CHEM 760/7600 - Heteroatoms in Organic Synthesis

Semester: Winter 2019

Professor: A. Schwan | Discipline: Organic | Campus: Guelph


The course is intended to provide students with an understanding of the utility and mechanism of heteroatom-based functionalities in organic synthesis.  The influence of the heteroatom will be emphasized with examples displaying how the heteroatom directs reactivity and where applicable, stereochemistry. Students will be required to deliver two seminars and write two research essays which, when totaled, will comprise a major component of their grade.

One 2 1/2 hour lecture per week, Thursday nights starting at 7:00 pm in the main link room. First lecture is Mon. Jan. 10, 2019. There will be no lecture on Feb. 7 or during reading week (Feb. 21).  The scheduled lectures will be composed of Schwan lecturing for 7 class periods and 3-4 class periods of student presentations.

Schwan lectures will introduce functional groups and their bonding and electronic charateriztics and also will survey the families of reactions applicable to the functional groups. Presentations by the student will provide a more in-depth assessment of particular reactions or groups of reactions based on the heteratom functional group.

Learning Objectives

-to recognize and understand the role of key heteroatom containing functional groups in organic synthesis
-to communicate synthetic and mechanistic chemistry brought about by heteroatom containing functional groups
-to compile and summarize a finite aspect of synethic chemistry
-to increase the student’s synthetic chemistry knowledge by unveiling new and valuable  functional groups and reactivity modes
-to grow a students mechanistic skills by broadening their exposure to a wider selection of chemistries and reactive intermediates
-to develop an understanding of the role of uncommon bonding effects in organic chemistry
-assist in the development of skills for critical assessment of scientific information


Please understand that an audit is an official entry on your transcript and there are certain course requirements to achieve this. Audit does not mean “sitting-in”. Professor Schwan generally does not recommend the audit or ‘sitting in’ process, since

  1. your graduate career will be assessed primarily by the quality of your thesis and
  2. a graduate degree means that you can learn things for yourself. It follows that your time should be spent on your research project.


Conventional sources of references:

Library including online books
Google Scholar
Web of Knowledge

Unconventional sources of references:
Science of Synthesis is available on Guelph campus (at least):


The course grade will be based on two oral seminars, two research essays and a final exam The final examination will be given in April.

The final grade will be calculated as follows:                                                           

            research seminar 1             15%     `                     on Feb. 14 or 28
            research essay 1                  20%                            due Mar. 7
            research seminar 2              20%                            on Mar. 28 or Apr. 4
            research essay 2                  25%                            due Apr. 11                                 
            final examination                 20%                            suggested to be Apr. 18

Presentations and research essays are expected to contain mechanism components, synthetic examples, selectivity features, local (geographic) connections of contributions, and demonstration of heteroatom properties to observed chemistry. Essays are expected to mirror the presentation. See additional documentation for further instructions and guidance.

Main heteroatoms to be addressed: sulfur, selenium, silicon, phosphorus, boron

Anticipated Marking Scheme (with consideration to guidelines and expectations noted above):
Slides                                                                                     6
Oral Presentation and Clarity                                            6
Quality and Frequency of Questions Asked                    3
Scientific Content                                                                15        /30
English                                              5
Typos/Syntax                                    5
Reference Compilation                   5
Scientific Content                            15        /30


Seminar and Essay Guidelines

General Content Components

Brief history (longer if there is an important evolution of the reaction)
Chemical methods to incorporate the heteroatom, if applicable.
Requirement of bondings feature unique to the heteroatom (“This reaction works because….” or “The stereochemical outcome is because……”)
Mechanism with modern references; any mechanism reinterpretations or contentious points?
Value in synthesis with examples:  important methodology; natural products or drugs or industrial application,  if possible
Any selectivity features of the reaction?
Any local contributions? (GWC2?, Ontario? Canada? Michigan or Upstate NY?)
Any sustainable aspects or conditions? (green achievements, atom economy, circumvent protecting groups?)
What other reactions effect similar chemistry, if any?
Have the reagents or conditions evolved over time?

Components as above plus :
Effective screen layout: Consistent appearance (all molecules the same size), your original graphics with no mistakes, effective atom size/bond length ratio; innocuous reaction arrows; balance of text and atom size to molecule size; 4 to 8 molecules per slide
Good speech
10-12 minutes in length
Questions from others: At least 1 question for every two presentations
Written report:

Components as above plus :
Good flow; good, mature English; proper use of articles; self consistent reference structure and syntax; proper journal abbreviations – use JOC format
Absolutely no plagiarism. Text will be compared to www using “Turnitin”.
No tables of R groups/conditions/yields. Use a reference manager.
15-20 double spaced pages including diagrams but not including references. Submitted as Word file (easier to provide feedback) or as pdf.
The slides you employ for your presentation are to be distributed to the class (via Schwan) before evening presentation.
Also, presenters are expected to provide a 1 page mechanistic and synthetic summary to other classmates as a study summary for the final exam.
Timing Advice and due dates:
Week 1: claim a topic, find too many references and start learning the material
Week 2: Choose references for inclusion; start drawing molecules; start planning structure of seminar and essay.
Week 3: Bring the seminar to a point of near completion, while adding fragmented points and thoughts to your essay;
Week 4: do substantial writing of essay
Week 5; no lecture, complete seminar and send tentative presentation to Schwan for feedback
Week 6 or Week 7, (Feb. 14 or Feb. 28): present Seminar 1
Reading week:  new topic decided
Week 8 (March 7) Essay 1 due
Week 11 or Week 12, (Mar. 28 or Apr. 4): present Seminar 2
April 11: Essay 2 due.
April 18, final exam.


  • Thu: 7:00 pm - 9:20 pm in MacN 101/EIT 2053

Office Hours

Office: MacN 336, Guelph Campus. 824-4120 X58781; E-mail: [email protected] FAX: 1-519-766-1499