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Organic Chemistry – Some Basic Principles and Techniques

Structural representations

Interconvert structural formulas.

Organic structures can be written in several ways, from the fullest to the shortest:

  • A complete (Lewis or dash) formula shows every atom and every bond. Ethanol drawn out fully shows all its C–H, C–C, C–O and O–H bonds.
  • A condensed formula groups the atoms on each carbon: ethanol is CH₃CH₂OH. Repeated units can be bracketed: HO(CH₂)₃CH(CH₃)CH(CH₃)₂ has three CH₂ groups in a row.
  • A bond-line formula is the shortest: a zigzag line. Each corner and each end is a carbon atom, with as many hydrogens as it needs to make four bonds; the hydrogens on carbon are not drawn. Atoms other than C and H (O, N, Cl…) are written in.

For example, butane, CH₃CH₂CH₂CH₃, is a zigzag of three lines with four points (two ends and two corners), one for each carbon.

Rings are drawn as polygons: join the two ends of propane's chain and you get cyclopropane, a triangle. Cyclopentane is a pentagon; cyclohexane a hexagon.

To show the 3-D shape on flat paper, chemists use wedges:

  • a solid wedge: a bond coming out of the page, towards you;
  • a dashed wedge: a bond going into the page, away from you;
  • a plain line: a bond lying in the plane of the page.
Corners and ends are carbons.

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