Skip to content

Chemistry · Ch 14 — Basic Principles of Organic Chemistry

Bond line formula or zig-zag formula

14.2.2

Bond line formula or zig-zag formula

A bond-line (or zig-zag) formula goes a step further than a condensed formula by dropping the element symbols for carbon and hydrogen entirely, keeping only the bond lines themselves. Every carbon-carbon bond is drawn as a segment of a zig-zag line; each of the TWO END points of that zig-zag line represents a terminal methyl (CH3) group, and every INTERNAL vertex (every point where the line changes direction, i.e. every 'kink') represents one carbon atom, understood to be carrying however many hydrogen atoms are needed to bring it up to its normal four bonds (its tetravalency). Propane, CH3-CH2-CH3, is therefore drawn as just a simple two-segment zig-zag line -- no atom symbols at all are needed, since both end vertices are automatically read as CH3 and the one middle vertex is automatically read as CH2. The one deliberate exception to 'omit everything except carbon skeleton bonds' is that heteroatoms (any atom that is not carbon or hydrogen) are always written out in full, and so is any hydrogen that happens to be bonded directly to such a heteroatom -- so ethanol, C2H5OH, is drawn as a …

Table 14.1Representation of structural formula (Try this -- complete the table)

Table 14.1 asks students to complete, across the four representations (dash formula / condensed formula A / condensed formula B / bond-line or zig-zag formula), the same set of five compounds. Row 1 is worked in full as the model: dash formula H-C-C-C-C-H (n-butane, all H's shown), condensed formula A = CH3(CH2)2CH3, condensed formula B = CH3-CH2-CH2-CH3, and the corresponding two-segment-longer (three-segment) zig-zag bond-line formula. Row 5 is cued as a dash formula for a dinitrile-type structure, N≡C-C-C≡N with H and OH labels also present in the source. NOTE ON SOURCE FIDELITY: rows 2, 3 and 4 of this table print no legible cell content in the extracted source text at all (the table's 2-D cell layout did not survive extraction, consistent with this chapter's known garbling risk for structural diagrams), and row 5's exact substitution pattern (why an OH label appears alongside a dinitrile skeleton) could not be reliably resolved …