Tetra-Tert-Butyl Methane – The Acyclic Alkane That Seemingly Should Exist

Chemistry, Education
The smallest non-cyclic alkane that theoretically should exist, but to date has never successfully been prepared, is tetra-tert-butyl methane. The reason it is so elusive is crowding or steric hindrance. Introducing TTBM Tetra-tert-butyl methane is the common name of 3,3-ditert-butyl-2,2,4,4-tetramethylpentane. A glimpse at the structure reveals the overcrowding. Despite the overcrowding, according to energy calculations, the molecule (we’ll call it TTBM) should be capable of existence. Assembling the Model Even building the model from its component parts presented a measure of difficulty. The 17 carbon atoms (black spheres) and 36 hydrogen atoms (smaller white spheres) required some effort to assemble into TTBM. Still, it was accomplished with all the component atoms not touching one another. What is the problem or problems? [caption id="attachment_16028" align="alignleft" width="405"] Molecular Model TTBM[/caption] Synthesis While…
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