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 MAIN GROUP ORGANIC CHEMISTRY 1: C OPTION
Code CHEM431
Coordinator Dr IA O'Neil
Chemistry
Ion@liverpool.ac.uk
Year CATS Level Semester CATS Value
Session 2014-15 M Level First Semester 7.5

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

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
  • Organopalladium Chemistry
and be able to give examples of their use in modern synthetic methodology.

Syllabus
1  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. R2NH effect. Lithium mediated cyclisation reactions. α-Heteroatom functionalised organolithiums.
  • Chemistry of Boron Structure and synthesis of organoboranes. Hydroboration reaction. Reactions of organoboranes. Introduction of heteroatoms via borane intermediates. Allylboranes and boron enolates.
  • 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 hydrides 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.

Teaching and Learning Strategies

Lectures

Worked examples presented in lectures

Material is presented via a series of lectures. Learning is supported via worked examples and students are directed to ChemTube3D software.


Teaching Schedule
  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours 18

           18
Timetable (if known)              
Private Study 57
TOTAL HOURS 75

Assessment
EXAM Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
Unseen  2 hours  Semester 1  100  Yes  Standard UoL penalty applies  August resit for PGT students if applicable. Integrated Master's students resit at the next normal opportunity.  
CONTINUOUS Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
             

Recommended Texts
  • Organic Chemistry, J. Clayden, N. Greeves, S. Warren and P. Wothers, OUP, 2nd edition 2012
  • Organic synthesis : the roles of boron and silicon, S. E. Thomas, OUP
  • Palladium reagents and catalysts: innovations in organic synthesis, J. Tsuji, Wiley
  • Handbook of palladium-catalyzed organic reactions: synthetic aspects and catalytic cycles, J-L, Malleron, Academic Press
  • Palladium reagents in organic syntheses, R.F. Heck, Academic Press