2/29/2012 - Synthesis of Diethylmagnesium

     Up to the point in 1866 there had been no way of synthesizing a magnesium organometallic compound without having attached a halide to the complex.  James Alfred Wanklyn (famous for methods of determining water quality) came up with a method of synthesis to exclude any presence of a halide anywhere in the synthesis.  This involved the use of Frankland's development of diethylmercury  and mixing it in dissolved magnesium yielding a mixture of diethylmagnesium and dissolved mercury.

(C₂H₅)₂Hg + Mg → (C₂H₅)₂Mg + Hg

2/28/2012 - Synthesis of Organochlorosilanes

   Again following the history of organometallics, a very important duo comes into the scene Charles Friedel, and James Mason Crafts (the brains behind the technology of Friedel-Crafts reactions) and harnessed their chemistry to the production of organochlorosilanes.  These molecules create the very important bond between a Carbon and a Silicon atom in many different mole ratios (up to 4 different Carbon-Silicon bonds around the silicon center).  The way this reaction is performed is through the addition between a silicon tetrachloride and a alkylzinc compound to produce the organochlorosilane and a zinc chloride salt.

SiCl₄ + (k/2)ZnR₂ →   R_kSiCl_4-k + (k/2)ZnCl₂

2/27/2012- Synthesis of Alkylaluminum Iodides

     Next in the realm of organometallic chemistry, taking place in 1859, was the creation of alkylaluminum iodides.  The scientists involved in the invention of this technology were Wilhelm Hallwachs (discovery of the photoelectric effect), and  A. Schafarik, when they took a mixture of dissolved aluminum and added a solution of alkyliodides (any primary R group).  This reaction produced a mixture of di-addition alkylaluminum iodide and mono-addition alkylaluminum iodide.

2Al + 3RI → R₂AlI + RAlI₂

Dimethylaluminum iodide

Methylaluminum iodide

2/26/2011 - Synthesis of Tetraethyllead

   Again, I apologize for the delay in posting due to my ailments, but I shall remain posting in the theme of organometallic history.  Just as a disclaimer, most of the information for these posts I have been gathering from Elshenbroich and Salzer's Organometallics 2^nd Eddition.  Following this chronology brings us to two other chemists studying in 1852, Carl Jacob Löwig (discoverer of the element bromine) and Eduard Schweizer.  While studying lead organometallics in Zürich, they became the first to prepare tetraethyllead by using ethyliodide and an allow of Sodium and Lead (much like the Frankland synthesis).

4NaPb + 4(C₂H₅) → (C₂H₅)₄Pb + 4Na + 3Pb

   Following this synthesis they continued to produce (C₂H₅)₃Sb and (C₂H₅)₃Bi

UBC Chemistry: Recommended Changes

   After completing (well on the verge of completion) I would like to note a couple of my suggestions of which pertain to the changes they should make in the program.  First off I would like to mention that there are no computer science credits required to complete this degree, and in my opinion this is wrong.  For the physical sciences of physics and chemistry, one of the growing fields in these two topics is the computational aspect.  Chemistry is no longer just experiments in the chemical world, but it also ventures into the tools of computing. At this point in my university career I regret not having taken one as I try with much difficulty to teach myself coding languages in the attempts to learn more computational skills. Also within the major program (already contained in the honours program) Chem 320: Structures of Atoms and Molecules demands to be a required course as it intros computational methods in chemistry.  The chemistry department does recognize the changing field, but it must look into enforcing these changes onto the students.
    Another change of which is needed is a history of chemistry course. Yes, this sounds redundant to learning the aspects of chemistry, but in my education I found myself bottling up all this theoretical knowledge without knowing how this theoretical knowledge was produced.  I have talked to a number of my graduating classmates and most of them agree that we have little knowledge of how the scientific method works.  So if the chemistry department was to enforce students to take a history course of chemical experiments I believe we will be more prepared to enter the world as scientists instead of entering the world as hardened students.  This idea came to me as one of my organic professors, who always gave small history lectures amidst the curricular lectures, taught me how this organic technology came to exist; with this knowledge I grasped a better understanding of what it was that creates a great discovery.
    This isn't a complete posting, so as I think of additional issues with the Chemistry program at UBC I will add them in here.  And in the next couple of days I will include a suggestions post for anyone starting out in the UBC chemistry program.

