Course content

Basic organic chemical concepts, such as chemical structures and nomenclature, physical properties, stereochemistry and relationship between structure and reactivity will be presented. Reaction mechanisms will be presented to give insight in chemical transformations. Alkanes and cycloalkanes: Conformations and cis-trans stereoisomers. Stereochemistry: Geometric isomers, conformation isomers, configuration isomers and pro-chirality. Absolute and relative configuration, R/S notational system for chiral C-atoms, optical activity (specific rotation), enantiomers, diastereomers, meso compounds, three-dimensional projections of molecule´s atoms, stereochemistry in chemical reactions. Alcohols and alkyl halides: Substitution (SN1/SN2), elimination (E1/E2), potential energy diagrams for multiple step reactions, carbocations and rearrangements. Nucleophilic substitution (SN2): Nucleophilic reagents, nucleophilicity versus basicity, solvent effects, leaving group, functionalization and stereochemistry. Structure and preparation of alkenes: Elimination reactions. Addition reactions of alkenes: (i) Hydrogenation, (ii) electrophilic addition of hydrogen halides (Markovnikov's rule and mechanism), (iii) acid-catalyzed hydration, (iv) hydroboration-oxidation to alcohols (anti-Markovinkov), (v) epoxidation. Alkynes: Preparation, acid-base properties, alkylation of terminal alkynes. Addition reactions of alkynes. Radical reactions: (i) radical intermediates, (ii) radical halogenation of alkanes, allylic and benzylic compounds. Alcohols: Preparation by (i) reduction of carbonyl compounds, (ii) ring opening of epoxides, (iii) dihydroxylation of alkenes. Reactions of alcohols: (i) Preparation of ethers, (ii) preparation of esters and (iii) oxidation to aldehyde/carboxylic acid/ketone. Grignard reagents and organolitium (organometallic compounds): Preparation, reactivity and reactions (base and addition to carbonyl compounds). Conjugation in alkadienes and allylic systems, allylic carbocations, resonance (electron delocalization), stability, isolated dienes, conjugated dienes, cumulated dienes. Conjugated dienes: (i) Preparation, (ii) addition of hydrogen halide, The Diels-Alder reaction. Arenes and aromaticity. Reactions of arenes: Electrophilic aromatic substitution. Radical halogenation of alkylbenzenes. Aldehydes and ketones: (i) Structure and reactivity, (ii) The Wittig reaction, (iii) preparation of imine, (iv) acetal formation, (v) enols and enolates, (vi) alkylation of enolates, (vii) aldol condensation. Carboxylic acids: (i) Acidity, (ii) preparation and (iii) reactions (ester formation). Carboxylic acid derivatives: (i) Esters, (ii) acid anhydrides, (iii) acid halides. Hydrolysis of carboxylic acid derivatives.

Sustainability in the preparation of organic compounds will be demonstrated in the lectures applying  "Green chemical" principles. Examples may include: (i) atom economy and efficiency, (ii) use of less hazardous and toxic chemicals, (iii) innocuous solvents and auxiliaries, (iv) preferred use of renewable raw materials, (v) shorter syntheses (avoid derivatization), (vi) catalytic rather than stoichiometric reagents, (vii) design products to undergo degradation in the environment.

Learning outcome

After completing this course the student will, in relation to the content of the subject: - be able to understand and communicate nomenclature and structure of organic chemical compounds - know basic principles for reactions in organic chemistry - be able to account for and derive mechanistic features of the reactions - be able to predict competing reactions - be able to name central reactions - have a basic knowledge of how functional groups affect electron density, properties and reactivity in organic compounds - be able to estimate pKa values for carboxylic acids, amines, alcohols and ketones in the presence of different functional groups. Through the course, the student will gain awarness regarding the importance of choosing sustainable solutions and possible challenges related to organic synthetic chemistry.

Learning methods and activities

The course consists of lectures (4 hours per week) and theoretical excercises (2 hours per week, 67% of exercises must be accepted).

Compulsory assignments

• Approved exercises

Recommended previous knowledge

The course is based on KJ1000.

Required previous knowledge

The course is based on KJ1000.

Course materials

Solomoms, Fryhle, Snyder "Organic chemistry", 12 ed.