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  • Advances in Chemical Synthesis
    This Course Guide has been taken from the most recent presentation of the course. It would be useful for reference purposes but please note that there may be updates for the following presentation.

    CHEM S445
    Advances in Chemical Synthesis



    Introduction

    Welcome to CHEM S445 Advances in Chemical Synthesis.

    CHEM S445 is a five-credit, one-semester, elective course offered by the School of Science and Technology as part of the BSc Programme in the Bachelor of Science in Applied Science (Biology and Chemistry). It is designed for students with differing backgrounds -- i.e. you may be majoring in biology or chemistry -- who are pursuing an Honours Degree.
    This higher-level course builds on the foundation of organic chemistry provided by CHEM S345. You are advised to study CHEM S345 Principles of Chemical Synthesis or its equivalent before taking this course so that you will have an advantage in understanding the basic principles and concepts of synthetic organic chemistry. Here in CHEM S445 we will cover topics relevant to the strategy of organic synthesis, with particular emphasis on selectivity and synthetic design. You will be trained in developing independent abilities in academic analysis and presentation skills by conducting the various lab-based projects.

    CHEM S445 Advances in Chemical Synthesis covers a wide range of advanced information in organic chemistry, including reaction mechanisms, and strategies for synthetic methods and their applications to the synthesis of natural products and other aspects. This advanced course expands on introductory chemical topics including electrophilic addition, nucleophilic substitution and elimination reactions. In order to introduce you to modern synthetic strategies, CHEM S445 will cover selected journal articles and review papers that have received a great deal of attention in the current scientific world.

    The purpose of this course is to help you develop advanced knowledge of synthetic tools, and to learn how to apply these theoretical strategies to real examples. Finally, you will be able to propose reasonable synthetic schemes and mechanisms of various organic reactions, and you will be inspired to appreciate the art of advanced organic chemistry.

    What this course helps you do

    Achieving the successful synthesis of a complex target molecule is a satisfying activity for an organic chemist. This course explores the synthetic methods for target compounds. The aims and course learning outcomes are shown below:

    Course aims

    The course aims to:

    • Introduce you to advanced information in organic chemistry, starting from reaction mechanisms and strategies of synthetic methods, and then extending to their applications to the synthesis of natural products and other aspects.

    • Encourage you to think critically about the synthetic routes to some selected natural products as reported in journal articles and review papers.

    • Develop your ability to apply theoretical strategies related to synthetic tools to real examples of organic synthesis.

    • Motivate you to propose reasonable synthetic schemes and mechanisms for various organic reactions.

    • Inspire you to appreciate the art of advanced organic chemistry.

    Course learning outcomes

    On completion of the course, you should be able to:

    • Identify the properties of various functional groups in organic molecules.

    • Apply the reactive species in the chemical reactions.

    • Select reasonable retro-synthetic schemes for large target molecules.

    • Distinguish the applications and limitations of different chemical reagents in advanced organic synthesis.

    • Propose reasonable synthetic schemes, and illustrate reaction mechanisms that explain the outcomes of chemical transformations.

    • Evaluate current synthetic methods published in journal articles and review papers.

    Course overview

    The following table gives a general overview of the course structure. It suggests the amount of time you should allow for completing units and provides a broad schedule for you to plan your work. These times are intended as a guide only and should be adjusted to fit your personal needs more closely. You will need about 10–12 hours per week to work through the course. This estimation includes time for reading the units, completing activities, self-tests and assignments, attending tutorials, and preparing for you final examination.

    Unit Topic Study time
    (weeks)
    Assignment
    1 Reactivities and mechanisms 3
    (weeks 1–3)
     
    2 Carbon-carbon bond formation 4
    (weeks 4–7)
    Assignment 1
    (Units 1–2)*
    3 Reactive species and rearrangement 3
    (weeks 8–10)
     
    4 Asymmetric organocatalysis 3
    (weeks 11–13)
    Assignment 2
    (Units 3–4)*
    5 Case study of total synthesis 3
    (weeks 14–16)
    Assignment 3
    (All units)*
      Total 16  
    Working through this course

    Materials

    In addition to this Course Guide, the course has the following important components. Please ensure that you have all of these materials available.

    Study units

    There are five study units (four main topic areas plus one case file) in this course. Each unit includes several topics, each of which covers key concepts with corresponding examples to ensure your understanding. In addition to general concepts introduced by the online e-book, the study units will integrate topics based on journal articles and review papers that are current in the scientific world. This will help you identify current trends and key concepts in up-to-date research.

    This course covers four main areas in advanced organic chemistry, plus one case file:

    • reactivities and mechanisms: chemical kinetics, reaction mechanisms, and resonance stabilizations;

    • carbon-carbon bond formation: C–C, C=C bond formations, organometallic coupling and pericyclic reactions;

    • reactive species and rearrangement: reactions, migrations and rearrangements of carbocations, carbanions and free radicals;

    • asymmetric organocatalysis: including some asymmetric organic reactions with high enantioselectivities or diastereoselectivities using metal-free organocatalysts; and

    • a case study covering total synthesis: from planning, to application, to total synthesis of prostaglandins and taxol.