2/18/2012 - Synthesis of Dimethylmercury

    In the following years Edward Frankland continued researching organometallic compounds as he realized how much new chemistry can be harnessed from these studies.  In 1852 he branched into Mercury chemistry and then following into Tin and Boron reactions.  With these reactions he focused on simple methyl additions onto the metal creating a linear dimethylmercury through the reaction 2CH₃X + 2Na + Hg → (CH₃)₂Hg + 2NaX.  This dimethylmercury compound is extremely toxic, to the degree that one drop on a latex glove will absorb through and  absorbs into the skin and months later the fatality takes over.  And as stated before he transcended these alkylhalide reactions into adding different R groups onto Hg, Sn, and B.

2/17/2012 - Preparation of Ethyl Radical

    Bunsen took on students at Marburg, and one of those students was Edward Frankland  and he set out to synthesis an ethyl radical from the combination of 3C₂H₅I and 3Zn, thinking that would create ZnI₂ and 2C₂H₅, but instead revealed that the products were a pyrophoric liquid of (C₂H₅)₂Zn (diethylzinc), ZnI₂, and a solid of C₂H₅ZnI.  He also harnessed this technology to make the methyl analogue to synthesize dimethylzinc as well.  I do realize that I have already done a post regarding the synthesis of diethylzinc, but this here was the historical method of the first sythensis, different from todays methods.  Sorry again for my absences, I have been under a significant amount of pain.

2/11/2012 - Studies of Alkarsine Derivatives

   Then in 1840 Robert Bunsen continued the studies of the arsenic compounds synthesised in Paris a century earlier (cacodyl compounds).  He used these compounds to synthesize a numbed of derivatives of R₂As-AsR₂ into molecules (CH₃)₂AsCN.  After the synthesis Bunsen supposedly tasted this dangerous concoction, and luckily he lived to tell the tale.

 


Photo source

2/10/2012 - Synthesis of Zeise's Salt

     The next advancement in organometallic chemistry didn't happen until 1827 by a Danish chemist by the name William Christopher Zeise in Copenhagen.  When this compound was first synthesized, chemists were baffled on what the molecular structure of this grand molecule was. It wasn't until recently that it was determined to be a square planar complex where the ethylene molecule coordinated to the Platinum in a η² fashion (meaning that it was the bond of the ethylene that was bonding).  The synthesis happened when Zeise was PtCl₄ being boiled in ethanol to create the final salt of K[PtCl₃(η²-C₂H₂)]-H₂O.

2/9/2012 - Cacidyl oxide synthesis

     As an apology for my absence my next couple of reactions will follow along the chronological order for the history of organometallic chemistry.  The first ever synthesis of an organometallic occured in Paris, in 1760, at a military pharmacy, where there was a cadet who was working in creating synthetic inks containing cobalt salts, and in extracting the cobalt from the raw form arsenic was removed.  In this removal the As₂O₂ is combined with CH3COOK to produce a fuming liquid containing the organometallic product of [(CH₃)₂As]₂O (also known as Cacidyl oxide)

2/2/2012 - Stille Reaction

   This organometallic catalyzed reaction causes the creation of a carbon carbon bond between an organotin compound (R¹SnBu₃) and an sp² hybridized organohalide (R²-X). The reaction can be thought of as in a reaction cycle to better visualize the reactions going on here. The catalyzing material here is the Paladium complex with a number of variable ligands surrounding it. This reaction was discovered by the chemist John Kenneth Stille in 1977 and is continued to be used in many organic synthesis processes used for molecules of biomedical significance.

Methane Storage

    Here is a wonderful video that I found while looking through a number of science educational videos.  Something that I've always found interesting is the creation of educational videos, and I think this one is wonderful.