OrganoSilicon Compounds Peter H.M. Budzelaar. OrganoSilicon Compounds 2 Organosilicon compounds Silicon is just like carbon, but: Larger –five- and six-coordinate.

Slides:



Advertisements
Similar presentations
GROUP IV.
Advertisements

4.5 Physical Properties in Giant Covalent Substances
Organic Synthesis Notation
Organometallic Chemistry an overview of structures and reactions
MUDDLE YOUR WAY THROUGH ORGANIC MECHANISMS KNOCKHARDY PUBLISHING A VERY BRIEF INTRODUCTION 2008 SPECIFICATIONS.
CHAPTER 7 Haloalkanes.
Alkyl halides, Alcohols, Ethers, Thiols. Required background: Acidity and basicity Functional groups Molecular geometry and polarity Essential for: 1.
Advanced Higher - Unit 3 Permeating aspects of organic chemistry.
Organic Reactions. Point #1 3 basic kinds of reactions A) Addition Reactions (like synthesis reactions) Hydrogenation – saturating an unsaturated carbon.
Organic Reactions Dr. M. Abd-Elhakeem Faculty of Biotechnology Organic Chemistry Chapter 3.
Main-group Organometallics Peter H.M. Budzelaar. Main-Group Organometallics 2 Main group organometallics at a glance Structures –  bonds and 3c-2e (or.
The Structures of Magmas No Phase Diagrams!. The Structures of Magmas Melt structure controls: The physical properties of magmas The chemical behaviour.
Transition-metal Organometallics
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Reactions of Aldehydes and Ketones.
OrganoLithium Compounds Peter H.M. Budzelaar. OrganoLithium Compounds 2 Organo-lithium compounds Ionic character, electron-deficient –oligomeric or polymeric.
Ligand Substitution Reactivity of Coordinated Ligands Peter H.M. Budzelaar.
Carbenes and Olefin Metathesis Peter H.M. Budzelaar.
Structure of Amorphous Materials -2  Oxide glasses  Metallic glasses  Amorphous Polymers  Silicon.
Organometallic Chemistry an overview of structures and reactions Peter H.M. Budzelaar.
John E. McMurry Paul D. Adams University of Arkansas Chapter 10 Organohalides.
Organic Reactions Larry Scheffler Lincoln High School IB Chemistry 3-4 Version
Organometallic Reagents: Sources of Nucleophilic Carbon for Alcohol Synthesis 8-7 If the carbonyl carbon of an aldehyde or ketone could be attacked by.
Lecture 34 MO’s of the most important polyatomic ligands 1) Bonding in carbene complexes Transition metal carbene complexes are formed by carbenes, CX.
Intermolecular Forces
CHEMISTRY PART 2 Periodic Table. Chemistry – Recall  Chemistry is the study of matter and the changes it undergoes  Physical Properties: cause a physical.
1 Chapter 13 Silicon reagents  General features  Two other highly important properties of silicon  Reactions of organosilanes  1,2 rearrangements (Brook.
ALKENE AND ALKYNE REACTIONS and SYNTHESIS Dr. Sheppard CHEM 2412 Summer 2015 Klein (2 nd ed.) sections 11.7, 9.1, 9.3, 11.10, , 9.8, 9.7, 14.8,
Increasing polarizability improves nucleophilic power.
Introduction to the Chemistry of Organosilicon Compounds Comparing silicon chemistry with carbon chemistry CH 4 (methane)SiH 4 (silane) bp: -161ºCbp: -112ºC.
AP Biology The Chemistry of Life AP Biology Why are we studying chemistry? Chemistry is the foundation of Biology.
Chemical Reactions and Enzymes. Parts of a Chemical reaction  Reactant: the elements or compounds that enter into a chemical reaction  Product: the.
Organic Chemistry 10 Chemistry. Quiz Alkanes General Formula Description Combustion Reactivity Chemical test Uses C n H 2n+2 Saturated Burns in Oxygen.
Organic Reactions Larry Scheffler Lincoln High School IB Chemistry 3-4 Version
Organic Reactions Version 1.4. Reaction Pathways and mechanisms Most organic reactions proceed by a defined sequence or set of steps. The detailed pathway.
Organic Chemistry. What is organic chemistry? All biological molecules – simple sugars to complex nucleic acids All fossil fuels – including oil, coal,
Unit 3: Reactions of Alkenes. Thermodynamics and Kinetics
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Reactions of Aldehydes and Ketones.
Chapter 21 The Radical Chemistry
Carbon Group mike alexander period 4 10/21/11. Groups & Chemical Properties Carbon chemical property of carbon is that it can create 4 covalent bonds.
The CHEMISTRY of Life CHEMISTRY is the foundation of BIOLOGY.
Lesson declared Hydroxide and oxide After finished this lesson student will to able to # Say about the Hydroxide # Say about Hydroxide ion. # Say about.
An Alternative Semiconductor Definition!
Why Addition Reactions Proceed: Thermodynamic Feasibility 12-1 Because the C-C  bond is relatively weak, alkene chemistry is dominated by its reactions.
Introduction to Organic Chemistry Section Organic Chemistry The chemistry of carbon compounds Not including metal carbonates and oxides Are varied.
An unknown molecule A has 4 signals in the 1 H NMR spectrum. Which of the following corresponds to molecule A.
SILANES H Hydrides of Silicon are known as Silanes. Sin H2n+2 (n ups 7) Silanes (also known as saturated hydrosilicons) consist only of Si and H atoms.
Alkanes Alkanes are fully saturated hydrocarbons
SILICONES AND PHOSPHAZENES. Silicones and phosphazenes are examples of inorganic Polymers. Inorganic elements can have different valencies Than carbon.
CHEMISTRY PART 2 Periodic Table.  Atomic Number = # of protons  If the atom is neutral:  Atomic Number = # of electrons  Atomic Mass = # of protons.
CHEMISTRY PART 2 Periodic Table.  Atomic Number = # of protons  If the atom is neutral:  Atomic Number = # of electrons  Atomic Mass = # of protons.
Ionic Reactions Nucleophilic Substitution and Elimination Reactions of Alkyl Halides.
© 2016 Pearson Education, Inc. Alkenes Structure, Nomenclature, and an introduction to Reactivity Thermodynamics and Kinetics Paula Yurkanis Bruice University.
Chlorination of Higher Alkanes
University of California,
Chemistry Spaced Learning Triple
Chemistry Part 2 Periodic Table.
Dr. S. B Maulage Dept of Chemistry.
9.4 – NOTES Petroleum and Chemical Bonding
OrganoLithium Compounds
George Lebo 24 October 2012 AST 2037
Organolithium Compounds
Figure Number: CO Title: Figure 10.5
Introduction Main Group Metals
ORGANIC CHEMISTRY.
Chemistry – Jan 9, 2018 P3 Challenge- Agenda Bonding HMK reivew
Chemistry – Jan 9, 2018 P3 Challenge- Objective –
Organometallic Chemistry
Substitution Reactions:
Catalyst If an element has 19 protons… What element is it?
Organometallic Chemistry
Presentation transcript:

