Organic Chemistry (Intermediate Course)

Timetable

Module aim (aims)

The main aim of the lecture (15h) is to bring organic chemistry to students in clear and the most interesting way possible, and to present organic chemistry as an exciting, important science which is instrumental to biology but also to daily life.

Emphasis will be on understanding the relationship between structure and reactivity of organic molecules, on substitution and elimination reactions, and on chemistry of the carbonyl group.

 

The main objectives of the discussion sessions (30h) are to show students how to apply what they have learned to a new setting, reasoning a way to a solution rather than memorizing a multitude of facts.

The sessions will be focused on solving problems concerning organic reaction mechanisms and stereochemistry,

Pre-requisites in terms of knowledge, skills and social competences (where relevant)

Basic knowledge of organic and general chemistry.

Syllabus

Week 1: Introduction (fundamental topics)

Chemical bonds, electronegativity, type of arrows, resonance, acids and bases, nucleophiles and electrophiles, functional groups.

Week 2: Addition reactions

Structure and reactivity of alkenes. Electrophilic addition to alkenes - general mechanism, hydrohalogenation, hydration, halogenation, free-radical addition to alkenes.

Week 3: Nucleophilic addition

Structure and reactivity of carbonyl compounds, addition to carbonyl group.

Week 4: Nucleophilic substitution

Structure and reactivity of alkyl halides. Substitution of alkyl halides: S_N2 mechanism, S_N1 mechanism. S_N1 or S_N2 mechanism?

Week 5: Elimination reactions

Elimination of alkyl halides: E2 mechanism, E1 mechanism. E1 or E2 mechanism? S_N1, S_N2, E1 or E2 Mechanism?

Week 6: Structure and reactivity of aromatic compounds

General mechanism of electrophilic aromatic substitution (halogenation, nitration, sulphonation, Friedel-Crafts alkylation, Friedel-Crafts acylation), effect of substituents on electrophilic aromatic substitution, orientation effects in substituted benzenes.

Nucleophilic aromatic substitution (addition-elimination mechanism, benzyne mechanism)

Week 7: Structure and reactivity of aromatic compounds

Nucleophilic aromatic substitution (addition-elimination mechanism, benzyne mechanism)

Week 8: Condensation of enols and enolate ions

Acidity of C=O compounds (enolate formation), halogenation, intramolecular and crossed aldol condensations, Claisen and Dieckmann condensations, alkylation of enolate ions, alkylation and acylation of enamines,  hard and soft nucleophiles; charge vs. orbital control, kinetic (1,2) vs. thermodynamic (1,4) addition, the Michael reaction, Robinson annulation.

Reading list

1. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry.
2. Gorzynski Smith, Organic Chemistry
3. G. Wade, Organic Chemistry
4. McMurry Organic Chemistry