Synthetic Organic Chemistry

6 EC

Semester 2, period 4

5254SYOC6Y

Owner Master Chemistry (joint degree)
Coordinator dr. Tati Fernández Ibáñez
Part of Master Chemistry (joint degree), track Molecular Sciences, year 1

Course manual 2017/2018

Course content

Retrosynthetic analysis; formation of carbon-carbon bonds via ionic, radical and pericyclic mechanisms; rearrangement and fragmentation; heterocyclic chemistry; stereochemistry and asymmetric synthesis.

Study materials

Literature

  • J. Clayden, N. Greeves, S. Warren and P. Wothers, 'Organic Chemistry', 2nd Edition, Oxford University Press, 2012.

Objectives

Intended Learning Outcomes (ILOS) The students

  • are able to identify the type of transformation required to obtain a target organic molecule.
  • are able to define the reaction conditions for different types of organic transformations.
  • can explain the mechanism of the organic reactions explained during the course as well as similar transformations not covered during the course.
  • can apply the organic reactions covered during the course in the synthesis/retrosynthesis of more complex organic molecules.
  • are able to identify different type of organic transformations based on the stereochemistry of the final product.
  • are able to identify different type of organic transformations based on the reaction conditions.
  • are able to design synthetic routes for the synthesis of complex organic molecules.
  • are able to compare different synthetic routes.
  • are able to present research articles correctly, clearly and in a comprehensive manner to a broad audience.
  • show curiosity and interest to solve problems when encountering synthetic challenges.
  • at the end of the course are confident to propose a synthetic route.

Teaching methods

  • Lecture
  • Presentation/symposium
  • Self-study
  • Supervision/feedback meeting

Lectures, total synthesis presentations by the students and problem solving sessions.

Learning activities

Activity

Number of hours

Hoorcollege

26

Presentatie

22

Tentamen

3

Vragenuur

2

Werkcollege

26

Zelfstudie

89

Attendance

The programme does not have requirements concerning attendance (OER-B).

Additional requirements for this course:

All students must attend the total synthesis presentations. Exceptions are only possible after personal agreement between student and supervisor.

Assessment

Item and weight Details

Final grade

80%

Tentamen

20%

Presentation

1%

Tentamen

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

 

lectures Mon 9-11 h and Wed 9-11 h, from Feb 6 to March 22, 2017 (but not on March 8)

tutorials Mostly Mon 15-17 h and Wed 15-17 h, from Feb 6 to March 22 (not on March 8), in two groups, A and B.

total synthesis Mon and Wed 11-13 h and/or 13-15 h, from Feb 13 to March 22 (not on March 8).

The total synthesis presentations are obligatory for everyone wishing to pass the SOC course (both presentation and presence at presentations by colleagues). Details will be provided separately.

final questions Tuesday March 28, 13-15 h, F1.02 (treatment of a previous exam)

exam written exam (open book) Thursday March 30, 2017, 13-16 h, JWS, room 2

Books and notes may be consulted during the exam.

 

 

Date Lecturer Onderwerpen Studiestof
Mon Feb 6 HH Retrosynthetic analysis Ch 28
Wed Feb 8 TF Aromatic heterocycles 1: reactions Ch 29
Mon Feb 13 HH Sulfur, silicon and phosphorus Ch 27
Wed Feb 15 TF Aromatic heterocycles 2: synthesis Ch 30
Mon Feb 20 TF Saturated heterocycles Ch 31
Wed Feb 22 HH Stereoselectivity in cyclic molecules Ch 32
Mon Feb 27 HH Diastereoselectivity  Ch 33
Wed March 1 TF Cycloadditions Ch 34
Mon March 6 HH Rearrangement and fragmentation Ch 36
Mon March 13 HH Radical Reactions Ch 37
Wed March 15 TF Sigmatropic and electrocyclic reactions Ch 35
Mon March 20 TF Carbenes Ch 38
Wed March 22 HH Asymmetric synthesis Ch 41

Timetable

The schedule for this course is published on DataNose.

Additional information

Rough-and-ready knowledge of J.P. Clayden, N. Greeves, and S. Warren Organic Chemistry, chapters 1-26;

Further details on the total synthesis presentations

All students wishing to pass the Synthetic Organic Synthesis course must give an oral presentation on the total synthesis of an interesting compound, published in the (recent) literature. The presentation should take about 15 minutes and the audience consists of the other students and the teachers (Hiemstra, Fernandez, Van Maarseveen and/or Ingemann).

The total number of students is divided over two groups, A and B. Please check datanose to find out to which group you belong. The schedule of presentations (student name, compound name, publication, date and time) will be provided as soon as possible and can be found on the Blackboard site.

Please note that you are not permitted to do the written exam if you have not presented a total synthesis yet.

All students will receive the name of one target compound, the literature reference where the synthesis is described and the date and time they have to give the presentation. They must prepare a Powerpoint presentation (maximum of 12 sheets, ChemDraw ACS settings), which describes the details of the total synthesis in an attractive way (clear structures and drawings, some colour!).

The presentation must include the following items:

  • Relevance of the target molecule, its biological source or activity 
  • Authors and university (or company), where the research was carried out
  • Retrosynthesis and synthetic strategy • Synthesis in detail, starting from commercially available chemicals
  • Most attention for key steps (mechanism)
  • Pertinent stereochemical issues (racemic or enantiopure, etc.)
  • Overall yield, number of steps, efficiency

The teachers will give a mark for the presentation, which will count as 20% of the final mark of the whole course. The teachers thus should receive both a digital and a paper copy of the presentation. All presentations will be put on the Blackboard site.

 

Contact information

Coordinator

  • dr. Tati Fernández Ibáñez