KE518: Advanced organic synthesis

Comment

The course is co-read with: the corresponding master course KE814
If you plan to attend both Heterocyclic chemistry (KE553/KE835) and Advanced organic synthesis (KE518/KE814) in your complete study program, we recommend that you first attend KE553/KE835 or that you attend the two courses simultaneously.
The course is primarily offered in the second half of the spring semester

Entry requirements

The course cannot be followed by students who have followed and passed KE814.

Academic preconditions

Students taking the course are expected to: Have good knowledge of systematic organic chemistry corresponding to KE505 Organic chemistry.

Course introduction

The aim of the course is to give the student a broad overview over reactions in organic chemistry and enable the student to design synthetic routes to given target molecules, which is important in regard to projects and/or careers within for example medicinal chemistry, material sciences and chemical production.

The participants will acquire broad knowledge to modern organic chemical reactions and their mechanisms and be able to design synthetic routes to complex target molecules such as drugs and natural products.

The course builds on the knowledge acquired in the course KE505 Organic chemistry. It is also recommended that the material in KE553/KE835 Heterocyclic chemistry is known. The course gives an academic basis for bachelor and master projects that involve synthesis, for example within medicinal chemistry or materials science.

In relation to the competence profile of the degree it is the explicit focus of the course to:

Give the competence to plan synthesis projects.
Give skills to design and plan synthetic routes to given target compounds.
Give knowledge and understanding of organic chemical reactions and their theoretical basis and mechanisms.

Expected learning outcome

The learning objective of the course is that the student demonstrates the ability to:

Perform a retrosynthetic analysis of the structure of a given target molecule, e.g. a natural product or a pharmaceutical compound.
Design a synthetic route to the target molecule on basis of the retrosynthetic analysis.
Explain retrosynthetic terms (e.g. disconnection, functional group interconversion, synthon) and strategies (e.g. convergent vs. linear synthesis)
Explain the purpose of protecting groups, give examples of protecting groups for functional groups like alcohols, amines, carboxylic acids, aldehydes and ketones, give conditions for their introductions and removal, and use them in design of synthetic routes.
Demonstrate through understanding of the covered reactions as well as the basic reactions covered in the required basic organic chemistry course, including:
Suggest reasonable reaction conditions for given transformations
Predict the outcome of a given reaction
Propose a reasonable reaction mechanism

The covered reaction types include:

Oxidations
Reductions
Substitution-, addition- and elimination reactions
Alkylation of enolates and enamines (e.g. the aldol reaction)
Pericyclic reactions (cycloadditions, sigmatropic and elektrocyclic reactions)
Palladium catalyzed coupling reactions
Olefin metathesis

Give mechanisms for the mentioned reactions

Explain chemoselectivity, regioselectivity and stereoselectivity (including diastereo- and enantioselectivity), and relate this to the covered reactions.

Content

The following main topics are contained in the course:

Retrosynthesis and retrosynthetic analysis
Organic chemical reactions
The theoretical basis and mechanisms for the reactions

Literature

Clayden, Greeves and Warren: Organic Chemistry, 2nd edition, Oxford University Press, 2012.

Scientific articles and notes..
See Itslearning for syllabus lists and additional literature references.

Examination regulations

Exam element a)

Timing

June

Tests

Oral exam

EKA

N530023102

Assessment

Second examiner: External

Grading

7-point grading scale

Identification

Student Identification Card

Language

Normally, the same as teaching language

Duration

1 hour preparation and 30 minutes examination

Examination aids

Allowed, a closer description of the exam rules will be posted in itslearning

ECTS value

Indicative number of lessons

42 hours per semester

Teaching Method

These teaching activities are reflected in an estimated allocation of the workload of an average student as follows:

Intro phase (lectures) - 28 hours
Training phase: 14 hours

The teaching takes place as lectures where both slides and blackboard are used and with questions and problems distributed throughout the lectures. The students will work with problems at home that will be presented in the excercise classes. Towards the end of the course there will be focus on reterosynthesis and design of synthetic routes where the methods and reactions discussed previously will be used.

Activities during the study phase:

Study of the textbook and lecture slides
Solve problems that will be presented in the examination classes

Teacher responsible

Name	E-mail	Department
Steffen Bähring	sbahring@sdu.dk	Institut for Fysik, Kemi og Farmaci

Timetable

Odense

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Administrative Unit

Fysik, kemi og Farmaci

Team at Educational Law & Registration

NAT

Offered in

Odense

Recommended course of study

Profile	Education	Semester	Offer period

Transition rules

Transitional arrangements describe how a course replaces another course when changes are made to the course of study.

If a transitional arrangement has been made for a course, it will be stated in the list.

See transitional arrangements for all courses at the Faculty of Science.