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, i(v) hydroboration-oxidation to alcohols (anti-Markovinkov), (v) epoxidation. Alkynes: Preparation, acid-base properties, alkylation of terminal alkynes. Addition reactions of alkynes. 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. Interpretation of simple proton NMR spectra.

Relevance for sustainability in chemistry. The 12 principles of green chemistry must be known to the candidate. Examples of sustainable and "Green" production of chemicals will be given: (i) use of environmental friendly and non-toxic reagents and solvents, (ii) use of renewable resources (iii) energy efficient synthesis routes (iv) catalysed reactions compared to stoichiometric reactions, (v) design of degradable chemicals.

Learning outcome

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

Learning methods and activities

TKJ4102 is the theoretical course in basic organic chemistry for students enrolled in the Ms. Tech. program. TKJ4102 consists of lectures and exercises. 67% of the exercises must be approved in order to attend teh final exam. The exercises are approved by answering tehm directly in the WileyPLUS digital learning platform or by attending the exercise supervisions. Exercise 7 and exercise 11 are compulsory to attend/answer. These two exercises are approved as exercises if 50% of the tasks (points) are correct.

Compulsory assignments

• Exercises

Recommended previous knowledge

A prerequisite is to have passed courses equivalent to TMT4115 General Chemistry 1/TMT4110 General Chemistry

Course materials

e-Book and digital learning material WileyPLUS: Solomons, Fryhle, Snyder: "Organic chemistry", 13th ed. Wiley, 2023.

Credit reductions