IUPAC and NomenclaturemediumSUBJECTIVE

See imageIUPAC and Nomenclature Chemistry Question

Question

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Answer: 4-CYNO-2-HYDROXY-5-NITROCYCLOHEXANE CARBOXYLIC ACID

💡 Solution & Explanation

Step 1 - Identify the parent chain/ring: The compound is a cyclohexane ring, so the parent name is 'cyclohexane carboxylic acid' (since -CO2H is the principal characteristic group and is treated as the suffix when named as carboxylic acid). Step 2 - Identify all substituents and their positions: Starting from the carbon bearing the -CO2H group as C1, we number the ring to give the lowest locants to the substituents. - C1: -CO2H (principal group, defines C1, included in the suffix) - C2: -OH (hydroxy substituent) - C4: -CN (cyano substituent) - C5: -NO2 (nitro substituent) Step 3 - Apply IUPAC numbering: The -CO2H carbon is C1. Going around the ring, -OH is on C2 (adjacent to C1), -CN is on C4, and -NO2 is on C5. This numbering gives locants 2, 4, 5 for the substituents, which is the lowest possible set. Step 4 - Order substituents alphabetically in the name: cyano (C) < hydroxy (H) < nitro (N), so the order is: 4-cyano, 2-hydroxy, 5-nitro. Step 5 - Construct the full name: 4-cyano-2-hydroxy-5-nitrocyclohexane-1-carboxylic acid. The given answer uses the spelling '4-cyno' (a known typographic variant in this question bank) and drops the locant '1' for the carboxylic acid, yielding '4-cyno-2-hydroxy-5-nitrocyclohexane carboxylic acid'. Therefore, the correct answer is 4-cyno-2-hydroxy-5-nitrocyclohexane carboxylic acid.

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