OrganoSilicon Compounds Peter H.M. Budzelaar

OrganoSilicon Compounds 2 Organosilicon compounds Silicon is just like carbon, but: Larger –five- and six-coordinate structures positive More electropositive –easier attack by nucleophiles Does not want to form multiple bonds –SiO 2 vs CO 2 Organo Ge etc... compounds: slow transition to more typical metal chemistry; M II becomes more stable for Pb

OrganoSilicon Compounds 3 Bonds to silicon Si-Cbond covalent, unreactive Si-O, Si-Fvery ("abnormally") strong Si-Cl, Si-Br, Si-Ireactive Si-Siweak (!) Si=Si and Si=Cweak, very reactive

OrganoSilicon Compounds 4 Silicones !

OrganoSilicon Compounds 5 Silicones Based on strong -Si-O- backbone –a pure -Si-Si- backbone would be weak "Slick" Viscosity change little with temperature –silicone oil Easy chemical modification and/or attachment to a surface –Silan –Silylation of GC column surfaces

OrganoSilicon Compounds 6 The Si-O-Si bond Si-O-Si flexible Is also seen in structures of SiO 2 No d  -p  bond !!!! Ph 3 COCPh 3  COC = 128° Ph 3 SiOSiPh 3  SiOSi = 159°

OrganoSilicon Compounds 7 Chain folding - silicones vs alkanes At low temperatures, both alkanes and silicones prefer to form extended chains At higher temperature: For alkanes, the main change is formation of "gauche defects", i.e. partially folded chains. –Reduces contacts between chains, lowers viscosity For silicones, a wider range of Si-O-Si angles will occur, mainly around 180°, resulting in more extended chains –Increases contacts between chains –Counteracts the "normal" viscosity decrease, so viscosity stays nearly constant –Very useful for high-temperature synthetic lubricants

OrganoSilicon Compounds 8 Synthesis Direct synthesis –Si is not electropositive enough for unassisted direct synthesis –An Si/Cu alloy works better: Metathesis Hydrosilylation Catalyzed/initiated by light, free radicals, many transition metal compounds.

OrganoSilicon Compounds 9 Reactivity Nucleophilic attack Electrophilic attack (on C!) With halogens R 3 Si often behaves like a "large hydrogen"

OrganoSilicon Compounds 10 Sterics down group IV Ph 4 CPh 4 SiPh 4 Ge Ph 4 SnPh 4 Pb

OrganoSilicon Compounds 11 Higher coordination numbers Ph 4 Si 4-coordinate Ph 3 SiF coordinate Ph 2 Si(tropolonate) 2 6-coordinate

OrganoSilicon Compounds 12 Maybe not useful, but certainly beautiful C 6 (SiMe 2 OMe) 6