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JEE Advanced levelSingle correct optionDifficulty 3 of 3nm090

A cyclohexene ring bears an OH group on a ring carbon directly attached to a C=C carbon, and a methyl group on the ring carbon para (1,4) to the OH-bearing carbon, on the same side as the C=C (the C=C is C-2=C-3 and methyl is on C-4). The IUPAC name is:

  1. A4-methylcyclohex-2-en-1-ol
  2. B5-methylcyclohex-2-en-1-ol
  3. C4-methylcyclohex-5-en-1-ol
  4. D1-methylcyclohex-2-en-4-ol

Answer: A

The alcohol is the principal group, so it takes C-1. The ring is numbered towards the double bond so that the ene gets the lowest locants, 2 and 3. The methyl is para to C-1, which is C-4. The name is 4-methylcyclohex-2-en-1-ol.
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