. EASs. Reduction and oxidation. Synthesis methods.
Aromatic carboxylic acids: nomenclature, main properties. Carboxylic acids acidity. Nucleophilic acyl substitution and electrophilic aromatic substitution reactions. Esterification and reduction. Synthesis methods.
Aromatic acyl chlorides: nomenclature, main properties. Reactivity towards nucleophiles.
Aromatic esters and anhydrides: nomenclature, main properties. Acidic and basic hydrolysis. Reduction with hydrides. Transesterification. Reactivity towards nucleophiles. EASs. Synthesis methods.
Aromatic amides: nomenclature, main properties. Acidity. Acidic and basic hydrolysis. Reduction. Reactivity towards nucleophiles. EASs. Synthesis methods.
Aromatic nitriles: nomenclature, main properties. Acidic and basic hydrolysis. Reduction. Reactivity towards nucleophiles. EASs. Synthesis methods.
Arylic halogenides: nomenclature, main properties. Nucleophilic aromatic substitution reactions and reactions mediated by transition metals. EASs. Synthesis methods.
Nitroarenes: main properties. EASs. Synthesis methods.
Aromatic amines: nomenclature, main properties. EASs. Reactivity towards electrophiles and oxidation reactions. Synthesis methods.
Diazonium salts: main properties and reactivity.
Phenols: nomenclature, main properties. Acidity. Reactivity towards electrophiles. Transpositions and electrophilic aromatic substitution reactions. Oxidation. Synthesis methods.
Quinones: nomenclature, main properties. Redox equilibria. Reactivity towards dienes and nucleophiles. Synthesis methods.
Polycyclic hydrocarbons: reactivity and synthesis.
Heteroaromatic compounds (6 hours)
Heteroaromatic systems: monohetero penta-atomic compounds. Halopyridines and pyridine N-oxides. Benzocondensed heterocycles. Azoles and diazines.
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The teaching activities are supplied by classroom lecturing supported by.PPT slides and by laboratory activities.
Professor is available to meet the students any day by previous appointment.