Learn · Organic Chemistry

Types of Isomers

Same molecular formula, different compound — sorted into a simple family tree.

Quick answer Isomers are different compounds that share the same molecular formula, split first into constitutional isomers (different connectivity) and stereoisomers (same connectivity, different 3-D arrangement). Stereoisomers then divide into enantiomers, which are non-superimposable mirror images, and diastereomers, which are stereoisomers that are not mirror images.

1. Constitutional isomers have different connectivity

Constitutional (structural) isomers share a molecular formula but bond their atoms together in a different order.

Butane
Isobutane (constitutional isomer)
Ethanol (C₂H₆O)
Dimethyl ether (same formula)

2. Stereoisomers share connectivity but differ in space

Stereoisomers connect the same atoms in the same order yet arrange them differently in three dimensions.

(E)-2-butene
(Z)-2-butene (stereoisomer)

3. Enantiomers are non-superimposable mirror images

Enantiomers are stereoisomers related as left and right hands — mirror images that cannot be overlaid.

(R)-2-bromobutane
(S)-2-bromobutane (its enantiomer)

4. Diastereomers are stereoisomers that are not mirror images

Diastereomers differ in 3-D arrangement without being mirror images — including cis/trans and E/Z alkenes.

2-butene backbone
(E)- and (Z)-2-butene are diastereomers

5. Summary

Same formula · different connectivity = constitutional · same connectivity + 3-D difference = stereoisomers · mirror image = enantiomers · not a mirror image = diastereomers.

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Constitutional (structural) isomers — same molecular formula, different atom connectivity.

Enantiomers — a pair of stereoisomers that are mirror images of each other.

Diastereomers — they are stereoisomers, but they are not mirror images of one another.

Connectivity: stereoisomers keep the same atom-to-atom bonding and differ only in 3-D arrangement, while constitutional isomers bond the atoms in a different order.

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