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Stereoisomeric olefins, cycloalkanes, etc. which differ in the positions of groups relative to a reference plane: in the cis-isomer the atoms are on the same side, in the trans-isomer they are on opposite sides. An obsolete synonym, for which the usage is strongly discouraged, is geometric isomerism.

12 votes

Can geometrical isomers be enantiomers?

Technically, this double bond should not be labelled as (E)- or (Z)-. It is what is known as an enantiomorphic double bond, for which the proper stereodescriptors are seqCis and seqTrans. This is des …
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11 votes

Stereoisomerism in 1,2-cyclobutanediol

These two isomers are enantiomers, i.e. mirror images, of each other: $\hspace{50 mm}$ This one has a plane of symmetry through the molecule and is therefore meso: $\hspace{60 mm}$
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4 votes

Why is the 'side' of a double bond defined across the double bond horizontally rather than v...

You can still get isomers from "the other line"; it's just that they aren't cis/trans [or (E)-/(Z)-] isomers. The reason why cis/trans isomers are "special" is that the molecular connectivity is the s …
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4 votes
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What type of isomers are cis-but-2-ene and 2-methylpropene?

(2​Z)-But-2-ene and 2-methylprop-1-ene are constitutional isomers as they have different connectivities, i.e. the sequence in which the atoms are bonded to each other is not the same. For example, the …
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