CHEM-E4195 - Selectivity in Organic Synthesis, Lecture, 1.3.2022-14.4.2022

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Please note! Course description is confirmed for two academic years, which means that in general, e.g. Learning outcomes, assessment methods and key content stays unchanged. However, via course syllabus, it is possible to specify or change the course execution in each realization of the course, such as how the contact sessions are organized, assessment methods weighted or materials used.

LEARNING OUTCOMES

After the course the student will be able to

  • list effects contributing to regioselectivity & diastereoselectivity
  • describe shape and properties of frontier orbitals of typical organic functional groups
  • explain intramolecular interactions related to stereoelectronics
  • apply the concepts of control by polarity, orbital geometry, or sterics to predict the outcome of stereo- or regioselective reactions
  • propose suitable reagents or reaction conditions to selectively synthesize organic molecules with emphasis to position or relative configurations of functional groups

Credits: 5

Schedule: 01.03.2022 - 14.04.2022

Teacher in charge (valid for whole curriculum period):

Teacher in charge (applies in this implementation): Suvi Holmstedt

Contact information for the course (applies in this implementation):

CEFR level (valid for whole curriculum period):

Language of instruction and studies (applies in this implementation):

Teaching language: English. Languages of study attainment: English

CONTENT, ASSESSMENT AND WORKLOAD

Content

  • valid for whole curriculum period:

    The selective assembly of molecular structures in terms of positions or relative configurations of functional groups represents a crucial skill in modern organic synthesis, and a prerequisite in the production of fine chemicals, pharmaceuticals and agrochemicals.

    This course takes up previously reviewed organic transformations and discusses them in the context of regio- and diastereoselectivity. The Selectivity course will provide the tools to perform conformational analyses and employ general concepts such as polarity control and orbital control to predict reaction outcomes and relative configurations in C-C and C-heteroatom bond forming transformations. Reactions will include the addition of simple carbon nucleophiles, enolates and P-, S-, and Si-stabilized carbanions to carbonyls and olefinic double bonds as well as cycloadditions and rearrangements.   

Assessment Methods and Criteria

  • valid for whole curriculum period:

    The course is assessed through

    • four online quizzes (week 9 - week 14), and
    • an oral examination (week 15)

Workload

  • valid for whole curriculum period:

    Lectures 18 h
    Exercise discussions 18 h
    Online quizzes 12 h
    Self-studies 87 h

DETAILS

Study Material

  • valid for whole curriculum period:

    Clayden, Greeves, Warren, Wothers: Organic Chemistry; chapters 27, 32-35
    Brückner, Harmata: Organic Mechanisms; selected material

Substitutes for Courses
Prerequisites

FURTHER INFORMATION

Further Information

  • valid for whole curriculum period:

    Teaching Period:

    2020-2021 Spring IV

    2021-2022 Spring IV

    Course Homepage: https://mycourses.aalto.fi/course/search.php?search=CHEM-E4195

    Registration for Courses: In the academic year 2021-2022, registration for courses will take place on Sisu (sisu.aalto.fi) instead of WebOodi.

    Sisu

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Aalto University Code of Academic Integrity and Handling Violations Thereof