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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.

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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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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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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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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