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Chemistry · Ch 11 — Fundamentals of Organic Chemistry

Structural Representation of Organic Compounds

11.4

Structural Representation of Organic Compounds

Because the source textbook prints this section's own heading as '11.2 Structural representation of organic compounds' -- reusing the number already assigned to the Classification section earlier in the chapter -- it has been renumbered 11.4 here, in its true reading position between Nomenclature and Isomerism, so that every section in this chapter carries one unique, sortable number; the content itself is unchanged.

A molecular formula (say, C3H8O) is the least informative way to describe a compound -- it fixes only the ratio of atoms present, saying nothing about how they are connected. Chemists build up from there through an increasingly compact hierarchy of structural representations. A Lewis (dot) structure shows every atom and every bonding/lone electron pair explicitly. Replacing each shared electron pair with a dash gives the dash (line-bond) structure: a single line is one sigma bond, a double line is a double bond (one sigma, one pi), a triple line is a triple bond (one sigma, two pi), and lone pairs on heteroatoms may or may not be drawn in. Abbreviating that dash structure further -- dropping some or all of the bond lines and using a subscript to show how many identical groups sit on one atom -- gives the condensed structural formula (CH3-CH2-CH2-OH for n-propanol). The most compact representation of all is the bond-line (skeletal, zig-zag) structure, used almost universally by working organic chemists: carbon and hydrogen atoms are not written at all, carbon-carbon bonds are drawn as a zig-zag of plain lines, and only heteroatoms (O, N, Cl, and so on …

Table ~table-structural-representationsMolecular formula, complete structural formula, condensed structure and bond-line structure, compared
CompoundMolecular formulaCondensed structureBond-line structure (description)
n-propanolC3H8OCH3-CH2-CH2-OHA 3-carbon zig-zag with -OH at the end
1,3-butadieneC4H6CH2=CH-CH=CH2A 4-carbon zig-zag with double bonds at both ends (drawn with double lines)
t-butyl chlorideC4H9ClCH3-C(CH3)(CH3)-Cl, i.e. (CH3)3CClA central point with three short line branches (methyls) and one bond to -Cl