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Chemistry · Ch 14 — Basic Principles of Organic Chemistry

Structural Representation of organic molecules

14.2

Structural Representation of organic molecules

Before any of a molecule's chemistry can be discussed, it first has to be represented clearly on paper. A structural (or 'dash') formula does this most fully: every atom in the molecule is written out with its own symbol, and every covalent bond between two directly-bonded atoms is drawn as a single dash connecting them. For methane, CH4, this means drawing the central carbon symbol with four separate dashes radiating out to four separate H symbols. An electron-dot (Lewis) structure carries the same information in a different visual form: instead of a dash, every valence electron of every atom is drawn explicitly as a dot around that atom's symbol, and a shared covalent bond is shown as a PAIR of dots sitting between the two bonded atoms. In methane's electron-dot structure, each of the four C-H bonds is drawn as its own pair of dots between C and that particular H -- so overall carbon is surrounded by four such bonding pairs (eight dots), with no additional lone-pair dots left over on carbon, since methane's carbon uses every one of its four valence electrons in bonding. Because a full structural or electron-dot formula becomes unwieldy for anything beyond the smallest mo …

Figure 14.2-aStructural (dash) formula of methane

What this figure shows. Methane's structural formula drawn with the central carbon joined to four hydrogen atoms by four dashes (single bonds) arranged around it -- one to the H above, one to the H below, and one each to the H on the left and right, i.e. a plus-sign-like arrangement of four C-H dashes on flat paper (the true tetrahedral 3-D shape is not shown by this …

Figure 14.2-bElectron-dot (Lewis) structure of methane

What this figure shows. The same methane molecule redrawn with every valence electron shown as a dot: each of the four C-H bonds is shown as a pair of dots sitting between the C and that H, so the carbon is surrounded by four such bonding electron pairs (8 dots total around C, none left over as lone pairs, since carbon has no lone pairs in methane and each H has only its one shared pair, comple …