MolSynapsequestion bank
MolSynapse / Question bank / IUPAC Nomenclature and Structural Isomerism / Nomenclature of bicyclic, spiro and aromatic compounds
JEE Advanced levelSingle correct optionDifficulty 3 of 3nm147

A cyclobutane ring and a cyclohexane ring share one carbon. An -OH group is on the cyclobutane carbon adjacent to the shared atom, and a chlorine atom is on the cyclohexane carbon adjacent to the shared atom. The IUPAC name is

  1. A1-chlorospiro[3.5]nonan-5-ol
  2. B5-chlorospiro[3.5]nonan-1-ol
  3. C5-chlorospiro[5.3]nonan-1-ol
  4. D9-chlorospiro[3.5]nonan-1-ol

Answer: B

The descriptor is [3.5] (smaller ring first). Numbering begins at a small-ring atom next to the spiro atom, giving the principal group (OH) the lowest locant: C-1 = the carbinol carbon, C-2, C-3, spiro C-4, then C-5 onward in the six-membered ring. The chlorine carbon next to the spiro atom is C-5 (lowest choice). Alphabetical prefix chloro precedes the suffix ol: 5-chlorospiro[3.5]nonan-1-ol.
Practice IUPAC Nomenclature and Structural Isomerism More on Nomenclature of bicyclic, spiro and aromatic compounds

More questions on Nomenclature of bicyclic, spiro and aromatic compounds