Module Details

The information contained in this module specification was correct at the time of publication but may be subject to change, either during the session because of unforeseen circumstances, or following review of the module at the end of the session. Queries about the module should be directed to the member of staff with responsibility for the module.
Title CHEM431 - Main Group Organic Chemistry
Code CHEM431
Coordinator Dr IA O'Neil
Chemistry
Ion@liverpool.ac.uk
Year CATS Level Semester CATS Value
Session 2021-22 Level 7 FHEQ First Semester 7.5

Pre-requisites before taking this module (or general academic requirements):

 

Aims

The aim of this module is to broaden and extend the knowledge of modern Organic Chemistry so that students will be able to enter directly into a PhD or embark on a career as a specialist chemist.


Learning Outcomes

(LO1) By the end of the module students will have achieved a solid foundation in Organic Chemistry. In particular they will have a clear understanding of Main Group Organic Chemistry and Organopalladium Chemistry and be able to give examples of their use in modern synthetic methodology.

(S1) Students will develop their chemistry-related cognitive abilities and skills, ie abilities and skills relating to intellectual tasks, including problem-solving as required by the Chemistry subject benchmark statement. In particular, at master's level, they will gain the ability to adapt and apply methodology to the solution of unfamiliar problems.


Teaching and Learning Strategies

The lecture material will be delivered asynchronously in short video recordings. The material presented will be supported by two 1.5 hour tutorials and additional corrected exercises available online. The corrected exercises will not be assessed.


Syllabus

 

Main Group Organic Chemistry
• Chemistry of Lithium: Lithium amide bases, structure and aggregation of organolithiums. Use of sterically hindered bases in controlling enolate formation via kinetic deprotonation. Lithium mediated cyclisation reactions. α-Heteroatom functionalised organolithiums. Transmetallation of organolithiums. Modern application of Grignard reagents.
• Chemistry of Boron: Structure and synthesis of organoboranes. Hydroboration reaction. Reactions of organoboranes. Introduction of heteroatoms via borane intermediates. Use of organoboranes in the synthesis of carbon-carbon bonds. Chemistry of allylboranes.
• Chemistry of Silicon: Comparison of silicon and carbon compounds. Peterson olefination. Chemistry of vinyl, aryl silanes and allylsilanes. Silyl enol ethers, formation and reactions.
• Chemistry of Tin: Synthesis of tin compounds. Transmetallation reactions. Chemistry of vinyl and allyl stannanes. Tin hydr ides and their use in radical mediated reactions.

Organopalladium Chemistry
• Fundamental mechanistic steps: Ligand variation, bonding modes, oxidative addition, reductive elimination, migratory insertion, carbonylation, β-hydride elimination.
• Palladium (II) catalysed C-C formation: Heck simple and tandem processes, isomerisation. Nucleophilic addition to alkenes - Wacker, heterocycle synthesis, catalytic option.
• Palladium (0) catalysed bond formation: C-C Stille and Suzuki couplings with optional carbonylation, Sonogashira alkyne coupling. C-X Formation of amines, sulfides, phosphines etc.
• π-allyl Complexes: Alkylation, mechanism, stereo- and regiochemistry. Carbonates and epoxides - in situ base formation. Intramolecular examples.Trimethylenemethane complexes, [3+2] cycloadditions.


Recommended Texts

Reading lists are managed at readinglists.liverpool.ac.uk. Click here to access the reading lists for this module.

Teaching Schedule

  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours     3

    18

21
Timetable (if known)              
Private Study 54
TOTAL HOURS 75

Assessment

EXAM Duration Timing
(Semester)
% of
final
mark
Resit/resubmission
opportunity
Penalty for late
submission
Notes
formal remote written examination  120 minutes    80       
CONTINUOUS Duration Timing
(Semester)
% of
final
mark
Resit/resubmission
opportunity
Penalty for late
submission
Notes
Assignment will consist of two tutorials, each 90 minutes long (20%)  3 hours    20