    Readings

    You may be instructed in the study units to read articles or other supplementary materials. These will be available online or provided as hard copies at the backs of the study units.

    E-Library E-Reserve readings

    You may be instructed to read articles in the E-Library E-Reserve. To read these items, go to the OUHK E-Library and click on 'E-Reserve'. Log in, click 'Accept/Agree' on the Copyright Restrictions page, fill in the 'Course Code' box, and click 'Search'.

    Set textbook

    You are required to read an online ebook subscribed to by the OUHK e-library ?as the course textbook:

    Narain, R P (2008) Mechanisms in Advanced Organic Chemistry, New Age International (P) Limited Publishers.

    To read the ebook, go to the OUHK E-Library and access it in either one of the following ways:

    • Click E-Reserve. Log in, click 'Accept/Agree' on the Copyright Restrictions page, fill in the 'Course Code' box, and click 'Search'.

    • Click E-books. Log in and input the title with double quotation marks.

    Sometimes you may not be able to access the book when someone is using it. Try again later. Remember to log out when you have finished using the ebook.

    In addition, the course will provide a list of reference journals that will be included in the study units folder and serve as a major component of the course materials.

    Supplementary readings

    Supplements to update the concepts in the set book will be included where necessary.

    In addition to these supplements, excerpts from the following sources will be integrated into the CHEM S445 course materials as core readings:

    Jones, M (2009) Organic Chemistry, 4th edn, Norton.

    Laue, T and Plagens A (2005) Named Organic Reactions, 2nd edn, Wiley.

    Audio visual materials/software

    Software for drawing chemical structures, ISIS Draw and ChemSketch, will be introduced to you. There are also online resources on the course learning platform Online Learning Environment (OLE). More information on the OLE will be provided in a later part of this Course Guide.

    Presentation Schedule

    The Presentation Schedule (Academic Timetable) is available on the OLE; it gives the dates for completing assignments, attending tutorials, surgeries, and laboratory sessions.

    Equipment requirements

    You will need access to a computer system with an Internet connection.

    Assessment

    CHEM S445 assesses your performance through three assignments, and a final examination. Continuous assessment and the final examination are the formal means of performance evaluation. Assignments account for 50% of the overall course score (OCS). The final examination at the end of the course makes up the remaining 50% of OCS. You are required to obtain 40% or above in both the overall continuous assessment score (OCAS) and the final examination to pass the course.

    The assessment elements in the course comprise assignments and a three-hour final exam. The weightings towards the overall course score (OCS) for each component are:

    • Assignment 1: 15%

    • Assignment 2: 15%

    • Assignment 3: 20%

    • Final exam: 50%

    Assignments

    There are three assignments for the course. You are required to submit all three assignments for the assessment of your understanding of different units. Your tutor will return your assignments with comments and feedback after marking. The contents for the assignments are as follows.

    • Assignment 1 consists of short questions that ask you to write reasonable reaction mechanisms and to identify the use of different reactants and reagents for organic synthesis in Units 1 and 2.

    • Assignment 2 contains more integrated questions compared to Assignment 1, involving material from Units 3 to 4.

    • Assignment 3 includes questions that ask you to plan a possible retro-synthetic scheme for large target molecules and to apply the suitable synthetic tools to real examples of organic synthesis.

    The assignment file will be made available on the OLE. Please access the OLE for further information.

    Final examination and grading

    The final exam covers all the content in your course materials. It counts for 50% of the overall course score. The format of the examination questions will be similar to those in your assignments. It will include both short and long questions. In addition to answering in words, you will sometimes be required to produce drawings of chemical structures, synthetic schemes or reaction mechanisms.

    Course assessment scheme

    Assessment Contribution to overall course score
    (OCS)
    Assignments 1-3 50%
    Final examination 50%
    Total 100%
    How to get the most from this course

    Tutors and tutorials

    Your tutor will give you extensive feedback on your assignments, as well as face-to-face tutorials and telephone tutoring, and online support.

    There are five two-hour tutorials and five two-hour surgeries for CHEM S445. At the tutorials your can discuss any problems or queries you may have. You don't have to attend these face-to-face tutorial sessions, but we do encourage you to do so. You should find them very helpful, and they will also give you a chance to meet your fellow students. The Tutorial and Surgery Timetable has the details. In addition, there will be three laboratory sessions for science experiments. Although they are not compulsory, you are also encouraged to attend all of them.

    Online Learning Environment (OLE)

    This course is supported by the Online Learning Environment (OLE). You can find the latest course information from the OLE. Through the OLE, you can communicate electronically with your tutor and course coordinator as well as other students. To access the OLE, you will need to have access to the Internet. The use of the OLE is required for the study of this course.

    Summary

    You are now studying a higher level course for the Honours Degree, so you should have already studied several courses in distance learning mode. You should have already developed the most comfortable method for you in your study. However, you are still recommended to set a timetable for your regular study. You will need around eight to ten hours a week to complete CHEM S445.

    If you have any questions during your study, don't hesitate to call your tutor and fellow students. Sometimes discussion with other people can help you to clarify ideas and concepts, and also strengthen your understanding.

    Good luck in the course, and also enjoy yourself!

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