Organic Chemistry

Course manual 2023/2024

Course content

In the first year you have learned the several types of hybridization of atoms in organic molecules and how this affects the spatial orientation of the atoms but also the electronics, both inductively and via conjugation. Besides stereochemistry, the properties and reactivities of functional groups were treated. Finally, basic reactions such as nucleophilic additions/substitutions and elimination reactions were discussed in a mechanistic way showing the flow of electrons using curly arrows.

The theoretical part (4 EC) carries on after the first year course using ‘Clayden’. A lab course (2 EC) completes the course learning the preparation of useful molecules via modern multistep procedures.

During class, a series of new reactions will be treated mainly to make C-C bonds. The focus will be on understanding the mechanisms. Topics will be addtions to alkenes and electrophilic aromatic substitution, conjugatie additions and reactions of enols and enolates such as alsol and Claisen reactions. Furthermore, chemo- and regio-, and (dia)stereoselectivity will be discussed and protective group strategies. The course will end by demonstrating that also nature relies on the reactions and mechanisms that have been taught in the organic chemistry courses so far.

Objectives

• The student is able to draw the tautomeric structures of organic molecules and predict their relative stabilities based on steric and electronic parameters.
• The student is able to discriminate different reaction types of α,β-unsaturated carbonyl compounds and other electron-poor alkenes with hard and soft nucleophiles (direct vs. conjugate addition) and is able to deduce the reaction products.
• The student is able to discriminate between the different mechanisms of aromatic substitution reactions (electrophilic or nucleophilic) and apply these reactions to the synthesis of new molecules.
• The student is able to categorize the reactivity of enolate anions in the formation of C-C bonds in substitution and addition reactions and apply these reactions to the synthesis of new molecules;
• The student is able to explain the chemo-, regio-, and (dia)stereoselectivity of reactions and to apply protective groups in the synthesis of new molecules.
• The student is able to describe the mechanisms of various biosynthetic pathways with a special focus on cofactors.
• The student is able to give examples of the use of renewable starting materials.
• The student is able to carry out the practice of synthesis using modern methods such as photochemistry, electrochemistry, flow chemistry.

Teaching methods

• Hoorcollege
• Werkcollege
• (Computer)practicum

This course aims at improving and extending the knowledge of the underlying mechanisms of the key reactions in (bio)organic chemistry to enable the student to:

1. a) predict how several functional groups will react under a given set of conditions.
2. b) describe several types of key reactions by means of detailed mechanisms.
3. c) design a short multistep route to a functional organic molecule.

In the practical part you will learn the techniques that now form the frontline of organic synthesis (flow chemistry, electrochemistry and photochemistry) together with synthesis from renewable materials.

Learning activities

Attendance

Aanwezigheidseisen opleiding (OER-B):

• Van elke student wordt actieve deelname verwacht aan het onderdeel waarvoor hij staat ingeschreven.
• Als een student door overmacht niet aanwezig kan zijn bij een verplicht onderdeel van het onderdeel, dient hij dit zo snel mogelijk schriftelijk te melden bij de betreffende docent. De docent kan, eventueel na overleg met de studieadviseur, besluiten om de student een vervangende opdracht op te leggen.
• Het is niet toegestaan om verplichte onderdelen van een onderdeel te missen als er geen sprake is van overmacht.
• Bij kwalitatief of kwantitatief onvoldoende deelname, kan de examinator de student uitsluiten van verdere deelname aan het onderdeel of een gedeelte daarvan. Voorwaarden voor voldoende deelname worden van te voren vastgelegd in de studiewijzer en/of op Canvas.

Assessment

Fraud and plagiarism

The 'Regulations governing fraud and plagiarism for UvA students' applies to this course. This will be monitored carefully. Upon suspicion of fraud or plagiarism the Examinations Board of the programme will be informed. For the 'Regulations governing fraud and plagiarism for UvA students' see: www.student.uva.nl

Course structure

Timetable

The schedule for this course is published on DataNose.

Contact information

Coördinator

• prof. dr. J.H. van Maarseveen