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Chemistry · Ch 11 — Fundamentals of Organic Chemistry

Isomerism in Organic Compounds

11.5

Isomerism in Organic Compounds

Berzelius coined the term 'isomerism' for a phenomenon that turns out to be central to almost everything else in organic chemistry: two or more compounds can share EXACTLY the same molecular formula while still being genuinely different substances, differing in structure and consequently in physical properties, chemical properties, or both. Such compounds are called isomers, and the root cause of their differing behaviour is always one of two things -- a difference in bond CONNECTIVITY (which atoms are actually bonded to which), or a difference in spatial ARRANGEMENT (the same connectivity, but the atoms sit differently in three-dimensional space). …

Figure ~fig-isomerism-classification-treeClassification of isomers

What this figure shows. A flowchart headed 'ISOMERS (same molecular formula)' branching into 'Constitutional Isomers (Formerly structural isomers) (different in bond connectivity)' and 'Stereoisomers (same in bond connectivity)'. Constitutional isomers branch into Chain, Position, Functional, Metamers, Tautomers and Ring-Chain. Stereoisomers branch into Configurational (further split into Geometrical isomers and Optical isomers) and Co …