Branched hydrocarbons

How can we name the structure (a)?

(a)

[Sn(CH3)3H] hydridotrimethyltin (additive) trimethylstannane (substitutive)

von Hofmann’s footnote

Systematic name formation in chemistry typically happens through compounding, derivation, or mix of both. The semantic modification of a combining form through umlaut-like vowel change as seen in alkanes/alkenes/alkynes appears to be unique. Its origin could be traced to the 1866 publication of August Wilhelm von Hofmann [1]; I probably would never know about it if not for an illuminating blog post by Joe Dixon [2].

In an extended footnote, Hofmann proposed to call the first ten alkanes as follows: methane, ethane, propane, quartane, quintane, sextane, septane, octane, nonane and decane.

Carbon chains

Introduction aside, almost every organic chemistry textbook begins with alkanes, that is, acyclic hydrocarbons with the general formula C_nH_2n+2. Maybe because of that, chemists tend to think of their naming as something too basic and thus boring. I myself thought so until coming across the book by Edward Godly [1] who, in a stroke of genius, put the chapter on silicon chains [1, pp. 19—21] before the chapter on hydrocarbon chains [1, pp. 25—28]. It prompted me to compare the naming of the two classes side-by-side.