Please note! Course description is confirmed for two academic years (1.8.2018-31.7.2020), 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: 02.03.2021 - 15.04.2021

Teacher in charge (valid 01.08.2020-31.07.2022): Jan Deska

Teacher in charge (applies in this implementation): Jan Deska

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

CEFR level (applies in this implementation):

Language of instruction and studies (valid 01.08.2020-31.07.2022):

Teaching language: English

Languages of study attainment: English

CONTENT, ASSESSMENT AND WORKLOAD

Content
  • Valid 01.08.2020-31.07.2022:

    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 01.08.2020-31.07.2022:

    The course is assessed through

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

Workload
  • Valid 01.08.2020-31.07.2022:

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

DETAILS

Study Material
  • Valid 01.08.2020-31.07.2022:

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

Prerequisites
  • Valid 01.08.2020-31.07.2022:

    CHEM-E4150 Reactivity in Organic Synthesis or equivalent

FURTHER INFORMATION

Description

Registration and further information